“Tommy “The Hammer” Massis stops by to talk about how he went from a losing player to a winning one, plus thoughts on betting strategy, handicapping, and grinding for a living. Plus, a fateful elevator ride with Dyan Cannon.”
I know a lot of people have been waiting for this one and the Hammer did not disappoint. Let’s get right to it.
May You Win All Your Photos!
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You’re listening to the, in the money players podcast. Hello, and welcome to the, in the money players podcast. This is show number 19 Monday, February 25th on Peter Thomas for Nitel back with you in the Brooklyn bunker once again, and this is a show that spent a long time coming, a guest who we’ve had on before, but haven’t had the proper.
Sit down interview that this guest deserves. And I’m very happy on this day when regular co-host Jonathan kitchen is off traveling around the world to have this man finally in to join us for a proper session. I’m talking about one of the most respected. Can you believe, I’m saying that word about you respected and successful contest players around HorsePlayers around Tommy, the hammer masses, Tommy, how are you today?
The good morning story, my life story of my life. No respect. What was your first experience with gambling or the racetrack? Well, at an early age in gambling, I learned right away how it could be rags to riches, riches to rags. There was a local guy. I looked up the name. They would just say it was Gino, right?
And do you know, you see gene always have a Rolex or a great suit on driving a Corvette with like a Playboy model in his car. Right. And then you see Gino three weeks later with a Timex on a bicycle with $2 doors on the back of the bicycle, you know, wearing ripped jeans. And I say, Gino, what happened? He goes, yeah, don’t gamble.
So one of the first jobs that we had as kids in our neighborhoods, I dunno if you guys are there’s a game we played with rubber bands. You’d make like a skipping rope with a rubber band. It was called Yogi and the game you keep rising up and try to jump over it, hopping on it, trying to picture that, yes, you make like a rope with rubber bands.
You stick those thick rubber bands together, and two kids would hold it and you’d keep raising and you kind of kind of run. I run at it. It’s like high jump except you could step on it and get over it if you guys are. So we used to organize games on either end of this lane way. And we were told that when the cars, when a car came, everyone had to scream at the top of their voice car.
So because in the middle of the lane way, this was a crap game gone, you know, the end of the game to come and give us $5 each. And you know, so that was like the neighborhood I grew up in. Now, how did you take the lesson you learned from Gino and turn that around? How did you, how did you see, Hey, this doesn’t have to be.
The super high highs, the super low lows, or did you just accept that and want to do it anyway? Well, what I learned from him and other people to be on the right side of the game to be the house, you know, I’d started, you know, uh, running pools in high school, those parlay cards. And, you know, if I played crops, I made sure I was, you know, with the guys who were running the game.
And I went through most of my young adult life. Running gaming operations, you know, working on the house side of things. And I think that taught me the most lessons in gambling down the road to how not to gamble. What did you learn? How not to do from that situation working on the inside? What did you see?
What mistakes did you see all the time? Uh, guys, uh, doubling up when they were losing quitting, when they were winning. The guys who did the opposite, usually were the only ones who could win, letting your emotions get into things. Guys were getting mad and guys, you know, people would get other people mad cause they knew they that’s the only way to empty their pocket.
Alcohol, giving people alcohol’s a good way to go. Their bank role, you know, you just learn and learn and you start to learn. You start, it starts to sink in. What about the horse racing and the handicapping side of things. You’ve told the great story about your first day at the racetrack, seeing secretariat, bring us back there and tell us how that came about.
And was this at the same time as you were already volunteering to help out at these other gambling places or did no, this was, this was way before that I was just a kid and, and. Like my uncle, my cousin, and the guys in the neighborhood, they all liked to go to the races. I remember the first, you know, the first two times I went to the races, they were taking me to the zoo.
They were taking me to the movies and things like that. So the first time I went to a thoroughbred race, because the nighttime, the hardest races at night, where all the working stiffs, you know, went to at nighttime, they, you know, so Friday, Saturday, the odd Friday, Saturday night I’d get dragged to the harness, but.
Well, one of the thoroughbreds, the first time I ever made a bet, my uncles, I wanted to go home and my uncle said, I’ll make a bet. Pick a horse. And I bet on a horse called Kennedy road because there was a Kennedy road in Toronto. So the only name that popped up, and I remember him being on the lead the whole way and those black clouds.
And when he quit, everyone wore like they were cheering against me. It didn’t sink into me that they were cheering for this wonder horse. If I had no idea who, who it even was until many years later, that is hilarious. Obviously your uncle and those family members had an impact on you. There was something about the track more than the other forms of gambling that, that, that drew you in, or at least that’s what it seems like to me given where you choose to spend so much of your time.
Oh yeah. I love going to the, you know, I got hooked on it and, and Michael was my first actually, you know, my uncle never came close to making a living at the racetrack, but he was really my first teacher because. He would unwind, but he bought, you know, if he was up money he’d bet, 600 on a 30 to one shot, he didn’t care.
Right. And I learned that that’s where, you know, No, you got to have gutsy. Can’t be scared. You know, the first you’d say 630. What are you crazy? You gotta be crazy in this game anyway. You’ll beat the game. Well, that does seem to segue nicely. Jumping ahead into a little bit of a conversation about betting strategy and how you approach it.
But let’s put a pin in that. We’ll come back to that in a little bit. I want to talk more about those gambling operations for folks who don’t know. These, uh, from what I understand of the law up there, these couldn’t have been legal establishment. You must have met some interesting characters. How did you as a kid find yourself fitting in and were there ever times that you didn’t fit in?
No, I always fit in Mandarin in my neighborhood. It was a tight neighborhood. Everyone in your neighborhood could beat you up, but the guy from the next neighborhood couldn’t beat you up. And it was pretty tight. And there was, I was exposed to gambling from a real, it was all around me, even, you know, when we started going out at 16, 17 downtown, you know, right behind the bars, there was this lane way behind this hotel.
And there was a big crap game. And, you know, there’s all the elders, gene, all there’s all these guys, you know, it was called the, it was an after hours club called the two. And they had a crap game there every Friday, Saturday night, multiple crop kids, right in the lane ways. And you know, the police would come by once in a while.
And, and through things like that, my whole life I’ve been around gamblers my whole life. I was fishing for you to tell me this particular story. I recall maybe it was from a different point in your life, but when you got in a few moments of trouble over some comments you made about Frank Sinatra. Oh geez.
I was at a wedding. Right. And the guys at my table, no, they, they know the way the role. And I made a comment. I said, if Frank Sinatra wasn’t hooked up to the mob, he wouldn’t get a job singing in the subway, making pile. The table behind me was like the godfather of Serrano and all this. And they’re all getting the ANSI and this and that.
And my friend at the golf, he goes, the guy is nuts. She’s had too much to drink. Don’t listen to him. He just got out of the cuckoo house, no paying them. They started laughing and then shared that when I looked and saw who I was, I go home. Oh my God. What a time to tell a Franklin officer joke and a mob joke.
Pretty ridiculous stuff. That’s the same thing like bill Charlie, right. But Kelly wasn’t blind. He couldn’t get a job sweeping the opinions of professed by Tommy masses do not necessarily represent those of the, in the money players, podcast folks, but they are always entertaining to hear. I want a little bit more from those days, Tommy, whether it’s a specific story of something you saw go down or a lesson, you learn something to share from the readers.
I’m sort of picturing you in the, the spider role in, uh, in Goodfellas at some of these places in Toronto, there, there had to be some interesting stuff going down. No, not this fighter. Well, no, no, no, no, no. I was the brains. I was the brains all the time. The brain, I was the guy that they brought into. I ran a lot of these things pretty well.
And that’s where, that’s where I learned. I’ll give you an example of like certain gamblers. There was this one guy, crazy Joe and. Crazy drill was the world’s biggest chalk player ever. When we were first back, this is going way back in. We’d have simulcasting from the state and it would be two separate cool.
And this place was booking horses into the Canadian pool. So whatever the Canadian prices we saw is what you would get paid. Well, there’d be two horses at the metal lines that were even money. And he bought the one that was one to five in the Canadian. We could actually write a book about this two guys who died.
There’s only one guy left when he passes away. Then I can tell all the stories. Okay, fair enough. That’s that? I’ll take, I’ll accept that rain check and you’ve given us, you’ve given us some good stuff on that you talk about. I never wanted to write something where we can turn it into a pilot. I’m sure the guy who’s alive for, you know, certain.
The amount of points would be right. You’d be a creative executive producers. We call them. There’s plenty of, there’s plenty of that out there. I remember you telling me about a character called the black cloud who was active in your old time restraints. This is a great story. So it was guys named, we called them the block anyway.
The blacks, the type of guy that you know, was born 50 cents to make $2 and bumming cigarettes. And, you know, we call them, stupors looking for scratches on the floor. And so one day he comes up to me and he says, are you going to Mohawk tonight? I go, yeah, why? He goes, I’ll give you $20 for a ride. And I said, just like that, ain’t no negotiations, no nothing.
20 bucks. He goes, yeah, I go, what’s up. So nothing’s up. I’ll give you 20 bucks. I got no, no, no, no, no. I go, listen, tell me what’s up and I’ll drive you for free. He said, you know, those new Sam machines, I go, yeah, he goes, well, you know, fuse. Sometimes you go to cash a ticket and it comes out. I said, yeah, he goes, I’ve been cashing them.
I go, where he goes, and then it hit me because when you bought one ticket, say at aqueduct and went to Yonkers at night, the way they cashed those tickets back then is they had a book with the results. From the other track, there was like, no cross. Then take prompts, track tickets. So you did the guy that’s sick.
It he’d circle the date, the race, the bat, take out his calculator and pay you in. He goes, don’t tell no mom don’t do it. Don’t do it too much. Don’t get greedy. So this went on for a long time. I won’t say how much money we pulled out of there. Right. But it was a little bit over a hundred dollars. Let’s just say that.
And I told the black, I go black. If you ever get caught, just scream, bloody murder that you, you bought the ticket off. Someone else denied the 19.
So two weeks later, I’m at the track and my friend, little Tony comes over and I go, what’s up Tony? He goes, Because security is upstairs killing the black. What do you mean? They’re killing them. Listen to this, this guy scream, he’s screaming, bloody murder. He won’t stop. They’re dragging him out. He’s screaming and screaming.
Right. And then I hear it and I start, the it’s getting louder and here comes to security. They’re walking the blackout and he’s screaming and he’s looking right at me and I closed my eyes. And as he came close to me, he winked at me and started screaming even laughter. Needless to say, they let him go. He just, she wanted to Sue them to get his money back.
He said, he’d got tickets off a stranger. How quick did it take them to rectify that toad issue and whatever happened to your man? Well, I don’t know. Probably it must have been about a month before they figured out that they were, you know, the books then balance, see back then there was no cameras at the track.
There was no, you know, It was the wild West more or less the early days he was on the we’re on the circuit, going from Woodbine to Fort Erie, from Fort Erie, to what, you know, that situation was obviously unique. How were you making your money back then? Or were you just more hanging out at the track and working somewhere else?
Yeah, I don’t know. I was doing whatever I could to make ends meet. I didn’t last long I jobs, so I just try to hustle whatever I cook. What was the last street job you had? I was a courier and I li like, uh, did that for two years. The last year I did it without a driver’s license and I was making like 1500 a week cash.
I didn’t want to give it up. But then one day I woke up, I phoned and said, I’m joining the circus. I quit. That’s where I went to one of those other job opportunities, really. And what did happen to, uh, the black cloud in that story or the black? Yes. He’s still around. No, I haven’t seen him. Cause, cause what happened is that he was an East ender and they, they, uh, tore Greenwood down, right?
The Torah, the Torah Greenwood down everywhere. I am everyone like stayed at Greenwood day and night for the simulcasts. And once they tore the track down and made it a small little simulcast area. Like an off-track betting. Only the spenders went there last vendor from Toronto. Gotcha. Gotcha. So I haven’t seen him in years.
I don’t know. He’s probably smoking crack somewhere, not to put too fine a point on it, but that does sound like a potential outcome. Let’s move on Tommy. Let’s talk about bedding strategy. I think you’ve given us some hint. As to how it evolved. I’ve heard you referred to as the walking kill bat, that concept that came up in the Mick Maloney book bedding with an edge where he always takes a certain portion of his money and just tries to murder the race, betting cold numbers and, or his strongest opinions.
Just a little bit more to really be paid when he’s right. Is it safe to say that you take that concept to another level? And where did the idea evolve for you? Yeah, I understand. And see what Mike does. Mike, I would say is in many ways more conservative, conservative than I am not talking politics, you know, and the way we approach the game and probably life not to say he’s conservative his approach of life.
I read that book, you know, it wasn’t a conservative, but compared to me, so when the differential main difference, different thing is the way it just said. Just say he. Makes that kill bet with a small portion. Let’s just say his, his bed is a hundred dollars and $10 of it is the kill bet. Well, what I do is make hand $10 kill bets.
I’m a guy who bets. I only bet one track, but I usually bet every race. I usually bet like when I play Woodbine, I’m playing every pick three, everything for every pick five and I’m trying to kill. And to me, the only way you can really, you can’t just sit there and wait a week and spot, play a kill bet. And I learned that I read that, that actually they, they wrote they’ve good friend wrote that once.
And it kind of, reinstilled my thoughts about it. This is a long time ago and it’s to, to hit home runs. You got to make a lot of bets. You just can’t sit. And, you know, you can sit and scout out a horse and get a $5 horse. But if you want to get a home run, you got to make a lot of bets to hit that. You know, anyone who thinks it can cope talk, uh, pick three that pays $400 or $300.
No, you just got to make a lot of bet. So I think that’s the difference in our approach where he’ll bet a hundred dollars and 10% of it will kill will be a kill bet. Well, I will bet, you know, 10. 10% kill, but it’s interesting. And I like the way you bring in the idea of betting more races, thus giving yourself more opportunities and hopefully diminishing the length of losing streaks.
I mean, what I fear if I were to approach life and gambling, the way that you did. Is, it takes a lot of fortitude to deal with being almost right and not caching. That’s something that must happen to you frequently. How do you deal with the inevitable losing streaks? There is that, that hump that you have to, when you do make that score, that second score, the third score.
And after that, it’s easy. But before that it’s hard, man. I get it. I get it. People get sick, you know, like kina six, seven, the one shot spending 300 and getting nothing. He wouldn’t buy 10, you get nothing that would drive people crazy. But you just, I, I. Got to the point where I know sooner or later I’ll get them sooner or later I’ve got him.
So I don’t, I just let it go. I let it go. You know, like going to that old thing, you know, you can, you can be or race, you can’t beat the regular, you can on race, but how are you going to pay for your gas in your program tomorrow? So you beat a race. Like, you know, you have to try to beat the racist. If you want to make a living at this, you can be, I mean, when can beat a race, big deal, but you can’t win, beat in a race, you know?
That’s the one thing always say, you can beat the races, but you want to count on just beat in one race. Even if you do, what do you do? Where did the style come from? I mean, were you always this way or did it creep up on you? No, me, my, my big gun was 17 across on a six to five shots at the $50 window.
Right. That’s the way I learn. And then someone, someone told me, he goes like, And I just posted this on Facebook today. Cause uh, there was somebody put up a discussion on one of the sites where people are trying to learn on the back wind place. And all I said is, you know, I argued a bit and then I said, Hey do this for what I did for a month.
Every bet you make at the same way, that’s what the guy told me. It goes by right down, which you would have got for two across three win place or six to win. And he said, I assure you at the end of the month, No, you’ll probably be negative in all three columns, but the wind bet will be the least negative and he was right.
It wasn’t even close. So that was it for placing show for the rest of my life. Well, you know, I would do the same thing. I would bet the 25, you know, the bombs in place. And then someone said to me, he said, you know, w w and I posted this today too. Like, what does an average place price pay on a 25 to one shot?
I said, around $16, he goes, so you bet to win place. And he goes, you got, you got three to one on your money. And I go, what do you mean three to one six? He goes, yeah, your button $4. If the horse comes second, you’re getting three to one on your money. If he wins, he got in 25 to one on your money. I go, then that’s out.
I never better rent place again in my life. Simple things to be explained the right way. Right. And it’s like the worst mistake gamblers do was trying to win a race or survive the day when, to the day. I get it. If you’re, if you’re working, if you have a good job then, and you know, you could break even in the long run.
Right. That’s a great thing. I get it. But I’m not trying to do that. I’m trying to win and I, and I’m trying to look good winning. That’s interesting that you say that I wouldn’t have thought that you cared about the style points. What do you mean when you say you want to look good winning good. I just don’t want to show that I’m pleased.
Gotcha. Okay. I didn’t understand, you know, I want to make a living. I want, you know, I don’t need a Ferrari in a big house, but you know, I want to have a four month vacation in Florida. I want to get new shoes when I want a new TV, you know, in 2015, when you won the breeders’ cup contest. I remember you telling me, I don’t know if you were exaggerating or not, but that when you made the big, bad, I’m trying to remember.
I think it was a, was it a $4,000 exact the box? Four on the winning combination three on the saver combination. So you had, you had 7,000 in play. You told me you didn’t have a, in, at the bank account back home. At that time, you didn’t have that much money. I broke. I had $40 in my pocket. 20 was for the waiters that Caitlin and 20 was for the maiden, the hotel.
And I was broke. And the race before that, I bet I bet 13,000 in the sprint then law. So it’s safe to say that you’re at 25,002 races before that. And I would have lost it all if I. If, if I didn’t hit, that’s amazing. But it sounds to me like your risk tolerance, much higher than the average person that must play into your ability to do this.
Yes. Listen, I used to be one of the sickest dogs out there and I got here and I just pull it out when I really needed. And the odds are right. Yeah. That’s interesting. Where did, how did you get cured from the kind of compulsion that sounds like you’re referring to. Well, cause when I got home one night, right, there was these two big guys and my mother said, that’s him.
Those were the books. He didn’t either. So this was when you were a young man, you had the T you felt you had that running through your veins. Yeah, the first time, the first time my mother bailed me out. Right. She said never again. The next time. She, she, that they didn’t that stories, but they phone and I heard my mother go, listen, you just can’t, I won’t be here.
I’ll tell you when he’s home, we would do this. Who’s going to hold them. You can hold them down and I’ll break his legs or I’ll hold them down. You break us. Like, that’s what my mom told them. And they actually liked that and laughed and told me, listen, your mom’s a nice lady. We’re going to help you out.
You can come and paint here and do this. And I, and I never did it again. I back cured me. The fear of taking a beating, cured me of my sickness. That’s amazing stuff. Have things changed. Are you still as up and down or was that a real sea change in 15? Do you feel more stable and you’re gambling now or are you, are you a couple of bad weeks from being at the edge potentially finding no, I got, I got, I got down, you know, down to.
Not so a couple of weeks, but to where you start thinking of, Hey, and then I hit one day I hit for like 240,000. This weekend. One Sunday was just like, it was an unreal day on unreal day. And out of that half, one 40, 70 wasn’t mine. But the rest of it was mine. It was like one 70. I made a one day. And that basically, you know, and plus that plus I’d been doing well with owning horses.
Yeah, I wanted to ask you about ownership, but we’ll, we’ll get there in a minute. What was the best day you ever had at the track? Was it the breeders’ cup contest was that this day you’re referring to, what would you describe as the best day? That’s an easy and it’s neither. And it’s nowhere near that amount.
Going back to the days where we were just out of high school and going to the track and be meeting my friend Carlo and little Tony, and we’d go everywhere to gather. And you know, like basically when one guy hits, you would give. 25% of his hit to the other two. And, you know, we were just playing, going around.
We’re going to the tracks, smoking pot and having a good time and no worries, you know, going all to be tracks. So when they were at Greenwood and Tony was out of action for a while, I didn’t have no money. It was just me and Carlos. Parallel goes to me. He goes, how much money you got left? I go, I got about 60 cents.
He goes, good, good. Give it to me. He, why? Cause I got like a buck 50. We can make a bet. I go, yeah, handed over. I go, you know, who’s in. So I still remember, we bet $2 to win on. Doug Brown was a harness driver. We got like 11 in chain. And then I bet Flamborough I did my famous one to all bet and I want to box and it’s one that they were like four to one and six to one.
And, uh, like the one to two shot is parked on the outside and he’s life and death. And it came one, two, and there’s a three horse portal for third. And somehow that favorite hung on and we were all upset and we cash like $23. So we had enough and I got the program we’re sitting there and just hanging out and bought the program for the next night.
And they’re like in 10 seconds, I handicapped to pick for it. The drop. And it hit me. I can’t go, I have something to do. I couldn’t go the next day I go, Carlos, you’re going tomorrow. And he goes, no. So I go to Tony, Tony. You going? He goes, I don’t know. I go, listen, I’ll talk to the guy. I’ll get you a dime on buying the pot on credit.
Just come. Here’s the 20 betters to pick four, keep the $4. We hit 18,900. With that started with Jane. We basically like we, me and Carlo got like, we took, like, I can’t remember. We took like 7,000 each and gave Tony, Tony the other 4,000 and back then, like, I didn’t even know what to do with that money. So I got home and I basically took 200 out and gave them most of my mother.
That’s great. Mother goes, what did you do? Right. Well, I hit a race. How much did you hit? I go, this, she goes. Well, the time you use your head, right. You know, like I was actually one of the tracks with $10, you know, borrowing 20 bucks from my mom to go to the track. Right. The end of that story is that the next day, the next day, when I get out, I come home, I go my room, it looked like a tornado.
Hit it. I go, ma what happened? Did we got robbed? She goes, no, you gave me 7,000. I figured you had about 80,000.
Yeah, I go, no, that’s all. I kept 200 rides. She goes, where is that? I go, I got a hundred. She goes, you’re a good boy. That’s amazing. What did she think of the gambling lifestyle? My, my mom, my mom gave me the biggest life lesson in gambling and like she, of course she didn’t like it. And after I got to the point where she saw it, she always said, don’t work in gamble one or the other don’t work in gamble.
They don’t mix one or the other because I had jobs, you know, friends will get me jobs. Payday broke. Next week payday broke and then quit. You know, what’s the use of, she always, I don’t know, you just don’t go. Right. And she said it, you know, when she was, you know, before she passed away, she goes, you know, I was working for a friend in the restaurant.
She goes, nevermind, nevermind. The working in the restaurant, focus on the gambling. Cause no, he was going to work and be broke. He might’ve all just be broken. You’re going to be broke. You know, I ended up being a real good lesson and, and I saw it, you know, in practice. I was making big money working and never had a penny and lost my job or the place got closed down.
And then, you know, I got like 60,002 months of all the good days that you’ve had. I think it’s interesting that if you choose one that hearkens back to this other era of your life, why do you think that feeling even now stands above all? It’s just that, that day when I hit that race, other than it came from pennies, and like I said, $20, $20 was enough for me for.
A day at the track, you know, I’d get a slice of pizza for $2 and we chip in on a, you know, smoke some reefer and have, you know, put in five, six bucks the bet with that was a lot of money and that I gave it to my mom and, you know, Both points lost that a long time. You’ve mentioned the casual drug use. I assume, having been at the bar with you and seeing you order a Shirley temple, that at some point you gave up the drinking and the, and the smoking, especially when it came to gambling, but maybe in life in general, is that related to some of the discipline you found later in life?
I don’t know about casual. Keith Richards has got a heart attack hanging out when I was at my friend.
That’s actually the story that I’ll tell you this. I got, I went to that guy. I blew up my back in 2006 and really was, you know, in a tough spot. And. Really taken a lot of painkillers on top of 2008, I got myself clean. Totally, totally no weed, no nothing totally clean. And I was doing good for about six months within these to try not to use the name pieces of it garbage, you know, they said, Hey, we haven’t seen you for a long time.
It goes to one of you wants you to come over. We’ll go for dinner tonight. I go, okay. But I’m not one of the track, you know, they’re a race trackers, right? No, no, we’re not going to the track. We promise. So we didn’t go to the track. They bring me to an off-track. And the first thing that guy does is throw like a throw is a program.
I had him bet on a horse in six months, I couldn’t function, you know, losing my mind, throws me some wins or harness program. And I had 60 bucks for dinner. And I lost like $24 into it, you know? And I was mad. I was steaming. I told him, I go, you guys are paying for dinner. They go out or whatever, whatever.
And they got, they’re laughing. The guy throws me on Northfield park program and I go, what the hell? So I I’ve got $36 into it. It happened to be a carry over to daycare you over. And I hit the thing. I keep a guy named Keith Cash only because of a story. I met a friend of his in Toronto named Stanley Stein.
And if I don’t keep the cash was still driving and Stanley Stein told me something that big me single Keith Cash, and that’s between me and Stanley, who’s gone a long time ago. Fair enough. And this thing comes back 15,000. And I cashed 15,000. I remember going up and cashing the ticket and getting 600 and throwing these two pieces of garbage 300 each ago.
Here’s 300 each.
Okay. Change my life because it got me back psychologically. Right. It got me into a place where we’re saying, yeah, you quit, you quit the drugs. Okay, forget about quitting the gambling. You can still do it. You know, like I really never looked back. I had some lows ups and downs, but you know, even, even when I went into the breeders cup, that time broke, I went broke because I spent about 80, 90,000 in Florida in three, four months, divide time between the two you’re talking to us from the Florida home.
Now for, for folks who don’t know quite sensibly issuing the winters in Toronto. But we, for a time you were worried that the addictive stuff. Was could be potentially a problem for both, but as it turned out, you figured you could do the bedding in a responsible way and still leave the other stuff behind.
And you haven’t looked back since, is that an accurate representation? Yeah, I’ve been basically profitable every year and the only time I came close to broke, I was almost empty at the end of 15 it’s because, you know, I was making my money at Woodbine and then Woodbine ends and. I’m down in Florida, spending money in Gulf stream was, you know, and I had some, you know, the same time my uncle was dying in Toronto.
My head was all screwed up and, and it was a rough time. It was a rough time you saw when you interviewed me the breeders cup. I was in tears, man. I was, I was shattered even though I won it. It was an amazing interview. Uh, I’ll never forget it, Tommy. I didn’t know obviously what to make of you. You, you, we didn’t know each other well, and at first you were kind of like, maybe I’ll give you an interview, you know, interviewing me, you came, you pushed me for the last race.
I told you, what are you out of your freaking mind? I just wanted to say hello. I wasn’t asking you questions or whatever. I said, what are you crazy? No, that is not what I would’ve been looking for. You it’d been interviewing the winner with, with your camera’s cord around your neck, but I was very surprised the next day, when you told me the story about your uncle and, you know, just so genuinely moved and emotional about what he meant to you and what, and the great line.
I think I asked you at the time, I said, what would your, uh, What would your uncle say if he heard that you won all this money and you said something to the effect of, ah, he told me I was, she’s going to blow it all out anyway, you’ll go broke. Anyway. Definitely reminds me of the kind of, uh, uh, family bonds that, uh, you hear of in these, uh, Italian.
It seems like a lot of stories in Greek, Italian and Jewish families with, with relatives like that. My uncle was the type of viewer down. He picked you up a viewer up, kicked you down. You only prayed. He only prayed on the strong, very obvious to me that the mental part of the game is super important to you.
And in your success from the stories you’ve told, what advice do you have? For other horse players looking to get stronger mentally to deal with all the crap that we have to deal with. As HorsePlayers, don’t complain, just do something about it. It’s like, look at this garbage that’s going on in Kentucky.
Don’t give them a dime of your money. You’re not happy with the takeout. Don’t give them your money. Find somewhere else to find something, you know, like we, we don’t have, look, I jokingly bash Hannah, right? And kind of not, but listen, we need a horse players, union, a serious union, you know, so, you know, a group of guys that really want to get in people’s faces and you know, a group of guys, I know it’s going to be impossible because people are sick, you know, sick in the head and they want to gamble so much.
That’s to try to keep them away. But you know, somebody, you know, as horse players, we could teach the Stronach group, Churchill, Nairobi, whoever else, Woodbine, we got all teach him a lesson. Or we’re too sick as a group. And I’ll include myself in that. You know, I’m not totally, well, I’m still a bit sick, but you know that we should, we should be able to get together and kick their frigging teeth in.
But I remember happened cause cause it’s just such a disease and people don’t care. They just want to play. We get pushed around like the biggest schmucks on the planet. It’s powerful words. And I think there is some truth to it that at some point people need to stand up for themselves. There’s so much we have to get to.
And not that much time. I wanted to ask you one handicapping question. When we’ve talked about in the past, you’ve definitely identified your trip, work as a key to your success on the handicapping side, coming from the world of harness, as much as you did. Are there lessons that you learned handicapping those harness races back in the day that you still apply and what are they?
It harness, everything was up and acute. In other words, angles, we didn’t have replays back then and I was too high to keep notes. And you know, that that was all, that was all pleasure. If you really want it. The guy you had on a couple of weeks ago, uh, from new Orleans. Oh, Franklin. He’s great. Yeah, they’ve been similar kills me all these horse players.
My goal, we heard bake-off they got, you know, from, from Louise’s they got these horrible names. Cool name like
roaches. We’re going to have Eric. We owe on next week. I don’t know if that counts, Eric. WEO the trainer. Oh, okay. Know another sad name.
I’m kidding. I’m kidding. I’m kidding. I know, I know two of those guys that I love them, so I could no offense to Frank who I’ve never met.
what Frank said. And I’m going through, I go through that, that he watches the replace, right? And you watch it and you can’t slip up. You can get behind. And that’s my, that’s the one thing that I fault, you know, that hurts me. I’ll get behind other things will come into my life and you get a bit behind you.
Can’t you gotta just keep plowing along, following along. And, and what I mean is I don’t not do them, but I noticed where I get lazy and don’t, you know, And like I was listening to him and, you know, he was, it was entertaining. I read that it wasn’t, but that’s the whole thing, you know, watching those replays and sticking to, you know, what works and you just gotta stick with it.
And it’s not that hard. It’s not like for, you know, we’re, we’re breaking breaking stones, but it’s still, you got to stick to it. You know, sometimes you gotta just say, I can’t go out. I got to catch up and. Those things were beating me when he was talking. He was hitting me over the head because I’ve been kind of doing that down here.
I got a nice, nice head start here at Gulf stream. I was up good money and then got lazy and paid the price for it. And I stopped playing. Are you waiting for Woodbine at this point or, or wait, what am I waiting for? That starts in April. You, you are, you have called yourself the King of keen Lynn. We often talk about the Prince of keen land on this show, but you have referred to yourself as the King of Keala.
And frankly, you’ve earned the title with three wins there in the last few years, whether I learned it or not, they treat me like royalty and I’m sure I’m not the only one. What do you like about it? I can phone the hotel. Right? I haven’t been here since October I’ll phone, the hotel, Monday to Friday afternoon.
And Jean at the she’ll recognize my voice. She’ll say Tommy that’s at the hotel at same thing at the track. You know, whether it’s, uh, Mr. Goodman, who I loved, he was like my second father Misty, Jesse. You know, the people that opened the doors, the same people that recognize your, I love it there. I love it.
I love it. I love it. I love it. And have only little to do with winning. There’s always great, but I just love it. There. We talked before about being in a good mental state, clearly being important to your success in all horse players success. I can’t imagine you’re in much better mental state, anywhere than sitting in that green room at Caitlin, where you’ve had so much success and you meet you’re made to feel so welcome.
Oh, I it’s, it’s crazy. The feeling I get when I walked in there. Right. You know, like there’s, you know, I lose my mind, but you’re like, I’m so pumped up and so confident, you know, like these young football players kind of bumped into me and I said, Hey buddy, when’s the last time you have your heart stopped?
You know, like you start feeling, I’m going, what am I saying? Shut up. You’re going to get killed. No, it is. I walk in there and I feel invincible. It’s scary. It’s scary. It’s scary. Look, I’ve won. I’ve won money and earned it, but it’s scary how much money I took out of there that I didn’t earn that. I don’t know how I hit, you know, Weird things happen there.
I want to ask you about tournaments. I know you have strong opinions about how they should be running. I want to give you that, which I don’t necessarily agree with, but still want to give you a platform to give your views. But I also want to know how important tournaments are to your sort of overall business plan as a horseplayer.
Maybe we should start there. It’s always been other than when I, when I was chasing Jonathan, right. And for that couple of months where I had a shot to make some extra money, it was business and I didn’t enjoy it. I didn’t like it to me. It’s always been part of my vacation. I don’t take it seriously. I’ve been so lucky and fortunate to win what I want, but I write it off as an expense.
I do well at it, but to me, it’s just part of my vacation. If Caitlin never had a contest, I’d still be going around the thing either that week or the week after. I love it there. And the contests are not my focus at all. I, you know, I got the membership for the NAC when it came out for $25 near the end of the year, I went to Del Mar with a bunch of friends and.
I was told that I could, I could, if I won the NFC spot, I could, the client didn’t get a Del Mar spot. That was fine with me. If Keegan, if Caitlin would’ve gave me a $3,000 buy to their April contest, I would’ve declined that spot too. I tried to sell it. I try to decline that to the guy who was on the bubble.
And I said, make me any kind of reasonable offer. I want to put 3000 in a heartbeat. You just feel like you have no edge in that Vegas contest for a minute? Well, it’s a crap shoot. I, you know, if I get hot, if I get hot on that weekend, I could, I can make, you know, not 800,000, but I could make a couple of hundred thousand.
I really had that kind of a thing. But I mean, I don’t like Vegas. I don’t like blowing black, you know, roulette out of my nose for red, green, and black out of my nose for a week after. Every every so many people were sick, leaving there. I’m one of them. And I wasn’t really sick, but I, me, I got a paper cut.
I go to the emergency. I have no tolerance for pain at this age or anything. It was horrible. Wrote my kid. Brother’s there. He’s got this thing where they, you blow the water up your nose, right. Excuse my language. But like it’s horrible. I hate everything about it. No. Like if I, if I went in to, you know, I’m going to Keeneland and play in April, if I win there, Oh, I’ll go again, but I’m not going to enjoy it.
I was talking more about live bankroll contest, but I’m glad to give you a chance to opine about the NFL. You, I want to know something. If I do actually did come up with a new strategy for the NAC. If I do go in there, I’m just going to pick, like, what was it? The 10 men, 10, 10, and eight, eight, 18 races. Yes.
I’m just going to give myself 18 mandatory races. Interesting. The eight, they give me an 10. Cause I noticed when you focus on those mandatories, you know, you know, you focus more on the race because you know, you have to bet that race, whereas for your option or you’re kind of flipping through three, four, you know, How will you choose the races?
How will you choose the races to give yourself as a mandatory, what sort of criteria? What’s like a dream Tommy Massis race to take a shot at? Well, for, for me, it doesn’t matter, but for a conference like this, it’s just going to be field sides. Right. And the tie breaker being one track over the other track.
Gotcha. So if I have kind of horses at the fairgrounds and 12 tamp, I’ll take the fairgrounds. If I got 10 horses that Oaklawn and tenets on Anita, I’ll take Oakland, just, you know, something like, you know, or even 10 and eight, you know, I’ll rent tracks, but just basically just spend five minutes and say, okay, these are my 10 optional races and that’s it.
Throw the rest of the races in the garbage and just focus. I want to talk to you about your horse ownership that came up before Calico racing, stable. How have things been going? We’ll start there. Well, it’s good. Me and my partner, Gary McMaster, uh, we were going to claim a horse that I wanted to claim September 17 and we got all shook for the horse.
We had the money in the account and I brought up two horses. So Monday, you know, one was for 10 and one was for 20. I go let’s. Take one of these. I prefer the 20. He said I prefer the 10 and we ended up taking both of them, a horse called thunder point who the 10, he win twice for 16, come third for 25. And then we blew them out for 7,500.
He went three for four and we lost them for 7,500. The other one giant storm we claimed for 20 made like about 150,000. Was that an 8:00 PM five wins, five seconds. I like 13 starts and a year. And at the end of last year, he fractured assessive Moines. It looks well. Yeah, he survived. He survived and he’s, uh, stall rest probably got another three, four months stall rest.
And then definitely not going to raise them. We’re just going to, I’m going to send them to a good retirement. You know, the vet said, you know, if he recovers this and that, but now he made too much money. And too good, you know, and he was a sound, sound horse, man. And he was just getting better and better every day.
So that’s, I’m just happy. He’s okay. Or else that, that would screw my head up. And then we claimed one in September of this year, a horse called claimed him for 20 off a race where he was basically pulled up, kind of caught somebody with their hands in the cookie jar. I kind of told Gary, next time the guy will drop and put a jockey on, but as money and we claimed him and become sucked in and a $40,000 purse, we win the $40,000 purse.
We went a $60,000 pot and we brought them to Oaklawn and they’re running there for like 90 GS. And he’s got a second and a third and the non winters have two cash and checks. But I tell all my friends like, well, if I ever asked you to come into the horse, this was before they go, no, I go, come in. I got something going or making money.
I’m, you know, I’m finding these horses. I’m being patient is a good investment and I won’t ask them twice, but you know, I’ve never pushed anyone into this game, gambling or owning. And now I mentioned, I mentioned to everyone, I go, man, I’m looking for a horse right now. Go scream in Oakland, the bank, the Toronto, if you want to make an investment, I think it’s a sound investment and to each his own, but I won’t push.
I just mentioned it once. So any day now I’m going to. Before I leave here. I’m going to come back with one or two from either here or from here at Gulf stream or at Oakland. I know that thoroughbred retirement’s important to you. That dovetails nicely with me pointing out that this show today is actually sponsored by the thoroughbred retirement foundation, our first sponsor, or one of our first sponsors to come on board here on the, in the money players podcast.
Difficult question for you. You are an animal lover, not just horses, but, uh, but cats, really all animals that I’ve ever seen you around, you seem to have a rapport with. Is it ever difficult to reconcile being involved in the sport of horse racing with your love of animals? Okay. First of all, I have a non-profit place about an hour and a half to Toronto that I sent all my horses to, and this lady rehomed them.
And even that I give her money. It’s a place called freedom Valley. And this lady basically it’s at the, say she in Ontario, we still sell horses for meat legally, and she tries to outbid them and housing. She’s got this farm, her and her husband. I don’t feel bad. Any horse I have with an issue, I get the horse sound.
I get it up to her. I’ve retired, Don horses up there and. It’s the one who wants to reach out to me, you know, in Toronto $500, the horse I’ll make sure that it has a good home and ask for, to, to answer. Your other question is like, if you can, if you can, if you see what horses, a horse being taken away from his mom acts like, right.
If you can handle that, don’t worry about the racing. Well, I understand why people are against racing. But one thing that drives me crazy, I, it older and everyone, all the bleeding hearts and heroes, the saviors of racing in the Twitter sphere, retire him, retire, retire them. We think they’re going to French.
Riviera people don’t understand these horses are being fed and taken. Sure. Some of them go to Oldford. It’s a big place you mentioned in the one in Toronto, you know what happens to a lot? People are crazy. You know, don’t worry horses on the racetrack are the furthest thing from my it’s what happens after race.
And like I said, if you can handle the horse from its mother, you know, if you can look at that and that not scar you for life and needs, no problem. They’re in racing. They’re there to race. They have a fun, they have a life, like I would never do it. That they’ll take a film, see what happens, but don’t find the home.
It’s a terrifying thought. And it’s a reason why organizations like the TRF are so important to support, but I’ll tell you this, Tommy, I don’t think your attitude is really that different than the people you’re seeing saying that on Twitter. I think there comes a time as you’ve acknowledged with your own horses when they’re.
Careers are over when they’re there. They’re clearly on the down swing and rather than risk them getting into the wrong hands, especially if they’ve made a lot of money for their connections, not everybody’s doing what you’re doing. Very few people really are doing what you’re doing. So I think want other people to live up to the standard you’ve set for yourself.
That’s what I’d say, but you can’t, you can’t. In to quote Jonathan’s kitchen in your mother’s basement and come out on Twitter and take shots at people in situations that you don’t really know. And I’ll give you an example. There was a Queen’s plate winner years ago called Boehm Paco, and he come back and he was running and claimers after like two years after winning, you know, being retired.
I couldn’t believe in him going this breeding. No good. You know, so-and-so and it bugged me for years that trainer, I thought the worst of this guidance at all, never met him fast forward. Another few years, my, my spot at Woodbine racetrack, I’m sitting behind him every day and I asked him, I said, John, do you know what happened with bum PayGo that time though, not you too.
He goes, this is what happened. Cause I have a farm with, I keep all my horses and this, this trainer owns a lot of horses. He started feeling good. He was chasing everything on the farm, any horse that was galloping, he chased them and race them, challenging his two-year-olds his three year old. And he goes, I have to get it out of him.
And he did, he wins, he comes second and then he come forth and he back in retard, but whatever, knowing what’s really happening, we should just shut up mind your own business. And, but they’re taking care of it. Now, if you know something. You know, like the garbage cans in, uh, where was it recently in Louisiana?
That’s one thing, but just to, you know, I’ve seen it over and over and it’s the same people in Toronto on Twitter trying to be the heroes of the game or one of the end, they pick their spots. Why doesn’t this person retire this horse? And then someone claims it, they shut up. They don’t say nothing, then someone else.
And then they pictures. Like if you really don’t know the story, be quiet, they’re getting fed. They got a home and it could be a lot better, but it could be on awful lot worse. I’ll say this for folks who don’t know Tommy, I mean, this, this is coming from the heart and it might be a different perspective than a lot of people have, but he really loves animals.
He loves horses. Yeah. No. Hey, quit racing. If you want to outlaw racing, I understand I’m with you. Make sure we have a place to put all these horses first before we, you know, let’s not go there. That’s a whole other podcast and one that that’s a complicated issue, but you do, you do make an excellent point for those at the extreme.
Who might have those kinds of views nobody ever thinks about what’s going to happen to all the horses in, in any kind of scenario like that. But anyway, yeah. Yeah. Nobody just thinks period, sometimes on Twitter, great organizations out there, and obviously I’m beholden to and loyal to the TRF for the great work that they do.
And if you’re not like Tommy with skin in the game, or you have your own horses to take care of donating to an organization like TRF, I mean, look, HorsePlayers give a lot already. I know that you know that, but I just feel like it’s the right thing to do to try to help these horses in retirement as well.
And that’s coming from the heart from, uh, from my direction this time. You’re a hundred percent, right. Instead of going on Twitter, make a comment, send a check before I let you get out of here. I’ve kept you over time. But before I let you get out of here, I want to talk to you about food. Your favorite places to eat in Toronto.
Okay. California sandwiches, veal on a bun, hot peppers, provolone mushrooms. We have the greatest fish and chip shops on the planet. Two pieces of halibut were fries almost anywhere in Toronto. One good one neighbor named one. Good one. And I’m really just asking this for me. Forget about the listeners. This is just me.
I knew we needed to do fish and chips next time. Yeah, no for sure. But Pella for, have you done California? We haven’t done it yet. You’ve told me about it, but it hasn’t, it hasn’t come on yet. If there’s a place where you can actually go into Toronto and say, without a doubt, this was the best deal sandwich or.
Sausage or steak or chicken or egg plant with all the dope. If you eat there, you’ll say this is the best thing which I’ve ever had at poly and sandwich I’ve ever had in my life. No doubt about it. There’s not anything like it anywhere on the planet. I just paid to hear you say that word over and over again, Tommy.
Which word is that? Well, I would say sandwich, but you say it a little different. I like your way better. How about if I’m bleeding,
great stuff. Any other plugs you want to put in for, for dining? I know there’s a lot of great stuff up there for dining. No, I’m just giving a shout out to the chocolate Buster who I drove crazy in Vegas. My friend, Mike Barker, you got to get them on. He’s scared to talk and then you’ll talk in person.
He’s a great guy. You have to get him on. He’s a great handicapper. He’s on Brisbane at or whatever. Well, the Churchill group, whatever they call themselves, you got it. You got it. That’s interesting. I drove him crazy. I was trying to try to find a school, right. And I can be annoying you Tommy. Thank you so much for your time today.
We’ll have to do it again soon, so much. Great stuff, and God speed out there. Go get them at Keeneland and beyond. Thanks, Peter. My pleasure. And there you have it. Tommy, ladies and gentlemen on this edition of the, in the money players podcast. That’s it for show 19. I want to thank Tommy one more time.
We’ll thank Jonathan kitchen in his absence. We’ll thank our friends at the thoroughbred retirement foundation. 10 strike racing. Most of all, I’d like to thank all of you. The listeners, we will be back on Friday with Jake Ballis of black type thoroughbreds joining us until then. I hope you have a great week grinding away at this crazy game.
We play I’m Peter Thomas foreign, a towel. May you win all your photos.
What’d you have for breakfast? I had scrambled eggs with provolone, cheese and musical licks, all of bread from whole foods toasted. That’s a very detailed answer. Usually people don’t hardly remember what they had for breakfast. It’s very healthy to cook. I may save that and put it at the end of the show.