Keeneland Grade 1 Gamble Overview – April 10th, 2021

As luck would have it, I qualified for the Keeneland Grade 1 Gamble this past Saturday on HorseTourneys.

At this point, on-site participation is full but you can play on one of several ADWs – XpressBet, NYRA Bets, 4NJ Bets, and TVG.

The entry fee is $3,000, with $2,000 going to live bankroll and $1,000 as an entry fee to fund prizes.  You’re required to wager a minimum of $400 in at least five races at Keeneland.  The final prize pool will be determined based on the number of entries but it’s expected that as many as six BCBC seats and 10 NHC spots will be awarded on Saturday.  That’s in addition to cash prizes that will be awarded to the top 15 finishers.

There’s still time to enter.  If you’re playing on TVG or 4NJ Bets, you’ll need to register before noon on Friday, April 9th. Horseplayers using XpressBet or NYRA Bets may enter until noon on Saturday, April 10th.

I’ve played in the Grade 1 Gamble at Keeneland several times over the years without much success.  If I’m being honest – and my records confirm – I’ve never had much success at Keeneland, even outside of contests.  But like many, Keeneland remains a special part of my horseplayer story.  After all, it’s the place I was first exposed to horse racing on a Saturday afternoon in May of 1998.  Having no clue what I was doing, I picked three horses for the Kentucky Derby and my neighbor made a $6 wager, boxing them in a trifecta.  Real Quiet galloped home a winner and my three horses completed the trifecta for winnings that totaled just over $600, if I remember correctly.  My mom wasn’t impressed, mostly because I was underage at the time and it required her to claim the winnings on her taxes. I digress.

As I prepare for the contest on Saturday, I wanted to do a bit of digging and understand what it would take to win and perhaps just as important, for a player like me, finish in the Top 6.  The appeal of the Keeneland contests, for me, is the number of BCBC seats that are in the prize pool.  That’s my goal in this contest – to win a BCBC seat. Others will be gunning for a Top 10 placement which is projected to land a spot at the 2022 NHC.


Saturday’s card has been drawn and unfortunately, the forecast doesn’t look ideal.  I haven’t handicapped the card and certainly haven’t committed to a strategy, but there are some things worth discussing.  Let me also caveat this by saying, you might completely disagree with my assessment here – that’s fine, though I’d appreciate your feedback either here on this post or on Twitter.

Finding records of past results of the Keeneland Grade 1 Gamble is no easy task.  With each year’s event, they’re basically overwritten on the web.  It’s also likely that the results from 2016 are no longer relevant. This year also marks the first time this event has been held on a Saturday which theoretically features higher-quality racing compared to its usual Sunday placement.  The contest game has changed, for better or worse.  The ability for players to enter using ADWs and not be forced to make the trip to Lexington has increased some contest sizes and also made the results significantly more volatile.  Instead of referencing past Grade 1 Gamble results, I’ve looked to some of the recent XpressBet contests that feature a similar buy-in along with a prize pool that is somewhat comparable (not so top-heavy).

Projecting the necessary score to win is difficult but likely somewhere in the range of 10-20X the starting bankroll of $2,000.  My betting philosophy and overall approach will make this difficult to achieve.  I’m okay with that as winning the contest isn’t my main objective – Many will argue this mindset puts me at a huge disadvantage and I’ll vehemently disagree.  I’d also bet I’m not alone here.  Don’t get me wrong, if I’m in a position, I’ll take a shot at winning but not at the expense of my main objective.

Again, my goal is to finish in the Top 6, and based on some of the recent contest results, I believe I’ll need to end up with somewhere between 4-5X the starting bankroll.  So I’ll be trying to finish with $8,000-$10,000 on Saturday.  It’s still a tall order, and something that likely could have won the contest just a few years ago, but it’s much more manageable compared to 10-20X.

Weather aside, my first glance at the card makes me think someone will likely jump out to a big, early lead.  I’m actually hoping for this as I think it will make others more likely to alter their game plan and chase, while I’ll be undeterred in my overall strategy.  The Grade 1 Jenny Wiley Stakes has a small field and the finale, although a MSW, looks to have a couple of very formidable entrants.  Thus, if the last two races appear formful on paper, folks will be taking their swings earlier in the card.  Someone will connect and they’ll be the target.

As for me, I think the Grade 3 Stonestreet Lexington Stakes is a fantastic race.  If I make any noise in this contest, it’ll be after the conclusion of this derby prep.  I’ll hope to get most of the minimums (5 bets of $400) out of the way relatively early while building up some bankroll to take a swing in this race.  I have my key horse in mind, without needing to handicap, and I expect this will be my prime play of the day – It’s not Bezos, though that last line would have been a lot more clever if it was (get it? Prime).

I’m going to be optimistic and assume I’ll have a winning opinion in the Lexington.  With two races to go, I’ll be flexible as to how I approach things from there.  A lot will depend on the leaderboard and where I’m at relative to my goal.  Ideally, I’d have something over $8,000 going into the Grade 1 Jenny Wiley.  Roughly speaking, I’d use the amount over the minimum target (4X – $8,000) as bankroll to try and land somewhere north of the 5X target in the last two races.

Hopefully, you’ve found this helpful, whether you’re playing or not.  If you’re on the fence about playing in this contest, it’s one I’d strongly suggest.  You can register and find additional details on the Keeneland Site.

Best of luck to those who are playing. Though I hope only a few of you have more success than me!

Leave a Reply

Further reading