In this special presentation from In The Money Media, Duke Matties — the man behind Duke’s Picks and one of the sharpest handicapping minds in the game — joins PTF as he takes on one of the great debates in modern thoroughbred racing: how do you rank the Kentucky Derby winners of the 21st century?
From dominant Triple Crown champions to miraculous longshots that had no business winning, every winner from Fusaichi Pegasus in 2000 through Sovereignty in 2025 goes under the microscope. Duke builds his tier list live — Elite, A, B, C, and the infamous “Somehow” tier — and Pete holds him accountable every step of the way.
Where does American Pharoah land? Is Justify underrated or overrated? And which winners are going straight to Somehow the moment their card hits the board?
Find out.
EVERY DERBY WINNER RANKED (2000–2025)
Fusaichi Pegasus (2000) | J: Kent Desormeaux | T: Neil Drysdale
Monarchos (2001) | J: Jorge Chavez | T: John Ward Jr.
War Emblem (2002) | J: Victor Espinoza | T: Bob Baffert
Funny Cide (2003) | J: Jose Santos | T: Barclay Tagg
Smarty Jones (2004) | J: Stewart Elliott | T: John Servis
Giacomo (2005) | J: Mike Smith | T: John Shirreffs
Barbaro (2006) | J: Edgar Prado | T: Michael Matz
Street Sense (2007) | J: Calvin Borel | T: Carl Nafzger
Big Brown (2008) | J: Kent Desormeaux | T: Richard Dutrow Jr.
Mine That Bird (2009) | J: Calvin Borel | T: Bennie Woolley Jr.
Super Saver (2010) | J: Calvin Borel | T: Todd Pletcher
Animal Kingdom (2011) | J: John Velazquez | T: Graham Motion
I’ll Have Another (2012) | J: Mario Gutierrez | T: Doug O’Neill
Orb (2013) | J: Joel Rosario | T: Shug McGaughey
California Chrome (2014) | J: Victor Espinoza | T: Art Sherman
American Pharoah (2015) | J: Victor Espinoza | T: Bob Baffert
Nyquist (2016) | J: Mario Gutierrez | T: Doug O’Neill
Always Dreaming (2017) | J: John Velazquez | T: Todd Pletcher
Justify (2018) | J: Mike Smith | T: Bob Baffert
Country House (2019) | J: Flavien Prat | T: Bill Mott
Authentic (2020) | J: John Velazquez | T: Bob Baffert
Mandaloun (2021 — history’s winner) | J: Florent Geroux | T: Brad Cox
Rich Strike (2022) | J: Sonny Leon | T: Eric Reed
Mage (2023) | J: Javier Castellano | T: Gustavo Delgado
Mystik Dan (2024) | J: Brian Hernandez Jr. | T: Kenny McPeek
Sovereignty (2025) | J: Junior Alvarado | T: Bill Mott
PHOTO CREDITS
American Pharoah — Eclipse Sportswire
Animal Kingdom — Eclipse Sportswire
Always Dreaming — Coady Photography
Authentic — Coady Photography / Churchill Downs
Barbaro — EquiPhoto
Big Brown — Coady Photography / Churchill Downs
California Chrome — Reed Palmer Photography
Country House — Coady Photography / Churchill Downs
Funny Cide — Coglianese Photos
Fusaichi Pegasus — Coady Photography / Churchill Downs
Giacomo — Churchill Downs / KD Twitter
I’ll Have Another — Eclipse Sportswire
Justify — Coady Photography / Churchill Downs
Mage — Coady Photography / Churchill Downs
Mandaloun — Coady Photography
Mine That Bird — Eclipse Sportswire
Monarchos — Coady Photography / Churchill Downs
Mystik Dan — Coady Photography / Churchill Downs
Nyquist — Eclipse Sportswire
Orb — Eclipse Sportswire
Rich Strike — Coady Photography / Churchill Downs
Smarty Jones — EquiPhoto
Sovereignty — Coady Photography / Churchill Downs
Street Sense — Coady Photography / Churchill Downs
Super Saver — Eclipse Sportswire
War Emblem — Coady Photography / Churchill Downs
