Kentucky Derby Winners Ranked 2000-2025 - PTF/Duke Matties

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 DrysdaleMonarchos (2001) | J: Jorge Chavez | T: John Ward Jr.War Emblem (2002) | J: Victor Espinoza | T: Bob BaffertFunny Cide (2003) | J: Jose Santos | T: Barclay TaggSmarty Jones (2004) | J: Stewart Elliott | T: John ServisGiacomo (2005) | J: Mike Smith | T: John ShirreffsBarbaro (2006) | J: Edgar Prado | T: Michael MatzStreet Sense (2007) | J: Calvin Borel | T: Carl NafzgerBig 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 PletcherAnimal Kingdom (2011) | J: John Velazquez | T: Graham MotionI'll Have Another (2012) | J: Mario Gutierrez | T: Doug O'NeillOrb (2013) | J: Joel Rosario | T: Shug McGaugheyCalifornia Chrome (2014) | J: Victor Espinoza | T: Art ShermanAmerican Pharoah (2015) | J: Victor Espinoza | T: Bob BaffertNyquist (2016) | J: Mario Gutierrez | T: Doug O'NeillAlways Dreaming (2017) | J: John Velazquez | T: Todd PletcherJustify (2018) | J: Mike Smith | T: Bob BaffertCountry House (2019) | J: Flavien Prat | T: Bill MottAuthentic (2020) | J: John Velazquez | T: Bob BaffertMandaloun (2021 — history's winner) | J: Florent Geroux | T: Brad CoxRich Strike (2022) | J: Sonny Leon | T: Eric ReedMage (2023) | J: Javier Castellano | T: Gustavo DelgadoMystik Dan (2024) | J: Brian Hernandez Jr. | T: Kenny McPeekSovereignty (2025) | J: Junior Alvarado | T: Bill Mott PHOTO CREDITSAmerican Pharoah — Eclipse SportswireAnimal Kingdom — Eclipse SportswireAlways Dreaming — Coady PhotographyAuthentic — Coady Photography / Churchill DownsBarbaro — EquiPhotoBig Brown — Coady Photography / Churchill DownsCalifornia Chrome — Reed Palmer PhotographyCountry House — Coady Photography / Churchill DownsFunny Cide — Coglianese PhotosFusaichi Pegasus — Coady Photography / Churchill DownsGiacomo — Churchill Downs / KD TwitterI'll Have Another — Eclipse SportswireJustify — Coady Photography / Churchill DownsMage — Coady Photography / Churchill DownsMandaloun — Coady PhotographyMine That Bird — Eclipse SportswireMonarchos — Coady Photography / Churchill DownsMystik Dan — Coady Photography / Churchill DownsNyquist — Eclipse SportswireOrb — Eclipse SportswireRich Strike — Coady Photography / Churchill DownsSmarty Jones — EquiPhotoSovereignty — Coady Photography / Churchill DownsStreet Sense — Coady Photography / Churchill DownsSuper Saver — Eclipse SportswireWar Emblem — Coady Photography / Churchill Downs