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