During his summers off from junior and senior high school, he went to California, where he worked as a hot walker for Henry Moreno at Hollywood Park and Del Mar Racetracks.

He graduated from James Madison High School in San Antonio, Texas[2] in 1985 and began college at the University of Arizona in their Race Track Industry Program in the fall of that year.

He spent the following summer with another legendary Hall of Fame trainer, Charlie Whittingham, working as a groom at Hollywood Park.

Pletcher was Lukas's East Coast Assistant until fall of 1995[3] where he helped develop horses such as Thunder Gulch, Harlan, Serena's Song, A Wild Ride, and Flanders.

[4] Pletcher broke his own single-season earnings record on October 7, 2006, when Fleet Indian captured the Beldame Stakes at Belmont Park.

Pletcher's season included a win with Bluegrass Cat in the $1,000,000 Haskell Invitational at Monmouth Park following the colt's second-place finishes in the Kentucky Derby and Belmont Stakes.

[6] After missing the winner's circle with 24 previous entries, Pletcher won his first Kentucky Derby on May 1, 2010 with Super Saver,[7] the 8-1 second choice, with jockey Calvin Borel aboard.

He has received several Fourstardave (for Special Achievement at Saratoga Race Course) and Woody Stephens (for outstanding trainer) Awards from the New York Turf Writers Association.