However, Moquett soon noticed that "he was neither a Mel or pleasant", so renamed the horse after a high school basketball teammate known for his athleticism.

[6] Whitmore was trained by Moquett, who later sold shares of the horse to Robert LaPenta and Head of Plains Partners (Sol Kumin).

On November 6 he made his first start in a six-furlong Maiden Special Weight at Churchill Downs, which he won by 7+1⁄4 lengths despite veering out in the stretch.

[7] Stepped up in distance for the $1,000,000 Delta Downs Jackpot Stakes, he was in close contention for the first three-quarters but had nothing left in the stretch and finished fifth.

[9] Whitmore began his four-year-old campaign on January 15 by winning a six furlong allowance race at Oaklawn Park.

"[12] On May 20, Whitmore extended his winning streak to five by taking the Maryland Sprint Stakes at Pimlico Race Course, beating Grade 1 winner A.P.

As soon as I asked him, he started running," said jockey Ricardo Santana Jr.[13] The winning streak was broken in the True North Handicap at Belmont Park on June 9, when Whitmore raced wide around the final turn and finished third behind Roy H. "I've always been happy when he gets a position on the inside of horses.

[16] Whitmore returned in the Phoenix Stakes at Keeneland on October 6 with a late run, prevailing by a neck in a photo finish.

In the Forego Stakes at Saratoga Race Course on August 25, Whitmore faced an excellent field that was led by City of Light and Limousine Liberal.

Whitmore rated behind the early pace on the rail while City of Light was forced to go wide after breaking poorly.

Whitmore stalked in third place, then gradually closed ground down the stretch, coming up a head short at the wire.

[21] Whitmore faced another top-notch field in the 2015 Breeders' Cup Sprint, held on November 3 at Churchill Downs.

He broke slowly and settled in last place along the rail behind a very fast pace of 21:35 seconds for the first quarter-mile set by Promises Fulfilled.

Roy H bobbled at the start after bumping into his stall, then made up ground while racing four wide and took the lead after half a mile completed in :44.21.

[31] Unlike many other racetracks, Oaklawn Park remained open during the early phase of the COVID-19 pandemic, though they did limit attendance to essential personnel.

Whitmore raced in his fourth Count Fleet Sprint Handicap, this year held on April 18.

The race had attracted a very strong field with several horses shipping in from other states, including recent stakes winner Flagstaff and the highly regarded Hidden Scroll.

The race scratched down to just four horses, with the odds-on favorite Volatile going gate-to-wire to win by 1+1⁄4 lengths over Whitmore, who was unable to close much ground after a relatively slow early pace.

Racing just off the rail in seventh during the early running, he swung wide near the head of the stretch and closed steadily but came up short behind Diamond Oops.

[37] Moquett attributed the gelding's longevity to his come-from-behind style, which meant the horse was less tired in the stretch where most injuries occur.

"[38] The Breeders' Cup Sprint, held on November 7 at Keeneland, attracted a very competitive field, lacking the clear standout of the previous years that were headlined by Roy H and Mitole, both of whom were later named champion sprinter.

Moquett later said he was tempted to tell jockey Irad Ortiz Jr. to go for the early lead instead of following Whitmore's normal running style.

The jockey compromised by taking Whitmore well back in the early running and cutting over to the rail for a ground-saving trip.

Longshot Jasper Prince took the early lead, pressed by Empire of Gold, and ran the first quarter-mile in :21.64 and the half in :44.66.

I'm proud for everyone out there that's thinking when you run last in the Kentucky Derby, kick them out – do right by the horse, come back, and you have a shot to reach other dreams.

[43] The Blood-Horse magazine called it one of the most popular wins of the 2020 Breeders' Cup, a nod to Whitmore's strong following among racing fans.

In sixth place after half a mile, Whitmore made his move as they turned into the stretch, taking the lead with a furlong remaining.

[46] Whitmore's next start was the Count Fleet Sprint Handicap on April 10, where he faced C Z Rocket again, hoping to turn the tables on his rival and win this race for the fourth time.

[47] He then raced in the Churchill Downs Stakes on May 1, where he finished third behind the consistent Californian sprinter Flagstaff and longshot Lexitonian.

He rated in mid-pack and started to close ground around the turn, but was bumped and faced traffic problems in the stretch.