Humphrey and Banwell had purchased Improbable's dam, Rare Event, for $400,000 as a yearling in 2010, a reflection of her excellent pedigree as a daughter of Belmont Stakes and Breeders' Cup Classic winner A.P.
He likely suffered oxygen deprivation during the delivery, resulting in a failure to thrive in the days after birth (sometimes called dummy foal syndrome).
[2] Improbable was sold as a weanling in 2016 for $110,000 to Taylor Made Agency, which resold him as a yearling in 2017 for $200,000 to WinStar Farm's Maverick Racing and China Horse Club.
When he was later put into training with Bob Baffert in 2018, he was placed in the stall of the recently retired Triple Crown winner Justify,[2] who looked very similar to Improbable as they were both big powerful chestnut colts with a white blaze.
Going off as the 5-2 favorite, Improbable stalked the early pace, then took the lead on the far turn and easily held off a late run from King Jack to win by 2+3⁄4 lengths.
The Oaklawn Mile, an ungraded stakes race, attracted a strong field of older horses due to the COVID-19 related closures of many racetracks in the spring.
Improbable went off as the second betting choice behind Tom's d'Etat, who was making his first start of the year after finishing his 2019 campaign with wins in the Fayette Stakes and Clark Handicap.
He briefly took the lead at the head of the stretch but was no match for Tom's d'Etat, who pulled away late to win by three-quarters of a length.
Despite acting up again in the starting gate, Improbable broke well and pressed the early pace set by long shot Mr. Buff.
Maximum Security became another member of the Baffert stable after his original trainer was indicted in March 2020 for doping-related charges.
The new running style seemed to work and Improbable opened up a lead and was geared down at the wire to win impressively by 4+1⁄2 lengths over Maximum Security in a final time of 1:49.01.
Improbable made a huge rally at the leader, Kentucky Derby and Haskell Invitational winner Authentic, but couldn't catch him, finishing second.