"[3] At age eighteen, Romans embarked on a career as a trainer, getting his first winner on February 15, 1987, at Turfway Park with Miss Mindy, who he had purchased for $1,500.

She was the first woman jockey to ride in the Blue Grass Stakes, finishing fourth in 1991.

"[3] Romans' career slowly grew, with 2004 marking his breakout year when he jumped to the #8 ranked trainer by earnings in North America.

[6] In 2005, Roses in May provided Romans with the biggest payday of his career to date when he won the $6 million Dubai World Cup.

[9] Later that year though, he parted ways with owners Kenneth and Sarah Ramsey, for whom he had trained both Roses in May and Kitten's Joy.

[1] The next year, Shackleford gained Romans his first Classic win in the 2011 Preakness Stakes after finishing fourth in the Derby.

Romans said, "It shows that anybody that gets started in the horse business can do this because, Lord knows, 25 years ago nobody thought I'd sit up here and talk about (winning) a classic race.

That year, Romans also trained Dullahan to victories in the Blue Grass Stakes and The Pacific Classic, plus a third-place finish in the Kentucky Derby, Shackleford won the Metropolitan Handicap and Clark Handicap, while Tapitsfly earned Grade I victories in the Just A Game and First Lady Stakes.

[12] Romans is also the trainer of Keen Ice, notable for his August 2015 win over Triple Crown-winner American Pharoah in the Travers Stakes.

Romans confidently predicted the upset, with Keen Ice winning at 16–1 odds.