When the most exciting two minutes in sports get underway in less than two weeks, the focus will rightly be on the horses and jockeys making the 1 ¼ mile run for a spot in history. But the path to Derby Day and to the elusive winner’s circle at Churchill Downs is paved with a series of important decisions and transactions that happen long before the first Saturday in May. There’s a game of careful strategy to be played when it comes to horse racing, and increasingly that game runs through an elite group of trainers whose resumes redefine success in the sport.The big yearling sales in Lexington and Saratoga are akin to the NFL combine or any major gathering of prospects in a top sport.
The big-bucks owner connects with a bloodstock agent who steers your way to a top prospect who might even get to the Kentucky Derby. When you win that horse at auction, you may have spent into the millions. It is an investment, to be sure, and it must be nurtured by the services of only the best horse trainers.
In the present day, it’s not just individual big-bucks owners who are buying these horses, but partnerships or conglomerates of moneyed people. Cost is no issue.That rise of partnerships and conglomerates has led to a generation of “super-trainers,” as some call them. These trainers frequently have as many as 200 horses running in their name, and they are often based at several different racetracks or training centers.These trainers do not hang a shingle outside their barn that says “super-trainer”.
Their statistics speak for themselves. I’ve singled out six trainers for an exploration of exactly how important they are for these owners and the sport. Here’s a breakdown by average annual purse earnings from 2025 back to 2020, and where they ranked annually among North American trainers in those years.BRAD COX – Average annual purse earnings: $27.5 million National rankings: 1, 3, 1, 4, 1, 2CHAD BROWN – Average annual purse earnings: $25.1 million National rankings: 3, 1, 4, 1, 3, 4STEVE ASMUSSEN - Average annual purse earnings: $26.3 million National rankings: 2, 2, 2, 3, 2, 1TODD PLETCHER - Average annual purse earnings: $21.5 million National rankings: 5, 4, 3, 2, 4, 7BILL MOTT - Average annual purse earnings: $14.2 million National rankings: 6, 11, 5, 5, 8, 8MARK CASSE – Average annual purse earnings: 16.5 million National rankings: 4, 5, 6, 7, 6, 6Of this grouping, the only trainer who did not place in the top seven for all six years was Bill Mott.
His slightly lower numbers are explained by the fact that he starts less horses, but trains for absolutely the wealthiest and most elite owners. In the category of earnings per start, he ranks right with Cox, Brown, and Pletcher.But how have these trainers actually done in the Kentucky Derby? It’s an odd set of results, to be sure.BRAD COX Of 12 starters, his only winner was Mandaloun, who actually finished second in the race.
The horse who was first was Medina Spirit, who several months after the race was disqualified for a drug violation.TODD PLETCHER The all-time Kentucky Derby record holder with 65 starters. In 2013 he had five horses in the race, and four times he had four horses. It can reasonably be assumed that many of these horses were entered because the owners wanted to have a horse in America’s biggest race, although they might be overmatched.
From his record number of starters, Pletcher won in 2010 with Super Saver and 2017 with Always Dreaming. He is 2-for-65.Todd PletcherPat McDonogh / Courier Journal via Imagn Content Services, LLCBILL MOTT The youngest trainer ever inducted in the Racing Hall of Fame (at age 45 in 1998), he has also won five Eclipse Awards as the top trainer in the country. His first Derby win came in the unusual case of the disqualification of Maximum Security, who crossed the line first in 2019.
On his way, however, he interfered with other horses. Mott’s Country House came up on the outside to finish second. Although he was not interfered with, he was put up for the win.
His other Derby win was in the more traditional fashion last year with Sovereignty, who went on to become Horse of the Year.CHAD BROWN No wins from nine Derby starters, although he has been second twice (Good Magic in 2018 and Sierra Leone in 2024). Brown is a relatively young trainer at the top of his game, and many more opportunities at the big prize are in his future.STEVE ASMUSSEN He has won over 11,000 races, more than any trainer in North American history. The Kentucky Derby, however, is another issue.
Mr. Asmussen has the biggest Derby 0-fer among active trainers. He is 0-for-28, with three seconds and two thirds. Perhaps his toughest beat was in 2022, when his Epicenter prevailed in a stretch duel with Zandon, but both were surprised by 80-1 Rich Strike coming up the rail to win the race. For all that he has given to the game, I hope a Kentucky Derby is in Steve Asmussen’s future.MARK CASSE A member of the Canadian and American Halls of Fame, Mark Casse has had