Todd Pletcher, a six-time Eclipse Award winner, topped the earnings list with US$22.4 million but had failed to win a Triple Crown or Breeders' Cup race. Brown believed he was destined to take home his first Eclipse Award as the outstanding trainer.

Yet as disappointed as Brown felt five years ago, he can now look back and laugh about it. Not only did Brown win his first Eclipse Award as the top trainer in 2016, he has taken home the prize in each year since.

His latest award came when he was announced as the 2019 recipient of the industry's top prize for a trainer, putting him in the company of Pletcher, Laz Barrera, and his beloved mentor Bobby Frankel as the fourth trainer to win four straight Eclipse Awards.

Brown again won three Breeders' Cup races in 2019, but putting him over the top with voters was training Horse of the Year Bricks and Mortar and becoming the first trainer to top $30 million in annual North American earnings with $31,112,144 and 20 grade 1 win among his 222 victories.