“#1 – Avery Whisman – Eastern Bay,” the saddle towel read, commemorating the richest horse Whisman rode in his brief career. The duo teamed up to win more than $118,000.

And it was Eastern Bay that brought Cash, his wife, Lola, assistant Jay Libertini, the Whisman family, and others to the winner’s circle. The nine-year-old gelding, evidently as good now as ever, powered to a length-and-a-half victory in the Grade 3 General George to earn the first graded win of his career and zoom past $1 million in earnings.

Cash said he gave the Whismans Eastern Bay’s saddle towel from the General George. The orange-and-black race saddle towel should make a nice contrast with the red-and-white souvenir from the ceremony.

In all, it was part of a day filled with complicated emotions, a day on which riders were happy to win but perhaps made a bit somber as they considered the loss of their onetime competitor, colleague and friend.

“To be honest with you I’m feeling very much purely for Avery. Obviously, this was his favorite horse and his most winning horse and I’m in exactly the same position,” Will Humphrey, who was aboard Eastern Bay, said. “He means the world to me, and it’s like a dream come true and the stars all aligned.” 

“It’s kind of weird, you know,” added jockey Jevian Toledo, who won two stakes on the afternoon. “With what happened, we’re always thinking, we’ve all been in that position. It kind of made you think about everything.”

Toledo, who hit the 1,400-win mark for his career while winning three times today, is, though just 28, now a veteran of the local colony and was Maryland’s leading rider in 2022. The Whisman ceremony took place following the fifth race; minutes later, Toledo won the John B. Campbell Stakes aboard Nimitz Class. He followed that up in the seventh with a win aboard Hybrid Eclipse in the Nellie Morse.

[Story continues below photo]

“We’re here working like, like work that everybody does,” the rider said. “But we gotta get focused back; when one race is over, it’s not coming back.”

Richard Monterrey, too, was feeling the weight of the moment. The 38-year-old journeyman earned the first graded win of his career aboard Swayin to and Fro in the Grade 3 Barbara Fritchie Stakes; the win will more than double his purse earnings to date this year and put him on pace for his best season since 2013, when he rode 43 winners and netted purse earnings of nearly $1.2 million.

“I’ve been there where he was because I struggled with weight,” Monterrey said. “I didn’t get enough [mounts], and when you are in that kind of position, it is difficult… That kind of struggle takes a toll on the body and the mind and all of that.”

Monterrey, a winner of 775 races in a career that began in 2003, struggled so mightily that he finally had had enough. He rode 14 races in 2016 and hung up his tack, thinking it might be for good. But he resumed riding in 2021, had improved results in 2022, including a win in the Maryland Million Turf, and may be en route to bigger things.

“When you are winning, everything is flowers. Everything is good,” he said. But it’s a different world, he said, when wins, even mounts, are hard to come by.

Monterrey said he was fortunate. The time away helped rekindle his love for the sport.

“You try to get opportunities you don’t get, and when that is vanishing, you can start losing the dreams and the passion that you had,” he explained. “I needed to get away from the sport for a little bit, and it took me five years to realize that, you know, this is what I love.”

He’s come back, perhaps, wiser, too. Today he’s on top of the racing world; tomorrow is a new day.

“I was talking to the guys in the jocks’ room, and you have to try to read your fellow riders because you don’t know what they are going through,” he said. “I know some of the guys, I know how they are and I know where they’ve been, because I’ve been there. So what I try to do now is encourage them because I’ve been there and it’s difficult because you get so many negative thoughts in your mind.”

Celebrate the wins, sure; but understand the losses aren’t far away, either.

“This that we did here today is beautiful, this gift to all the racetracks that they’re in an awareness that this sport is beautiful,” Monterrey said. “All of this is beautiful, but these are people that can struggle because they want to make it there to the big stage.”

And maybe, just maybe, there was something the slightest bit mystical in the air.

“I thanked [the Whismans] because maybe Eastern Bay had a little help pushing him down the lane from the powers that be,” Cash said.