LOUISVILLE, Ky. -- Gayle Benson didn't get to see the colt named in honor of her husband almost win the Louisiana Derby.
It was Saturday, March 24, 2018, and Benson was a significant absence at the Fair Grounds Race Course that day in her hometown of New Orleans. It was a week tinged with sadness. Her husband, Tom Benson, the late owner of the NFL's Saints and NBA's Pelicans, had been laid to rest the previous day.
Twenty-four hours later, Lone Sailor thrust his head in front down the long Fair Grounds homestretch, trying valiantly to hold off Noble Indy. Lone Sailor couldn't, just missing a victory, but it was enough to get him into the Kentucky Derby starting gate.
Lone Sailor's trainer, Tom Amoss, a lifelong New Orleanian, had wanted to win the race his entire life. Winning with Lone Sailor, who was named in honor of a Navy Memorial Foundation service award Tom Benson received in 2007, would've meant the world to Amoss.
But in the quiet hours after the celebration had died down, he looked down at his phone and saw a text from Gayle Benson that made him decide second place sometimes could feel just like a win.
"I'll keep the text she sent me after the Louisiana Derby for the rest of my life. It meant a lot to me to get a text that night," Amoss said. "Obviously, she wasn't going to be at the race. It was the day after the funeral, but it meant a lot to me and it made me feel in my own little way like I had given something back to a family that had really, not only me, but the city of New Orleans, had given so much through the Saints. ...
"They're the Saints! I mean, I grew up with them, my family grew up with them, I used to go to the games with my brothers and my dad. For any New Orleanian, they were a part of our lives."
It has become clear that horse racing has suddenly and quickly become a major part of Gayle Benson's life.
Tom and Gayle Benson started GMB Racing in 2014 after enjoying trips to New York's Saratoga Race Course together. It was Gayle who nudged her husband back into the business after decades of inactivity.
Tom had sold off all his horse racing interests years earlier after his son, Robert "Bob" Benson, died of cancer in 1986. Bob had run the operation, which saw moderate success with stakes winner Si Cima in the late 1970s and early 1980s. When he died, Tom lost all interest in keeping up that part of his life, but Gayle made him remember how much fun he used to have around the track.
The Bensons have had an unprecedented amount of success since then, sending Mo Tom and Tom's Ready, two horses from their first crop of purchases, to the Kentucky Derby in 2016.
It's an astonishing amount of success for a small operation that bought its first horses at bargain prices. Just how hard is it to get into the Derby? Only 20 horses will make it to the gate on Saturday out of the 21,500 registered thoroughbreds born in 2015.
Even Colonel Edward R. Bradley, who started a record 28 horses in the Derby and won four times, took 20 years to get his first starter in the gate. By Golly, who was one of just 1,680 registered thoroughbred foals that year -- 1917 -- finished seventh.
"It's a race that can't be bought," Amoss said. "And many people have tried to buy it in the past."
What hasn't become clear is which operation ranks highest in Gayle Benson's life in the weeks since she was suddenly tasked with running two professional sports teams, in addition to a thoroughbred racing and breeding operation. Ownership transferred to her in an unprecedented time of success for the Benson sports teams.
The Saints had just come off their first playoff appearance since 2013. The Pelicans not made it to only the postseason, but they swept the Portland Trail Blazers in the first round.
As for the riding side, the operation has transformed from making a single start in 2014 to a full-fledged racing operation, in addition to a 273-acre breeding farm in Kentucky.
Somehow, Benson has committed to making it work, crisscrossing the country to watch the Pelicans continue in the postseason against the Golden State Warriors in California and New Orleans, all while keeping an eye on the horses in Kentucky. After the Pelicans' home victory over the Warriors on Friday, she was scheduled to take a plane to Louisville.
It was clear she wasn't going to miss seeing Lone Sailor this time around. Shortly after the Louisiana Derby, she placed a personal call to NBA commissioner Adam Silver to request the Pelicans play on any day but the first Saturday in May.
An NBA source confirmed that the call occurred and they would've been willing to listen to the request, but they didn't need to because the schedule already had the Pelicans playing on a Friday instead.
"I think that tells you where horse racing fits in her world. It's important," Amoss said.
Lone Sailor was a 29-1 long shot on Saturday morning, and it will be a monumental task for him to win the Kentucky Derby. But with all that has happened this year, Amoss said he wondered if it was meant to be.
"I think that fate has a lot to do with which horses make it there," he said. "As in any sport, injuries come into play, not just talent. ... And I think reflecting on all the things that made that specific horse make it all the way to the Kentucky Derby, you just kind of look at it and say, part of it has to be fate."
Although her husband is gone, it's clear Benson isn't planning on giving up the racing operation anytime soon.
"This isn't the closing chapter," Amoss said. "This is the beginning of the story for the Bensons and horse racing."