Toledo, a 27-year-old native of Puerto Rico, has won nearly 1,230 races but picked up his first win at Gulfstream, where he was riding for the first time since March 23, 2019, when he was fourth on In the Loop in the Hutcheson (G3). He signed autographs and posed for pictures with fans outside the winner’s circle after the race.

“It feels like we’re in Hollywood,” Toledo said. “It feels great. To win my first race at Gulfstream, and in a stake, and during the Championship Meet it’s really special.”

ProRacing Stable, Al Bianchi Racing, Corms Racing Stable and On The Rise Again Stable’s Headline Hunter ($6.20) finished up in 57.51 seconds over the all-weather Tapeta after the race was rained off the grass, giving trainer Jose D’Angelo his first U.S. stakes win. He captured the 2020 Claiming Crown Jewel with Jesus’ Team, seven months after the son of Tapiture ran third at odds of 40-1 in the Preakness Stakes (G1) with Toledo aboard.

“Jevian rode for me at the Preakness. He said, ‘Every horse you put me on I [will] always go,” D’Angelo said. “I called him [to ride Headline Hunter] and he said, ‘I can do that.’ I’m glad because we are a team and we did the job.”

Claimed for $35,000 out of a win over the Gulfstream Tapeta last November, Headline Hunter settled in second pressing multiple stakes winner and 8-5 favorite Miss Auramet through a quarter-mile in 22.50 seconds under a snug hold from Toledo. Headline Hunter moved up to even terms rounding the far turn and began to edge clear once straightened for home, going a half-mile in 45.45 seconds.

“Everybody that basically went to the front today didn’t win,” Toledo said. “I got a good break and I put her right there in a good spot. When I asked her in the stretch, she just took off. She’s a nice filly. She looks like she’s getting better and better.”

Miss Auramet held second, a length ahead of fellow multiple stakes winner Miss J McKay, followed by La Libertee and Bernie’s Mistress. Naughty Shirley was pulled up on the far turn and vanned off. Tobys Heart and A G Indy were scratched.

It was the fourth win from five tries on Tapeta for Headline Hunter, the last three of them coming at Gulfstream including a five-furlong allowance Feb. 9 in the prep for her stakes debut. Only three of her rivals had tried the all-weather surface before, with La Libertee going 1-for-4 over it.

“She was the only won that been winning on that kind of course before and she ran huge today,” Toledo said. “She carried me all the way.”

Represented by agent Marty Leonard, Toledo leads the current Laurel Park winter meet with 32 victories, and is second with $1.07 million in purse earnings. He owns seven career meet titles in Maryland, all at Laurel, the most recent coming in the 2021 calendar year-ending fall stand.

“It’s been a great winter. My agent does a really good job and I have a lot of support from the owners and trainers and they really help me,” Toledo said. “Like I always say, this is horse racing and if you have the right horse you’re going to win races. Thank God we work together and I’ve been getting the opportunities and we try to do our best to get it done every time.”

In addition to last year, Toledo won Maryland’s overall riding championship in 2015 and 2017. He was already scheduled to be at Gulfstream for the Captiva Island, picking up five other mounts, when Laurel had Saturday’s live program canceled due to a severe winter storm.

“I picked up some mounts and it really worked out pretty good. It’s really nice to be here. We ended up not having anything [at Laurel] so it’s pretty good that I could still be riding today,” Toledo said. “I came in last night. My flight was cancelled tonight and they moved it to Monday so I have to see if I can get another flight for tomorrow because I ride [at Laurel] tomorrow. Hopefully, I can find a flight to get back.”

Toledo is named in five races Sunday at Laurel including multiple stakes winner Dontletsweetfoolya in Race 8, an open allowance for older females sprinting 5 ½ furlongs that also attracted stakes winners Kaylasaurus and Princess Kokachin.