Siege of Boston ends long drought in Saturday feature

LAUREL, MD— Jockey Madeline Rowland was all smiles at Laurel Park after she guided Winning Trip to a prompt-and-pounce victory in Saturday’s second race, a $25,000 starter allowance for 3-year-olds and upward.

Rowland, 22, reached a special milestone when Winning Trip became the 100th winner of her career.

“I’ve been wanting it for a while, but I haven’t really been stressing about it because it would come,” Rowland said after conferring with Winning Trip’s trainer, Michael Gorham.

“He’s just been great,” Rowland said about Gorham. “When you’re going through the motions of this sport, you really want people like Mike to come to you, to give you a shot, to believe in you because you can be low. But if there’s someone to put you on those horses, it brings you right back up.”

Rowland and Gorham’s relationship has come full circle. Rowland’s first career ride came aboard the Gorham-trained Joyce G. on Oct. 23, 2021.

“I’ve known Maddie for a while,” Gorham said. “She’s a good rider. She does everything right. She knows where to position them, and she’s a pretty smart rider. Obviously, the horses run for her. She helps us out good in the morning. She breezes a lot of horses over the summer. We’ve been lucky. Our percentage has to be pretty good this year.”

The trainer’s math is correct. After Winning Trip’s victory, the Rowland-Gorham combination boasts a 2025 record of 8 wins from 26 starts.

Rowland comes from a racing family. Her late father, steeplechase trainer Paul Rowland, saddled several quality runners, including multiple stakes-winner Preemptive Strike.

Her first win occurred at Tampa Bay Downs on Dec. 10, 2021. She enjoyed a career year as an apprentice in 2022, winning 56 races for $1,364,480.

Rowland has been open about some of her emotional struggles over the past few years.

“A lot of jockeys go through the ups and downs, even trainers,” she said. “You have it be your identity. I took being a jockey as my only identity. I took it so serious, which it is serious, but it’s also not that serious. What I had to learn was to enjoy each trip, each journey, instead of worrying about how it’s going to go. Because you worry a lot about how it’s going to go, how you’re going to perform, how you’re going to pick up a slow horse and make it fast. You think about that kind of stuff, but then you get an opportunity like Mike’s been giving me, and it makes you look back and realize that God’s going to send you someone to help you out.”

*Siege of Boston ends long drought in Saturday feature

It was a long time between drinks for Siege of Boston, but the multiple Grade 3-placed 6-year-old finally got back to the winner’s circle in the featured fourth race, a $56,000 allowance at 1 1/16 miles over the Fort Marcy Turf Course.

Ridden by Jorge Ruiz for trainer Jimmy Toner, Siege of Boston settled near the back while Love Me Not cleared off to set a solid opening quarter in 23.87 seconds. Jack’s Legend advanced outside the pacesetter through a half-mile in 47.30 seconds, and that move might have set things up for the late runners.

Love Me Not and Jack’s Legend were all in after six furlongs in 1:11.41, and they felt the effects of their skirmish.

Ruiz angled Siege of Boston into the clear, and they stormed home to outfinish fellow closer McCullough by 1 ¾ lengths. Favored Forever Souper was third, a nose behind the runner-up. Love Me Not, Jack’s Legend, and Hittheroadjak completed the order of finish.

Siege of Boston raced the distance in 1:40.12 over the firm course and paid $7.40 as the second choice in the wagering.

“He’s a nice horse,” Ruiz said. “When you ask him, he picks his spot. Jimmy told me to break good, relax, and make one run. Easy.”

Siege of Boston is owned by Joseph Allen LLC and was bred by Allen in partnership with White Birch Farm. By Claiborne Farm stallion War Front, he is out of multiple French Group 2 winner Peintre Rare, a half-sister to European Horse of the Year Peintre Celebre.

After taking a second-level allowance at Laurel on June 18, 2023, Siege of Boston suffered through 15 consecutive losses. Although winless during that span, he ran well in several nice races, finishing third in the Grade 3 River City Stakes at Churchill Downs in 2023, third in the Grade 3 Tampa Bay Stakes in his 2024 debut, and second in Gulfstream’s Grade 3 Canadian Turf one month later.

Siege of Boston has won 4 times from 26 starts, earning $566,571.

Around the track:

Gorham gave updates on two of his stable stars. Multiple stakes-winner Pay Billy, unraced since finishing seventh in Pimlico’s Grade 1 Preakness Stakes, is possible for the $100,000 City of Laurel Stakes at seven furlongs on Nov. 29. Multiple stakes-placed Omaha Omaha is likely for a second-level allowance routing on dirt. “Both of them were turned out, they both grew up a little, and they’re both doing pretty good,” Gorham said…Laurel Park-based Next Girl successfully shipped to Churchill Downs on Saturday for the $100,000 Claiming Crown Glass Slipper. Robbie Bailes trains the Maryland-bred daughter of Country Life Farm stallion Divining Rod…Live racing resumes Sunday with a 10-race program. The first post time is 12:00 p.m. ET, and there are two “Value Pick 5” wagers, each with a low 12% takeout rate…The FREE “Laurel Park Handicapping Guide” is available every racing day. See picks, a full-card analysis, trainer stats, trip notes, horses to watch, track bias information, and lots more from The Maryland Jockey Club’s team of analysts. Sunday’s Guide is available here: click here to view…Reserve your spot for our weekly “Bubbly Brunch Sundays.” Kick back with friends over delicious brunch favorites and bottomless mimosas in our vibrant Stone Bar Restaurant and Bar. Sunday Brunch begins at 11:00 am ET…Join us at Laurel Park on Thanksgiving Day for an all-inclusive buffet, and receive a FREE apple or pumpkin pie with the purchase of a racing program. Click here to learn more. …Never miss a second of the action with the Laurel Park YouTube channel. Click here to catch full pan and head-on replays.