'Finally' Healthy: 2018 Champion Apprentice Weston Hamilton Returns To Maryland

Six years after gaining national attention as an Eclipse Award-winning apprentice, jockey Weston Hamilton is back in Maryland to begin the latest chapter of his riding career.

Hamilton, 25, made his return on the second weekend of Laurel Park’s 15-day spring meet, finishing second aboard Heads Or Tails April 13, his first race since Sept. 16, 2023 at Remington Park and first time riding in Maryland since Dec. 13, 2020, also at Laurel.

“It felt like I never left,” he said. “Everyone’s happy to see me. Me and my agent, Joe Rocco, we’re out there getting at it every morning and going track to track. We’re ready to get going here. It’s going to come together. We’ve just got to keep working hard, that’s the main thing, and keep trusting in the Lord.”

Hamilton is the youngest son of former jockey Steve ‘Cowboy’ Hamilton, a popular and successful rider in Maryland over three separate stints, the last ending in 2018 due to a back injury which ultimately ended his career. Wes Hamilton lived in Maryland through fifth grade before the family moved back to their father’s native Oklahoma.

“It was a good trip being back home in Oklahoma, but both places are home to me,” Hamilton said. “I was born in Maryland and grew up in Oklahoma as a teenager. I love both places.”

Hamilton turned down a scholarship offer to play collegiate lacrosse in order to chase his dream, making his professional debut Dec. 2, 2017 at Laurel. He picked up his first two winners on the same program there nine days later, appropriately breaking his maiden with I Just Wanna Win for trainer Pat McGill.

During his 2018 championship season Hamilton led all apprentices with 118 wins and was second with $3.4 million in purse earnings, going 120-for-920 overall with a $3.5 million bankroll and ranking second in Maryland with 106 wins at Laurel and historic Pimlico Race Course. Including the final month of 2017, he won 126 races during his apprenticeship.

Hamilton won 31 races in Maryland during the pandemic-shortened 2020 season and rode at Remington in Oklahoma and Sam Houston and Lone Star Park in Texas from 2021 to 2023, missing time due to injury. He returned to Maryland with 331 wins and $10.5 million in purse earnings from 3,228 mounts.

“My stirrup leather broke when I came out of the gate one time and landed on myself the wrong way and had to have some surgeries there. I had a horse flip on me in the gate. I was out like three times for six months at a time,” Hamilton said. “I took some time off and was out for about 10-11 months and after that I said, ‘It’s time now.’”

Hamilton enters Friday’s card at Laurel with one second and one third from his first 10 mounts back, riding for trainers Robert Leaf Jr., Hugh McMahon, Corby Caiazzo, Phil Capuano, Derrick Parram, Anthony Lucas, Timothy Vick and Hassan Elamri. He is named in Friday’s opener aboard Amanda Rawlings-trained Stormy Fire, and has mounts in three races Saturday and four races on Sunday’s closing day.

“I really just missed it. I love it here,” Hamilton said. “I’ve lived here for half my life. I had some surgeries and was out for a while, and I didn’t know if I’d ever be able to ride again. I finally got healthy and went back to galloping and working some horses, and I felt better than before, so I was ready to get back to it.”

Hamilton ranked in top 10 in wins and purses earned at Remington in 2021 (26, $712,492) and 2022 (40, $1.1 million) and Sam Houston in 2023 (15, $486,403). He was 11^th with 18 wins and $468,143 in purse earnings at Lone Star in 2023.

Among Hamilton’s stakes wins are the 2019 Nellie Morse (Timeless Curls) and 2020 What a Summer (Victim of Love) at Laurel, 2022 Groovy (Lucky’s Special) at Sam Houston and 2022 Will Rogers (Beckett’s Luckyday) at Will Rogers Downs. Hamilton and Victim of Love also ran second in the 2020 Barbara Fritchie (G2).

“I had a good run at it in Texas and Oklahoma,” he said. “I just wanted to come back here. I know a lot of people here. I’ve done good here and my dad’s always done good here. I just missed it. There’s good racing around here. There’s tons of tracks to go to and I’m hungry to be back at it.”