Jockey Weston Hamilton was only 20 years old when he won the Eclipse Award as the nation’s top apprentice rider and now, four years later he has risen to the summit of the Remington Park standings after two weeks of racing.

It’s early yet, but Hamilton has made it to the winner’s circle seven times in only four days of racing, two ahead of Cristian Torres and three in front of four-time defending riding champion David Cabrera. He is enjoying the view from the top regardless.

“That sounds pretty good, boss,” said Hamilton.

It’s not often in any profession that a kid has a chance to compete against his father, but that’s how Hamilton’s career began. He started riding in December 2017 and got his first win in 2018, the year of his Eclipse Award as an apprentice. His first victory came under unusual circumstances.

“My dad was right next to me in the first win,” said Hamilton, who was riding against his father, Steve “Cowboy” Hamilton in that race. “I was on a horse named I Just Wanna Win. Pat McGill trained that horse. I came from probably 10 lengths back. My dad and I were head-to-head and I had a little more horse than him coming up to the top of the lane and he just yelled. It sounded like he was right in my ear when he yelled, ‘Go on with him, bub!’ I went to riding and I probably could have done a better job, but we got the job done. My dad rode his horse back to the winner’s circle and told them to wait for him (to get into the winner’s circle photo). He jumped off, unsaddled his horse and came and got in the picture. It was awesome. I miss riding with that feller.”

When Hamilton won 120 times as an apprentice that year, he did the majority of his riding in Maryland, fertile ground for new riders who can use a weight allowance. He was the 12th apprentice jockey to be honored nationally from that circuit. He joined the likes of Chris McCarron (1974), Ronnie Franklin (1978), Alberto Delgado (1982), Allen Stacy (1986), Kent Desormeaux (1987), Mike Luzzi (1989), Mark Johnson (1990), Jeremy Rose (2001), Ryan Fogelsonger (2002) and Victor Carasco (2013).

Now Hamilton has joined forces with some of the top owners and trainers at Remington Park, with the help of agent Pete Caparelli, and that has led to early victories. He has ridden winners out of the barns of all-time leading Remington Park owner Danny Caldwell and for owner-trainer C.R. Trout.

Last year was his first full season at Remington Park and he finished 10th in the final standings with 26 wins, 64 victories behind Cabrera’s 90. This year he has had 22 mounts with seven wins, two seconds and two thirds. Torres is at 18-5-4-1 and Cabrera 30-4-6-2.

“To be with Mr. (C.R.) Trout and his assistant Daniel (Ortiz), they work really hard,” said Hamilton. “Mr. Danny Caldwell has given me a lot of opportunities. They have some good horses and he’s been giving me a shot.”

Hamilton was born in Maryland and lived there through fifth grade. In sixth grade, he moved to the Tulsa, Okla., area and went to high school at Kiefer, a suburb of Tulsa. He rode horses a lot, growing up, but moved into sports and played prep lacrosse. Yes, lacrosse in Oklahoma.

“I almost went to college on a lacrosse scholarship, but then I decided I really wanted to ride horses,” he said.

He has been doing it ever since. In his short career, he has ridden 2,695 times, winning 281 races, 302 seconds and 360 thirds for horses’ earnings of $9,056,706. This year, he is 388-33-49-55 for $1,031,659. In his apprentice year, he was 920-120-100-131 for $3,512,264. His 120 wins was tops among all apprentices in 2018 and he finished second in earnings in that category.

As for goals this meet, Hamilton wants to continue trending up, but he knows anyone has their hands full trying to dethrone Cabrera on his home track.

“Aw heck, nothing away from that feller,” Hamilton said of Cabrera. “He works hard and does a good job. I’d just like to win a few more than I did last year here. I’d like to top that off. Being in the top couple of riders is pretty fun.”

Live racing at Remington Park continues this week with a Thursday, Friday, Saturday schedule, Sept. 1-3. First post time is 7 pm-Central each night.

Tracked by more than 171,000 fans on Facebook and 10,600 Twitter followers, Remington Park has provided more than $298 Million to the State of Oklahoma general education fund since the opening of the casino in 2005. Located at the junction of Interstates 35 & 44, in the heart of the Oklahoma City Adventure District, Remington Park features the Grade 3 Oklahoma Derby and Grade 3 Remington Park Oaks on Sunday, September 25. Thoroughbred racing continues through December 17 with simulcast racing daily, and a casino that is always open! Visit for more information.