Cameron Milligan is winning a different type race these days.

Roughly a decade after his running career ended, Milligan saddled his first winner as a Thoroughbred trainer when Arkansas-bred It’s a Rainy Day ($53) captured the second race on Jan. 24 at Oaklawn, an open $20,000 maiden-claiming sprint, for G-Paw Racing. It’s a Rainy Day, who was ridden by Rocco Bowen, was Milligan’s fourth career starter.

Milligan, 28, is the son of trainer Eddie Milligan Jr. and the nephew of Allen Milligan, Oaklawn’s leading trainer in 2009. Both Eddie Milligan Jr. and Allen Milligan are also based this winter at Oaklawn.

It’s a Rainy Day’s victory came less than a month after Eddie Milligan Jr. scored his first career Oaklawn stakes victory when Seize the Night, owned by Willis Horton Racing (Kevin Horton), captured the $175,000 Tinsel for older horses on Jan. 5.

“I was extremely happy,” Eddie Milligan Jr. said of his son’s landmark victory. “Very proud.”

It’s a Rainy Day, who began his racing career with Allen Milligan, was also Cameron Milligan’s first career starter, finishing fourth in a lower-level maiden-claimer Dec. 14 at Oaklawn. It’s a Rainy Day then finished sixth against $15,000 Arkansas-bred maiden claimers on Dec. 27 at Oaklawn.

“He ran good for me that day,” Milligan said of the gelding’s first race. “I was thinking maybe his second race was going to be maybe one of the days that he would finish in the top two. Unfortunately, it wasn’t his day that day and I had to switch jockeys. I put Rocco Bowen on him that day and Rocco got off of him after that race and said: ‘If you get me back on him, I’ll win with him.’ Going into the race, I was feeling pretty good that he was going to run better. So, it was just exciting to see him actually do it.”

Milligan grew up in Murchison, Texas, a town of 500 about 80 miles southeast of Dallas. As a teenager, Milligan got on horses for his father, a former jockey who then ran nearby Twin Oaks Training Center, where he broke, among others, champions Will Take Charge and Take Charge Brandi for the late Arkansas owner Willis Horton.

Cameron Milligan, however, didn’t immediately follow in the footsteps of his father or uncle.

Cameron Milligan excelled in distance running and cross country at Brownsboro (Texas) High School, graduating in 2015 as a district champion. He competed one year at Tarleton State University in Stephenville, Texas, before lower leg and foot problems ended his competitive running career.

Milligan graduated from Tarleton State in 2020 with a degree in kinesiology and an eye toward coaching track/cross country in high school or college. Instead, he spent the next 2 ½ years building custom homes in Stephenville, then roughly 18 months as a roofing supervisor in Austin, Texas.

“I had never really planned on coming to the racetrack,” Milligan said.

But during Milligan’s time in Austin, Eddie Milligan Jr. accepted an offer to train privately for Kevin Horton, who was continuing his father’s high-octane racing operation following his death in October 2022. Eddie Milligan Jr. won 90 races as a trainer between 1994-1997.

“All my dad did when I was growing up was break horses,” Cameron Milligan said. “I used to hear the stories of him being a jockey and a trainer before I was born. I never got to experience that with him. So, when he said he was coming back to the racetrack, I told him I would do it with him.”

Cameron Milligan followed his father to Remington Park, where Eddie Milligan Jr. made his training comeback in September 2023.

“Just started getting back into it,” Cameron Milligan said. “I used to ride horses in high school for my dad, but it had been a while. I came back and started to get back on horses, try to re-learn everything. Just was eventually kind of his assistant when we went to Remington and finally got my assistant trainer’s license here last year.”

Milligan took out his trainer’s license in November 2024 and began the 2024-2025 Oaklawn meeting with two horses – It’s a Rainy Day and Malachi, who is co-owned by G-Paw Racing (Texan Gregory Pelzel) and the trainer’s older brother, Caleb. Pelzel, Cameron Milligan said, is a longtime family friend, Milligan, on behalf of G-Paw and Caleb Milligan, claimed Icy River for $10,000 Jan. 24 at Oaklawn, expanding the trainer’s stable to three.

“Right now, just trying to rack up some more clientele and get some more horses,” said Cameron Milligan, who is stabled with his father in Oaklawn’s Will Take Charge barn. “Five years? I’d like to have about 30 horses and come back to Oaklawn. Really from there, just try to figure out what route I want to take after Oaklawn. This is home for me. I’ve got a house here, so I’ll aways come back here. After that, it’s just trying to figure out if I go to Kentucky or Texas.”

Cameron Milligan said he will probably be based this summer at Lone Star Park in suburban Dallas.