After setting a fast early pace, Masochistic was eased in the stretch by jockey Victor Espinoza and came in 18 3/4 lengths behind the winner, Tough Sunday.
The 2015 Triple Bend (G1) victor, who also won the 2015 Kona Gold (G2) and the 2016 Pat O'Brien (G2), last ran well in the 2017 Triple Bend (second) and ended his racing career with three far-back finishes. In those three starts he finished a combined 46 lengths behind the winners.
"He's 100% sound and he's going to have a career as a trail horse. He's had enough and he's telling us that," Shamlian said. "He's too good of a horse, and we're going to do right by him. He's given us the message and we're going to listen. We're going to find him a good home."
The 8-year-old Sought After gelding retired with an 8-3-0 record from 18 starts and $860,895 in earnings.
"He's been so much fun. I come out in the morning for every breeze, and I wish that could go on forever," Shamlian said. "I never thought I'd have a horse as good as he was, and I'm never going to have a horse as good as him again."
After he was moved to trainer Bob Baffert in 2017, Masochistic returned to racing with a fast-early, tired-late fifth-place run, similar to the Sensational Star, in the Donald Valpredo California Cup Sprint Jan. 27.
"To be honest, I did the mourning last race," Shamlian said. "I knew it was coming, and of course I'm sad, but I was kind of prepared for this moment. The last race, when he ran that way, it killed me."
Masochistic was a top-level sprinter in California for much of his career, but he was also embroiled in controversy multiple times. It started with his first race, when he was trained by A.C. Avila.
On debut in March of 2014, Masochistic finished fifth in a state-bred maiden race at Santa Anita, but he was eventually disqualified to eighth after he tested positive for elevated levels of the tranquilizer acepromazine. Racing officials also questioned the ride of jockey Omar Berrio.
In Masochistic's next race, on the Kentucky Derby (G1) undercard in 2014, the California-bred won an open maiden special weight race at odds of 2-1. Kentucky Horse Racing Commissioner Ned Bonnie called for the wagering on the race to be investigated, because he felt Churchill Downs may have been used to carry out a betting coup.
The California Horse Racing Board eventually suspended Avila for 60 days and fined him $10,000 for the medication violation in the debut race, and Masochistic was moved into the care of trainer Ron Ellis, where he earned his graded glory.
But Masochistic came up with another overage following his second-place run in the 2016 TwinSpires Breeders' Cup Sprint (G1), which was his eighth start for Ellis. This time the overage was for the anabolic steroid stanozolol.
Masochistic was disqualified from his second-place finish because of the test, which discovered 30 picograms per milliliter of stanozolol and 161 picograms of its metabolite 16-hydroxy stanozolol. A picogram is one trillionth of a gram.
After an extended hearing process, Ellis was suspended for 60 days and fined $10,000 in December of 2017 and just returned to training horses this month.
Masochistic had two more starts with Ellis—a second-place finish in the 2017 Triple Bend and a 13th-place run in the Churchill Downs Stakes Presented by Twinspires.com (G2)—but was moved to Baffert after the trip to Kentucky.