When Win Win Win came to trainer Mike Trombetta last year, the Live Oak Plantation homebred found a niche with the rest of the 2-year-olds in the barn. He trained, learned, progressed, moved forward, moved backward, moved forward again. Nobody was really thinking Kentucky Derby, at least not any more than any owner or trainer does with an unraced 2-year-old.

“He came with the rest of the 2-year-olds last year and we trained along,” Trombetta said. “It took us a little while to get him ready to go. The first race, I entered in a turf race at Laurel. It was the late part of season and the idea was, ‘We’ll see how he handles that.’ After that it was going to be all dirt anyway.”

Rain forced the Nov. 3 maiden race off the turf, and Win Win Win won by a half-length in a field of 10. The son of Hat Trick showed more speed than Trombetta expected, racing near the front throughout and getting 5 1/2 furlongs in 1:04.61. A month later, Win Win Win shaved more than two seconds off that time while winning an allowance race on the dirt at Laurel. The dark bay colt won by 6 1/2 lengths, signaling there might be more in store.

“He started to gather my attention pretty quickly then,” Trombetta said. “The maiden condition’s gone, the a-other-than condition’s gone, now you’re stakes caliber.”

Win Win Win finished second to fellow Fair Hill Training Center-based 3-year-old Alwaysmining in the Arnold Heft Stakes Dec. 29, overcoming a sloppy start to erase a big deficit but coming up 1 1/2 lengths short going 7 furlongs. Much like the wins, the loss gave Trombetta some information and the trainer circled the 7-furlong Pasco Stakes at Tampa Bay Downs in January. Win Win Win aired, again breaking a little bit slowly but rolling home by 7 1/4 lengths and setting a track record of 1:20.89.

As a 3-year-old with a January stakes win in Florida, Win Win Win was suddenly on everybody’s radar.

“After the race in Tampa, that tells you he can run,” said Trombetta. “It was just a matter of whether he can run at this level with this kind of horses. He showed that he can.”

Of course, the Pasco brought up another question.

“Will he go two turns?” Trombetta said of the backside discussions. “Short of ‘I hope so,’ I wasn’t sure how to answer that.”

The trainer left Win Win Win at Tampa with eyes of finding out in the Tampa Bay Derby March 9. Eleven lengths behind after a half-mile, he made a mild run outside horses to reach contention by the top of the stretch but settled for third behind Tacitus and Outshine. The two-turn answer was a definite maybe, and Win Win Win would get one more chance to prove it – this time after shipping home to Fair Hill. Off two works over the Tapeta track, the Florida-bred finished a fast-closing second in the Blue Grass at Keeneland April 6. He was not threatening 3 1/2-length winner Vekoma, but did pass everybody else while rallying from 13th and nipping Signalman by a nose for second.

That nose pushed Win Win Win into the Kentucky Derby with 50 points, while Signalman is outside the frame with 38. Trombetta was proud of his horse, who steadied while in the midst of his run on the final turn.

“It was one of those races where it looked like we had a chance, it looked like that chance went away and then it came back again,” he said. “That’s a credit to him. He stayed in there and kept battling. We’re learning with him. It was his second two-turn race and it was pretty clear he was running on. I was pretty happy with it. I don’t think two turns is a problem.”

Win Win Win has lived up to his name and won three races (with two seconds and a third) and $367,300 earned in six starts. If all stays on target, Trombetta will have his first Derby starter since Sweetnorthernsaint in 2006.

“It’s been a while,” said the trainer. “It’s a pleasure to have a nice 3-year-old this time of year. He’s doing everything we’ve asked of him so far. Hopefully he’s got a little more left to give.”

NOTES: Win Win Win returned to Fair Hill after Keeneland and will stay at the Maryland facility for another two weeks (give or take) . . . A slight favorite after winning the Illinois Derby, Sweetnorthernsaint finished seventh behind Barbaro in the 2006 Derby, the finished second in the Preakness . . . Eclipse Award winner Irad Ortiz Jr. rode Win Win Win in his last two starts, but Monday opted for Improbable from the Bob Baffert barn for the Derby once Jose Ortiz chose Tacitus. Trombetta told Daily Racing Form that Julian Pimentel, aboard for all three of Win Win Win's wins, will get back aboard in Kentucky. It will be the Maryland-based jockey's first Derby mount . . . Fair Hill's Alwaysmining tries to earn his trip to the Preakness in Saturday's Federico Tesio at Laurel.