A Kentucky double: Can trainer take home Oaks-Derby double?

A win in the Kentucky Oaks on Friday has Todd Pletcher halfway toward a milestone last achieved 61 years ago.

The trainer can accomplish the rare feat by winning the Kentucky Derby on Saturday, a goal that has required a lot of hours at Churchill Downs.

Pletcher will saddle a record-tying five entries in the 139th Run for the Roses — including Revolutionary, the early co-favorite at 5-1 with Goldencents after betting opened Friday. Pletcher had four fillies in the Oaks and saw his bid for history begin with 38-1 long shot Princess of Sylmar rallying down the stretch to win the $1 million race.

The trainer now aims to become only the fourth to pull off the Oaks-Derby double and the first since Ben Jones, who won the 1952 Oaks with Real Delight and Derby with Hill Gail. Jones also did it in 1949.

Asked after the Oaks if he's thinking about history, Pletcher said: "We're the only ones with a chance anyways."

Hall of Fame jockey Mike Smith is definitely pondering it, for Pletcher and himself. Smith rode Princess of Sylmar and will mount Palace Malice, trying to become the first rider to double since Calvin Borel won the 2009 Oaks aboard Rachel Alexandra and the Derby with Mine That Bird.

The scenario has crossed Smith's mind.

"We've done the first part," he said.

Borel will be trying to thwart the second part of that attempt aboard Revolutionary.

Whether the weekend ends happily for Pletcher or leaves him ready to move on to the Preakness in Baltimore in two weeks, the numbers give him a good chance to make history. But then, he's always had quantity at the Derby, where he's saddled 31 starters and won in 2010 with Super Saver.

Pletcher also has quality in Revolutionary, unbeaten Verrazano, Overanalyze, Charming Kitten and Palace Malice. The first three figure to make the biggest noise in the 19-horse field.

"We laid out a plan to get here with them, and it's all come down pretty much like we hoped," Pletcher said.

But as Friday's Kentucky Oaks showed, things work out for Pletcher even when the plans change.

Princess of Sylmar was expected to be a distant finisher behind 8-5 favorite Dreaming of Julia, in the race with 9-2 choice Unlimited Budget and 48-1 shot Silsita. Instead, she and Unlimited Budget helped Pletcher claim win and show in the Oaks thanks to a wicked stretch run from fourth to chase down Beholder.

Dreaming of Julia had a troubled start but recovered to finish fourth.

Princess of Sylmar earned the Oaks' second-highest payout at $79.60 behind Lemons Forever's return of $96.20 in 2006. Pletcher earned his third Oaks win after Ashado in 2004 and Rags to Riches in 2007. Both fillies went on to earn year-end championships.

"We're pleasantly surprised with her effort and her win," said Pletcher, who had considered not running Princess of Sylmar after a subpar early workout.

"She's a good filly — we knew that all along. We took her out of her natural running style last time. This time, she made that good run and got it done."

Pletcher now moves on to the Derby and a chance to achieve something that hasn't been done in more than half a century. That a long shot put him on the brink could be considered an omen, but he's worked hard to create some luck.

"I know Todd has a lot of the bigger players in the game," Princess of Sylmar owner and breeder Ed Stanco said. "I've been with Todd for 10 years, just one at a time. It's been a very well-planned approach to how to go to the races.

"We took our time with some smaller, not so successful (horses). To me, there's no better trainer that he can do this with this kind of filly."