"I'm not as excited about having five in there," he said. "I want to have one that wins."
The 39-year-old trainer has come close twice before. He finished second to Barbaro with Bluegrass Cat last year and second with Invisible Ink in 2001.
This year, he's saddling Any Given Saturday, Circular Quay (pronounced key), Cowtown Cat, Scat Daddy and Sam P.
"I still don't feel like in years past that we've brought the best horse to the race," he said. "I'm hoping this year that maybe one of ours is."
Two of his horses - Circular Quay and Scat Daddy - are coming off extended layoffs, and history dictates Derby winners run within four weeks of the first Saturday in May.
Barbaro proved the exception last year when he won after a five- week layoff.
Three of Pletcher's previous 12 Derby starters had layoffs longer than three weeks going into the race, so this year the trainer is in uncharted territory. Louisiana Derby winner Circular Quay will have had an eight-week break, while Florida Derby winner Scat Daddy comes in off a five-week rest.
"Most of the final preparations have been a little further out than they would have normally been. So that's one adjustment that we've made trying to improve on our Derby results," he said. "Bring in maybe a little fresher horse than we have in the past."
That represents a change in Pletcher's thinking. This year, he's chucked tried-and-true Derby trends and is relying on the tendencies of his own horses.
"The horses that we train tend to do much better with time between races and I just don't see why that wouldn't apply to the Kentucky Derby," he said. "I know you can take all the historical facts and stats and all that, but if I do that I'm ignoring the most important data and that's on the ones I train."
Except for the Triple Crown races, Pletcher has enjoyed huge success during his 11-year career, giving him the confidence to deviate from the norm.
"I think you just have to be comfortable with what works best for you and for your horse," he said.
Pletcher has won three consecutive Eclipse Awards as the nation's top trainer. His horses earned more than $26.8 million last year, surpassing his previous record by $6 million, and his 100 stakes wins broke the record of 92 set by his mentor, D. Wayne Lukas.
The low-key Pletcher lets everyone else obsess about why he has yet to win the Derby, Preakness or Belmont Stakes.
"I don't think Todd is feeling that pressure because he's having such a great run the last couple years," Lukas said Tuesday. "He's going to win one. But sometimes in sports, you get a long run with some great athletes and great people that don't get the ring."
Saturday, Pletcher will join Lukas, a four-time Derby winner, and two-time winner Nick Zito as the only trainers with five Derby starters in the race's 133-year history.
"He's got a solid bunch," Lukas said. "I don't think he'll have a Nick Zito."
Lukas won with Grindstone when he saddled five in 1996, while Zito was shut out with his five in 2005.
Pletcher's losing streak in the Derby hasn't scared off any of his wealthy clients, whose enthusiasm for having horses in America's greatest race has rubbed off on him. "These people who are very, very successful in their own endeavors in life, but they're really fired up," he said. "That makes it a lot of fun for us to see how excited they get about it."