Problem was, his horse was nearly too good.
"Goodfellas" actor Paul Sorvino got the biggest applause this year as he serenaded the media crowd at Churchill Downs with a rendition of "My Old Kentucky Home" in his best operatic voice.
Always Dreaming won by 2 3/4 lengths. Irish War Cry remained at 5-1. throughout the day, then went to 9-2 odds right before the race.
The strong wagering figures on the Derby were due in part to a wide-open, 20-horse field that led bettors to stretch their bankrolls in the hopes of catching a large payout in the exotic pools.
Early favorite Classic Empire finished fourth, one length out of the money, while fancied McCraken finished eighth and Irish War Cry was 10th across the line, 16 1/2 lengths back. Once they shook loose of Battle of Midway at the mile mark, everyone else was running for second place.
Velazquez described the trip, "Todd and I talked about it a lot, to make sure to come out of there running to get the kind of position we would like to have and be comfortable".
Always Dreaming was a bit wild in his training at Churchill during the week.
Velazquez and Pletcher each won their second Kentucky Derby thanks to Always Dreaming, though their first titles came separately.
The track was far from ideal, but it also wasn't bad enough to compromise anybody's chances, although a couple of trainers may differ. "It's special to win one with Todd". He paid $4.60 and gave trainer Chad Brown a second consecutive win. Yet Pletcher's frustrations in the sport's most high-profile race were well-documented. "The most important thing to do is bring the best horse to the Derby, and that's what we were able to do". Before Saturday, he was 1-for-45.
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"We needed one together", Pletcher said.
It was up for grabs in the final furlong with several horses still having a shot.
The partnership that owns Always Dreaming - known as "Brooklyn Boyz Stables" - includes Florida Panthers owner Vincent Viola.
Classic Empire's record also includes winning the Breeders' Cup Juvenile, a race for two-year-olds, last season.
It was another five lengths back to Battle of Midway, who followed Always Dreaming around the track on the inside and held on for third.
The 66-year-old native of Chicago, who was the announcer at New York Racing Association from 1990 until his retirement in 2014, purchased a small ownership share of Always Dreaming April 19 through the West Point Thoroughbreds partnership that owns a minority interest in the son of Bodemeister. It was the time of the race, 1:47.47, that got Pletcher's attention.
When it was time to run, Always Dreaming got serious. And after the dazzling work the following Friday, Pletcher was concerned the colt still wanted to go. His story has captivated many fans and apparently their wallets, too.
Velazquez and Always Dreaming fired out of the gate and sailed along the sodden track as if riding the tide. Ben Colebrook trains the victor, whom Jose Ortiz rode. I said why don't we just name it Dreaming? "We think he can handle this distance". "But he ran like he loved it". The Preakness will ultimately determine whether or not a Triple Crown could be had at the 2017 Belmont Stakes.
"Johnny of course rode him great", Pletcher said.