In a way, there has been a little bit of Frank Sinatra in trainer Bob Baffert.
That might seem like a strange thing to say about a man with a reedy voice and a flowing mane of snow-white hair. But it's true.
Catch him on the right day, and Baffert is as charming as anyone in sports. He can hold the attention of the room — or a throng of media outside a horse barn — better than anyone else in thoroughbred racing. He can do funny and witty one minute, dry and sarcastic the next. It's rare to see him without sunglasses, even indoors, a habit that only adds to the Baffert mystique.
But he can also be temperamental and stubborn. Cross him, and he won't let you forget it, as a handful of journalists have learned over the years. The 57-year-old Californian doesn't mince words or seem to worry about whom he offends. In the past, he has insulted fellow trainers, feuded with jockeys and shamelessly courted the media. To some, he is borderline insufferable. But like the Chairman of the Board, he does it his way, and he makes no apologies for it.
Yet no matter how you feel about him, you can't argue with his success as a trainer. Baffert has won the Kentucky Derby three times, and if he wins Saturday with morning-line 3-1 favorite Lookin At Lucky or long shot Conveyance, he'll become just the fourth trainer to win it four times.
"I don't think about how many I've won," Baffert said. "Just to get back here and have a legitimate chance feels pretty good. It helps you get more business because there are always owners out there that don't know where to send their 2-year-olds. It's like a college coach.
"You win the championship, you're going to get good young players who want to play for you."
Part of what makes Baffert's success so compelling is that he typically shrugs off horse racing conventions.
Thoroughbred racing has historically required trainers to be early risers. It's not unheard of for a trainer such as Todd Pletcher to be out of bed at 4:30 a.m. That's not Baffert's style. He doesn't kill himself getting to the track; he has never thought it necessary. But that doesn't mean he doesn't work hard when he's there.
"Bobby is a great horseman, but people expect you to be at the barn at 5 a.m. and follow the traditional way," said Mike Pegram, one of the co-owners of Lookin At Lucky. "Bobby is a wise guy. He works when he wants to work. He's very intense, but you know what? He's got a life, too. He doesn't have to live at that barn. A lot of people think horse trainers should be at that barn 24-7, but when Bobby is at that barn, he doesn't miss nothing. He's a sponge."
Pegram knows Baffert as well as any other owner in the business. They have worked together since Baffert started training quarter horses in the mid-1980s. They've been through a lot together — marriages, divorces, children and grandchildren. They are business partners second, friends first.
"He deserves to be the winningest Kentucky Derby trainer of all time," Pegram said. "When you see how he has dominated this race over the last 15 years, it speaks for itself."
For a while, Baffert made winning the Derby seem almost routine. He lost to D. Wayne Lukas and Grindstone by a nose in his first Derby in 1996 with Cavonnier, then won with Silver Charm (1997) and Real Quiet (1998). Real Quiet, owned by Pegram, came as close to winning the Triple Crown as any horse since Affirmed did it in 1978. Real Quiet won the Derby and the Preakness, then was beaten by a head bob at the wire in the Belmont by Victory Gallop.
"The first couple times I came [to the Derby] with Bob, I thought this thing was pretty easy to win," joked trainer Eoin Harty, who worked for several years as an assistant to Baffert but now trains on his own and has American Lion in this year's Derby. "I thought you just showed up with your horse from California and got your picture taken."
Baffert won his third Derby with War Emblem in 2002 and looked as if he were about to win his fourth last year with Pioneerof the Nile until Mine That Bird came from the back of the pack to secure one of the biggest upsets in the history of the race. Eight years might not seem like much of a drought to most trainers, but it does to Baffert.
"It's on my resume," Baffert joked this week, "but I've forgotten the feeling."
"People don't understand how competitive Bobby is," said Pegram, who owns a chain of McDonald's restaurants in Arizona and a pair of casinos in Nevada. "He is a super-good horseman who marches to a different drummer, but the intensity he has and the knowledge he has is unmatched. He knows what he wants, and he treats each horse differently to bring out their strengths. That's why he's one of the best trainers the good Lord ever put on this earth."
Baffert's competitive fire was on display earlier this year at the Santa Anita Derby, when he didn't hide how furious he was with jockey Garrett Gomez after Gomez took Lookin At Lucky inside to the rail and was fortunate it didn't result in a wreck. Baffert called the ride "horrendous" and "ridiculous," saying Gomez had put Lookin At Lucky in a position where he could have been hurt. He saved some of his criticism for another jockey, Victor Espinoza, who nearly wrecked Gomez.
The incident led to speculation that Baffert might consider replacing Gomez for the Kentucky Derby, but Baffert eventually was able to laugh it off. When Lookin At Lucky drew the No. 1 post position in the Kentucky Derby draw, Baffert joked that Gomez was finally going to get his way.
"He likes to be inside and get a horse in trouble, so now he'll get his chance," Baffert said.
Baffert has mellowed somewhat in recent years. Several years ago, he was livid when a Los Angeles Daily News reporter wrote an article before the Derby that mentioned his divorce from his first wife, Sherry, and his decision to pursue a public relationship with Louisville native Jill Moss. He felt that his personal life, and especially Moss' — to whom he is now married — should be off-limits.
But this week, when asked by a reporter in a news conference what inspired him to continue training thoroughbreds, he pointed, unprompted, to Jill, who just happened to be sitting behind the reporter. The couple has a 7-year-old son, Bode.
"She's what keeps me going," Baffert said. "Sitting right behind you.
"She really enjoys it. She's my biggest supporter. But you know, my whole family supports me. Everybody is excited because there is nothing like the Derby. We just came from the Derby museum, and we all came out with tears in our eyes. It makes you realize that just to be here is really special. To be part off all this is amazing."