A publication of the Kentucky Center for Public Service Journalism

A personal memory of legendary horseman Tom Gentry, ‘master of sales party,’ who died Tuesday

In May of 2012, our then-regular columnist Robert Treadway wrote a terrific series of columns on the Kentucky horse industry as he lived it and remembered it. Among those was this memory of legendary horseman Tom Gentry. We are sharing it in the wake of Tom Gentry’s death on Oct. 31 at age 80. He was an owner, breeder, consignor and racing official over a long and celebrated career. He is survived by his two children and five grandchildren. Visitation at Milwards Funeral Home is today. Funeral mass will be Nove. 3 at 10 a.m. at St. Paul Catholic Church on Short Street. Burial is private.

By Robert Treadway
Special to KyFoward

My plane touched down in Los Angeles on Valentine’s Day 1991, and that’s about my last clear memory of the week. The marble floor was pink, and fake palm trees were everywhere inside the airport. Or maybe they were real and in pots. Who knows. It was my first time in LA, and I was in a new world: There wasn’t a tobacco barn in a thousand miles.
Then I heard the booming voice that is famous in the horse business, “My man BOB!” I was there to take depositions in one of the many lawsuits in which I represented Tom Gentry, the man who revolutionized the horse business and became the first victim of its downturn in the ’80s.
Tom, more so than any other breeder and owner, brought the modern world of marketing and debt-based financing to thoroughbred racing. I’m not saying Tom Gentry is the first person to buy a horse with borrowed money, but he rather perfected the art. In the ’80s, most owners’ idea of marketing was preparing a pedigree sheet and maybe a photograph to hand out at the sales.

A young Tom Gentry (Paulick Report photo)

As New York Times writer Steven Crist pointed out in his book, “The Horse Traders,” Tom didn’t stop there. He had rulers made with horses’ names on them. He had fancy pens made with his “Tom Gentry Farm” logo on them. His most popular giveaway was the Tom Gentry watch.
In truth, it was no more than those $20 watches they sell in ads in airline magazines, but its face had “Tom Gentry Farm,” and his famous blue and yellow racing colors on it. I finally figured out that a witness was going to be helpful if he showed up to testify wearing a Tom Gentry watch.
And he had parties. Tom was the master of the sales party, but the only one I got to attend was his last, and arguably greatest. A thousand invited guests were treated to lobster, caviar, champagne and live entertainment by Neil Sedaka, along with dancing to The Platters. He was also a master of party accounting, carefully dividing up the cost of the party among the owners whose horses he consigned.
Once Tom was asked on the witness stand who he invited to these parties, “I invite every horseman in the KNOWN WORLD!” he testified, and that was about right. Because here’s the other thing you need to know about Tom Gentry: He is a serious horseman, a serious student of pedigrees and one of the few I’ve heard old-timers refer to as a “real horseman,” praise they don’t give out lightly. I don’t know how many times I’ve thrown out an obscure breeding reference, only to have Tom explain the lines to me chapter and verse, including where I was wrong.
Tom’s theory on promoting was simple: “No one is going to spend a million dollars on a horse because I give him a watch or invite him to a party. But if he’s thinking of spending a million dollars on a horse, and it comes down to my million dollar horse and someone else’s, I think he’ll lean a little toward a guy he likes.” Good advice.
Tom picked me up at the airport in LA, and from there the whirlwind began. I’m not sure who exactly we met with, or in many cases why, but I do have a memory of a meeting in an office in a car wash in Beverly Hills, which had a picture window looking onto a stream of Mercedes and Rolls Royces slowly cruising by, soapy but elegant, and somehow surreal. We talked horses, I’m sure; that’s why I was there, but we talked a lot of other stuff, too. We were taking depositions in one of the lawsuits arising out of Tom’s landmark bankruptcy, the first big one in the equine industry, before Calumet set the gold standard for equine bankruptcies in the ’90s.

Tom Gentry

Tom didn’t ask the same type of technical questions many clients asked. In LA, a typical Tom question was, “BOB, what if we just go somewhere and get DRUNK and don’t show UP at this thing?” I never took him up on it, so we didn’t find out.
At one point, while Tom was on a date in LA, I had to go have dinner with another horseman, with whom Tom was trying to work out a deal. Tom and I had gone over numbers, horses and breeding records, and I thought I knew his mind. Tom got back to the house in the middle of the night, and woke me up, “Did we make a DEAL??”
I said that sadly we had not. “What did you offer him?” Tom asked. I told him in some detail, thinking I’d proposed a good deal, that had been turned down. “You offered him WHAT!” Tom exclaimed, “And he turned it DOWN? There’s where two fools MET!” His ire didn’t keep him from taking me, with some of his friends, out on the town the next night as only he could. I’m not sure I can recreate our route, though it involved dinner at the Press Club in Santa Monica – chateaubriand, rare, quite good, with one of those big cabernets they were drinking then – and dancing at the original Top of the Mark. Thankfully, both Tom and I were a lot younger then, and I had shed some weight, in training for my second nuptials (that one didn’t work out, either), so we survived.
His success at the breeding shed was legendary. His great foundation mare was Crimson Saint, who Tom was lucky enough to get in foal by Secretariat, in what turned out to be his last foal crop, and lucky enough to get a filly, by a sire who became known as a sire of broodmares. I was there at Keeneland, when the bidding went to a million and a half, a million eight, and Tom shouted out at the top of his lungs, “If it goes to two million, I’ll throw in my COAT!” taking off his madras plaid – by that time as big as a horse blanket itself – and waving it. The bidding finally ended at $2.1 million, leading Tom to quip, “If it had hit two and a half, I’d have thrown in the PANTS!” The buyer? D. Wayne Lukas, who was quoted in the press as saying that the filly was the only thoroughbred he’d ever scored a perfect 10 out of 10 on confirmation. As sales watchers know, confirmation is in the eye of the beholder, and good sales prep is half the battle there: Tom knew this when half the breeders in Lexington were sending horses through the ring with burrs in their tails.
Because of a conviction I still think unfair, Tom had to spend a few months in federal prison. I drove down to Manchester to see him the day before Thanksgiving, and he was cheerful as usual. He told me about the prison’s gospel choir, giving them his highest praise, “BOB, if these guys were singing in Lexington, we’d go see them on Saturday NIGHT!” Shortly after, Tom proved that he could be as funny in writing as he could in person. He had gotten his telephone privileges denied for having referred to his counselor as a bitch to someone else on the phone – they were monitoring his calls. The primary thrust of the letter was that he was right in his analysis and spent several paragraphs explaining why. My partners wanted to have the letter framed.
Ultimately, Tom was philosophical about his time “in camp,” as he called it, at one point suggesting that it would be a good experience for everyone. I didn’t know then that in time, I’d have the same experience (though not for quite as long, and closer to home), and the same assessment of it.
The serious point of the letter was to share with me a few citations from some legal research one of our mutual friends, a lawyer also spending some time in camp, had done concerning Tom’s telephone issue. Not every client gives you jailhouse research. Tom also gave me a recipe for Jailhouse Dip, a mixture of various canned chip dips that my son eats to this day. In that pre-Internet time, copies of the Code of Federal Regulations were scarce and expensive, (today Internet access is free), but our law firm library had one, and I was amazed to find an entire volume of regulations concerning telephone calls by inmates in federal prisons. Once again, I had the idea that I was a long way from home.
I didn’t know Tom very well when he was flying high, but I certainly rode all the way down with him, from the time he had a million-dollar house in a Los Angeles suburb, along with his Tom Gentry Farm, his thoroughbred breeding stock, and his penthouse in the old Radisson downtown, now the Hilton, to the time his creditors took it all. The horse business had tanked, but the banks’ debts didn’t reduce to match it, and there wasn’t enough to go around.
There were big fights, and not content to comment himself, he put words in my mouth, too. His bête noir in those days was Natalie Wilson, lawyer for his former wife. She and I got along fine, but Tom saw her as the personification of all evil. At one point, a trip to the Channel Islands – between England and France — was necessary, on the theory that Tom may have hidden some assets there, and Natalie moved that Tom be required to pay her travel expenses for the round trip. Tom, as he said, “told it all over Short Street that Bob said he didn’t mind paying for Natalie to go OVER there, he just minded paying to bring her BACK . . .”
The Radisson condo figures into many Tom Gentry stories. It started almost as a private clubhouse for Tom and his friends. When I was trapped and kidnapped and marched to the Radisson from my law office high atop the Lexington Financial Center, I feared the worst, but found only that Tom had conspired with my law partners to give me a bachelor party there, in anticipation of those second nuptials. I mentioned that we were younger in those days.
Toward the end, Tom lived in the condo himself, along with his Australian sheep dog, Lucy. When Lucy had a particular need, Tom would take her to the elevator, push the lobby button, and send her down by herself. She would go outside, onto Vine Street, do her business, and come back into the lobby, where one of the busboys (whom Tom tipped well) pushed the elevator button for her, and hit Tom’s floor. Many times I’ve been there when she came back to the door and barked to be let in. Apparently once she caused havoc among a ministerial group she mistook for sheep that had gone astray.
Despite all he went through, and he went through more than people know, Tom never got bitter. But one time, concerning Christmas, he told me, when my son was small, “Bob, don’t EVER tell him there is no Santa Claus. Let him believe it til he’s TWENTY if he will, because let me tell you, no one else but Santa Claus will ever do anything for you . . .” Perhaps for that reason, Tom loved Christmas. This past Christmas, I shared a story on Facebook, about a Christmas in which I picked up a bit of tattered tack in a barn, and laid it in the ashes of our fireplace so that William could find a bit of reindeer tack, to hold the illusion one more year. Who taught me that trick?
Tom Gentry.
I don’t see Tom much anymore, but he still has the same style. I fear for his health, with all those years of all that weight, but perhaps his style will get him through. He apparently had a medical emergency that required the EMTs to come to his home recently, and ever grateful, Tom was later seen treating them to a day of races at the Thoroughbred Club. I’m sorry I wasn’t there with them. He used to invite Joyce Clayter, the constable who constantly served papers on him, to his parties. When my old law firm had a charity auction, each partner was asked to put in one item to sell. My item? A day at Keeneland with Tom Gentry and me for two guests, all expenses covered – bets on your own. It brought the highest price at the auction, and I’d like to think we didn’t disappoint with either our stories or handicapping information.
Robert L. Treadway is senior policy analyst at Kentucky First Strategies, LLC, a full-service political consulting, lobbying, and governmental relations firm. In his role as a legal consultant, he also provides legal research and writing services to attorneys and law firms throughout Kentucky. Bob has a life long interest in Kentucky history, which he pursued as a student at Transylvania University, where he graduated with a major in history and minor in political science, and was an award-winning editor of Transy’s student newspaper, The Rambler. He is a graduate of Harvard Law School, where his media activities included scriptwriting for Harvard Law Professor Arthur Miller’s TV series, and Miller’s role as legal editor on ABC TV’s “Good Morning, America.” He writes, posts and Tweets about Kentucky history.

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