Lamoreaux: When Sales Were Showtime – Remembering Tom Gentry

Right about this time of year, around these parts, when the first snow flurry flies past the ears, thoughts turn to “the list.”  It came into this reporter’s life many moons ago when my CBS colleague Charles Kuralt suggested we think about making a list and naming names on our yearend broadcast of those who earned an obituary that year of 1980 – Jesse Owens, Alfred Hitchcock, Colonel Sanders – and not only the movers and shakers but those who had left a smaller but no less significant imprint on our lives, like a sculptor or a comedian or maybe even a Thoroughbred.

Earlier that year on Belmont Saturday, I had gone around the corner from our “Sunday Morning” offices to an Off Track Betting shop in New York City to bet the Kentucky Derby winner Genuine Risk across the board in the final leg of the Triple Crown.  I asked Kuralt if he wanted a piece of the action.

“No thanks,” he said, “but you can get me five across on that longshot, Temperence Hill.”  And when the Joe Canty-trained 53-1 shot won and I presented Kuralt with a large wad of small bills, he said with a half-smile on his face, “Oh, and be sure to let me know when old “Temperence” leaves this earth because he sure is going on that list of mine.”

Which brings me to a name that’s prominent on my list this year – a trend-setter in the breeding industry in the 1980s.  I’m talking about Kentuckian Tom Gentry, who died recently at the age of 80.  What you will read next does not pretend to be a complete obituary, but rather a collection of anecdotes about one of Thoroughbred racing’s maverick game-changers.

My friend Tom was a “horse trader” of the highest order, which meant that he had just as many enemies and rivals as friends.  But he had a P.T. Barnum streak in him and a great, big heart that made you love being around him when he started to do his dance.  Tom was a bootstrap guy.  His father Olin had been a farm manager for 60 odd years and saw his bosses win 13 Triple Crown races and large pots of money for themselves.

Tom Gentry, left, with his father and son, both named Olin.

Young Tom figured why not cut out the middleman and put some of that cash in his pockets.  To do that he had to raise himself up a notch and compete with the old boy Kentucky breeders like Leslie Combs and Warner Jones. First, he mastered the science of bloodlines and injected his own maverick thinking. Then he went to the banks, borrowed up to his chinstrap and by 1980 the 600-acre Tom Gentry Farm out on the Paris Pike was a million dollar a year operation with upwards of 100 mares and foals running about.  I’m sure stories about his rise and eventual fall are still legend in the Lexington breeding sheds.

Tom’s troubles started in 1986 during divorce proceedings that made the local gossip columns.  The banks panicked and rushed to call his loans, as did his other creditors, forcing him into bankruptcy.  He lost his farm and his bloodstock and had to file “Chapter 11.”  After a long battle with federal authorities he was convicted in 1993 of, among other things, hiding assets and sent to a federal prison downstate.  He nicknamed it “camp.”  But the feds were after bigger fish and released him after five months for providing testimony in another case.  He told me that the night before he went away he dressed up in prison stripes, went to his local watering hole and bought drinks for his friends until the next morning when the federal marshals came to pick him up – classic Gentry.   Those who lost money probably didn’t see the humor.

I first got to know Tom in the 1970s, when another CBS colleague, Heywood Hale Broun, introduced us during Derby week.  Gentry had been admiring Woodie’s choice of rather loud patchwork  jackets and pretty soon he was dressing in either multiblock jackets or pants himself.  Thank god he didn’t always choose to wear them both at the same time. Not too often anyway.   Even his racing silks reflected his sartorial splash – yellow, with blue and yellow blocks.

Sale brochure from 1985

Tom hadn’t sold his first million-dollar yearling yet, but you could tell right away that was the goal.  I checked out Gentry’s bonafides with another mutual friend, Churchill Downs race caller Chic Anderson, and he said something like, “I’d keep an eye on Tom if I were you.”

That summer we got together, all of us and our wives, at Saratoga for cocktails after the races.  Now with storytellers the likes of Broun and Gentry, suddenly the hour was approaching ten and we hadn’t yet thought about dinner reservations.  Tommy said, “Let’s just drive out to Siro’s,” an upscale Italian restaurant of note, “and show up.”  The parking lot was empty when we got there, the place was dark and there was no sign of life.   Gentry jumped out of the car and disappeared through the front door. Seconds later the lights came on and the place came alive.  “What just happened?” I asked Tom  “Well, Bud,” he said with a wry smile, “I handed the chef a thousand cash and told him to bring on the food.”

It wasn’t long after that Gentry became the toast of Lexington, with his elaborate parties during the Keeneland sales featuring helicopter rides and elephants and the likes of Bob Hope as entertainment. When a certain Lexington hotel couldn’t provide Hope the right accommodations, Tom had them rip down the walls and make a suitable suite for America’s star comedian.   Oh, and I believe his house guest for that year’s Derby was former President Jimmy Carter. His investors would foot the bills for all of this, of course.  They were just happy to be along for the ride.

The annual sales party at the Tom Gentry Farm became legendary in the 1980s

Tommy’s ingenuity had no bounds.  He cornered Woodie one day and said something like, “Heywood, you know a lot about language and bloodlines.  Can you help me suggest names for these yearlings that are being groomed for the sales?  It might  get the bidders just a little more excited.”  I don’t remember the exact results of that joint enterprise.  I do remember some unique names being mentioned late into a long evening, some of them unprintable.  And I can tell you that the best example of Woodie’s naming technique was a Thoroughbred he later owned.  She was by Runaway Groom out of Duty Free.  He named her Careless Heiress.

It was in 1979 that Gentry scored his life-changing coup.  At the then annual July yearling sales at Keeneland he brought the full load of freebies to his trailer where prospective buyers milled about.  There were Tom Gentry wristwatches, Tom Gentry walking sticks and pens and pencils –  and matchbooks with the prospective customer’s names printed on them right below the  Gentry name – and julep cups filled with the real thing,  and on and on.  And the customers came and came to inspect the Gentry yearlings – and pick up a few souvenirs.

Gentry, in trademark patchwork pants at the Keeneland July Sale

A contingent of buyers had just arrived from Asia, fresh money that Gentry paid proper attention to.  Figuring that the good old boy breeders had the Eastern establishment buyers pretty well locked up, he was always looking around.  That’s why he bought a place near Santa Anita.  And he was among the first of the eastern breeders to discover Del Mar for his racing operation.   Full disclosure:  Woodie and I owned a small piece of a Round Table filly named Wedding Reception with Gentry.  She broke her maiden at Del Mar in those blue and yellow blocks.

At a party on the night before the 1979 sales, Tom was entertaining a Japanese investor, Kazuo Nakamura, who had shown considerable interest in a Hoist the Flag colt, Gentry’s star entry.  Decked out in his loudest patchwork sport coat, Tom took Mrs. Nakamura, an attractive, slightly-built woman, for a spin around the dance floor. You couldn’t help but notice. The prospective buyers beamed.

When the bidding started the next day, Gentry was hoping for maybe half a million for his star colt.  But the Japanese contingent had come to play.  When the hammer finally came down, Mr Nakamura won the day with a $1.6-million bid, a record at the time for yearlings and Tommy”s first million-dollar sale.  He jumped out of his chair, ran over to Nakamura and draped him in his best patchwork.

“The coat is yours,” cried Gentry, “and the souvenirs in the trailer, take what you want.”  I asked him later how that went.  “Well Bud,” he said, “ when I went back to the trailer, the only things left were the air conditioners.”

E.S “Bud” Lamoreaux III is a creator and former executive producer of CBS News Sunday Morning with Charles Kuralt.  He won four Eclipse Awards for national television excellence.

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