Remembering Legendary Hamburg Horseman, Preston Madden 


Hamburg has lost our legendary neighbor, retired horseman and developer Preston Madden, who has died at the age he would probably describe as “none of your business.” He told us many times he was not a fan of news outlets who were so quick to identify the age of the deceased. “What does that matter?” he pointed out with a wry smile when explaining to us in 2018 that his wife Anita would not have appreciated that being the first item reported in the news of her death. She was “so much more than that,” he said. And so was he.

The late Anita Madden (Photo provided)

Madden’s office on Sir Barton boasted the most comprehensive archive of the Hamburg Journal outside of our own, and he sat down for many interviews with us over the past two decades, most recently for a summer 2018 cover story, and again after the death of his wife of 62 years, Anita, later that fall.  Although he had been recently hospitalized and released, he died at his home in Hamburg on May 5. 

At the time of his death, Madden hadn’t been to the Derby in three decades, but always followed it from afar. The Derby was postponed only twice in his lifetime. The first was in 1945 due to World War II, and the second was this past weekend, when the Run for the Roses was rescheduled for Labor Day weekend due to COVID-19.  

The Derby shaped his life and legacy. “Alysheba made my life,” he once told us of the 1987 Derby winner.


Hamburg, champion two-year old of 1897, from the book “The Wizard of The Turf, John E. Madden for Hamburg Place” by Kent Hollingsworth

Preston Madden was heir to one of the most prominent families of horse racing. His grandfather John E. Madden bought the yearling, Hamburg, for $1,200 in 1896. He parlayed Hamburg’s winnings and sale into the purchase of the farm and breeding operation that would become Hamburg Place along Winchester Road.

The first Triple Crown winner, Sir Barton, was bred at Hamburg Place. So were four more Derby winners, and four Belmont Stakes winners. Today, Sir Barton Way is the primary Hamburg artery between Winchester Road and Man o’ War.  

“Money is only the symbol of success — not to be confused with success itself.”

Breeding five Kentucky Derby winners, five Belmont Stakes winners and the first Triple Crown winner, John E. Madden’s legacy was set, but not complete. It was his grandson, Preston Madden, who went on to win big at the races and even bigger in real estate.  But, he told us in a 2018 interview, “Money is only the symbol of success — not to be confused with success itself.”

Preston Madden
Preston Madden (photo provided)

He explained, “Before this end of the farm was developed, I was extremely busy breeding horses. I had 100 horses on the farm, so my son [Patrick] did the actual [Hamburg] development and my wife, Anita, named the streets. I think she did a hell of a job. My grandfather bred over 100 stakes winners. She had a list of 100-plus stakes winners —Sir Barton, first Triple Crown winner, and Alysheba were the obvious choices so she took from all of his stakes winners and my stakes winners.”


The Maddens transformed Hamburg Place into the thriving commercial corridor that it is today, but Preston always knew he still wanted to carry on the family tradition. Even in grade school, he told his classmates that he wanted to breed a Kentucky Derby winner.

Wanting desperately to bring back the garland of roses, a feat that Hamburg Place had not experienced since Flying Ebony won the Derby in 1925, Preston took his chances with Vegas Vic in 1971 and Kentuckian in 1972. Vegas Vic finished sixth, Kentuckian finished 10th. And then came Alysheba.

“Alysheba made my life,” Preston said.

(Photo provided)

Preston had bred Alysheba and sold him as a yearling to Dorothy and Pam Scharbauer for $500,000. And in 1987, Preston would get his third chance at a Derby winner when Alysheba walked into the starting gate at Churchill Downs.

At the top of the stretch, Alysheba’s legs buckled after colliding with Bet Twice and it looked like Preston’s quest would end in disappointment yet again. But Alysheba and jockey Chris McCarron recovered and made a last ditch run for the finish, edging out Bet Twice for the win. Preston and Anita, watching the race from a balcony overlooking the track, were riveted.

“My wife was on my right. It became clear before the finish line that Alysheba was going to win,” Preston said. “This is the third time we’ve run in the Derby and I had been trying to win this race all my life, so when people ask me what were my thoughts when he crossed the finish line, I tell them the true story. One hundred yards out, my wife took her left arm and put it around my neck and pulled my head down” and planted such a kiss on him that he could barely even see the finish line. The memory brought a smile to his face during the interview (even if the kiss briefly obscured his view).

After exiting the Winners’ Circle, the Maddens were in the Director’s Room when a girl who attended grade school with Preston walked in and proclaimed, “I want everyone in here to know that when we were in the third grade,  Preston Madden told me he was going to be a Kentucky Derby winner.”

“You think my wife was happy because [this classmate] remembered me? Hell no, she didn’t like it at all,” he told us in his summer interview, laughing at the memory.


Madden maintained an office on Sir Barton well into his 80s and was always happy to tell guests the story behind every image on the walls — Sir Barton, Old Rosebud, Man o’ War, Hamburg, and Pink Pigeon are just a few of the familiar names pictured in paintings and photographs.

Between the gallery of fine art, the burnished wood, and the open bar, his office felt classic and reminiscent of an episode of Mad Men, if Don Draper were a horse racing legend.

The painting centered over the receptionist’s desk and illuminated by lamps that serve as spotlights—a painting of Alysheba winning the Kentucky Derby under the Twin Spires.

That moment was everything to him. 

Madden retained the legacy and memory he built both in Hamburg and in horse racing.  It’s been more than two decades since an epic Anita Madden Derby Party was hosted in Hamburg, but no one has forgotten. It was Preston who suggested one year’s theme, “The Diamond As Big As The Ritz,” an homage to the fact that one of F. Scott Fitzgerald’s Princeton classmates was Madden’s father.

“I’ve been lucky as hell,” he said in his cover story interview with HJ,  “and I think it’s important to understand that luck is a big factor, particularly in the horse business.”

He reflected at the time, “There were expectations for me to do things and I was lucky enough to be able to accomplish those, but the year that Alysheba was foaled, there were roughly 36,000 registered foals, but how many Kentucky Derby winners are there? I’ve been lucky and God’s been good to me and I’ve had some fun and I’m going to have some more fun.” 

And he did. 

Hamburg mourns his loss.

Milward Funeral Home is handling arrangements, and has announced that a celebration of life may be held at a later date. In lieu of flowers memorial contributions may be made to Bluegrass Boys’ Ranch, P.O. Box 12128, Lexington, Kentucky 40580.



This article also appears on page 10 of the June 2019 print edition of Hamburg Journal.

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