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#3- Life Lessons From Charlie LoPresti

"I probably miss a little bit by not being in Florida in February and March, but you know what, I’m not that consumed with winning the Kentucky Derby.”
#3- Life Lessons From Charlie LoPresti

In April 2021, Charlie LoPresti quietly retired from racing. If I had to name my favorite trainers in the world of horse racing, Charlie LoPresti would be in my top three. He's best known for training two-time Horse of the Year Wise Dan. He's a true horseman, who prided himself in running a small stable and operating like the trainers of years past. A few years ago, Ryan Holiday's book "Ego Is The Enemy" made the rounds among the movers and shakers in Silicon Valley. It even infiltrated the offices of many NFL and college football head coaches. In this short post, I want to talk about Holiday's chapter called, “What’s Important to You?” I doubt Charlie LoPresti read the book. But in a world of achievement and ego, LoPresti might be one of the best examples of someone who long ago mastered his ego and decided what was important to him.

Even after training a two-time Horse of the Year and after winning a Breeders’ Cup, Charlie LoPresti continued to conduct business like the trainers of old. He took out his trainer’s license in 1993, maintained a relatively small number of horses, and developed a reputation for taking his time with his prospects. Another horseman once said of LoPresti, “He is a horseman in the truest sense. He gives them the time they need and does everything the right way.” Charlie LoPresti’s biography on the NTRA website reads, “Unlike most major trainers who relocate to various tracks throughout the year, LoPresti is based year-round at Keeneland Race Course in Lexington, KY.”

“This is just what works for me,” said LoPresti, whose refusal to travel away from Keeneland and his nearby farm during the winter months set him apart from his more prominent national colleagues. “The farm is 365 days a year,” he said, “and besides, I just feel like I can do a better job staying here.” Later he said, “I know the economics of the game means that most trainers need to keep racing, but we like to give the horses a little break, just like horsemen used to do it years ago.”

In Ryan Holiday’s book, my favorite chapter compares the lives of Ulysses S. Grant and his friend William Tecumseh Sherman. They were dual architects of the Union’s victory and were two of the most respected and important men in America. But following the Civil War the two men took different paths. Grant went on to be a colossal failure as President and went bankrupt as a businessman and investor. Meanwhile, Sherman repeatedly declined offers to run for office. “I have all the rank I want,” he told them. As Holiday writes, “Having seemingly mastered his ego, he would later retire to New York City, where he lived in what was, by all appearances, happiness and contentment.”

For Charlie LoPresti, having a huge barn like the Todd Pletchers and the Steve Asmussens was never important to him. “I just feel like I can do a better job seeing them all myself every day, not that the big guys don’t do a good job,” LoPresti said. “For some people, that works for them, but I’d be overwhelmed if I had 100 horses.”

When Charlie LoPresti trained horses, he intentionally didn't race year-round. He didn't want to move his stable from track to track. “Strategies are often mutually exclusive,” Holiday writes. “One cannot be an opera singer and a teen pop idol at the same time. Life requires those trade-offs.” The trade off for LoPresti might have been not winning a Triple Crown race. But he mastered his ego long ago and enjoyed doing things the way he wanted to do them. “I just want to be more like the old, tiny stables,” he said in a New York Times article years ago. “If you look at the Mack Millers and Frank Whiteleys, they didn’t run 365 days a year. A lot of people can’t stand still for that, but … the people need time, and the horses need time.”

Most of Ryan Holiday's books have a philosophical bent, and in this short chapter he encouraged the reader to sit down and think about what’s truly important and then take steps to forsake the rest. LoPresti seemed to master this, while Grant struggled. A Ponzi scheme left Grant publicly bankrupted after a failed presidency. Sherman wrote with sympathy and understanding that his friend Grant had "aimed to rival millionaires, who would have given their all to have won any of his battles." Ryan Holiday writes that Grant couldn't decide what was important- what actually mattered- to him.

We are an achievement-oriented society. Too many times we get locked into climbing to the next level, buying the bigger home, looking for the next job, striving to make partner. Holiday writes, "So we unconsciouosly pick up the pace to keep up with others. But what if different people are running for different reasons? What if there is more than one racing going on?"

Only you know the race you are running. For all those years as a highly successful trainer, Charlie LoPresti knew the race he was running. “I don’t want to run horses 365 days a year,” he said. “I want to run them when I think the best racing is, and I think the best racing is spring, summer and the fall. I probably miss a little bit by not being in Florida in February and March, but you know what, I’m not that consumed with winning the Kentucky Derby.”

Robert Louis Stevenson said, “To know what you like is the beginning of wisdom and of old age.” LoPresti is a wise horseman who liked his small stable. And he knew what was important to him- operating his stable like the old time trainers, giving his horses the winter off, and basing pretty much his whole operation out of Keeneland and his Forest Lane Farm in Kentucky. In a world that is consumed with winning the Kentucky Derby, Charlie LoPresti mastered his ego, ran his own race, and will forever be remembered as a true horseman.