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Power Broker: Joan Pletcher, Todd’s Stepmother, Rules The Horse Mansion Realm

'saratoga living' sits down with the family matriarch to discuss the real estate business, her Southern upbringing and more.

Joan Pletcher
(from left) Joan Pletcher, with husband J.J. (center) and stepson Todd (right). (Susie Raisher)

As a military brat—a sort of national emigrant, born into a life of packing up and moving every year or two—I’m not used to standing still for very long. After college, it was what drew me to anchor myself in New York City, where the pace and energy match my distinctly itinerant, if not urban, mindset. To this day, as I navigate the city’s immense grid, I find it easy sport to tell the tourists from the natives by who’s standing still on the sidewalk. So when I was invited to venture to Saratoga Springs for a couple of days to interview Florida-based real estate powerhouse Joan Pletcher—stepmother to one of Saratoga Race Course’s most oft-winning trainers, Todd Pletcher—I paused, at first. After nearly 40 years in Manhattan, I’d never been to the Spa City. Not even during the four years my nephew was enrolled at Skidmore College, bad uncle that I am. So, “Why not give Saratoga Springs a visit?” I thought. It was perhaps better to be invited to Saratoga for the first time during the heat of summer’s racing season, as I was, than the notoriously harsh winters that only invite shoveling. And it was only 186 miles from my TriBeCa apartment along Amtrak’s scenic Hudson line. Further, while Saratoga might lack the coveted “C” after the “NY” in its postal acronym—a monogram I’ve come to revere more than my own—I’d heard the food scene was great. Count me in, I said.

Arriving at the deceptively nondescript Saratoga train station, I’m driven through the town proper, past a smattering of National Velvet-worthy emerald green horse farms framed by white picket fences, to a sprawling subdivision, replete with gorgeous homes in every architectural style and their meticulous landscaping, the abundant and fully crowned trees betraying the nouveau, only riche.

“We don’t use the front entrance,” says the Champagne-haired Joan Pletcher, stylish in jeans, blue-and-white silk equine-themed Hermès blouse, Gucci belt and (she’s clearly at home) Croc slip-ons as she opens the considerable wooden door. Somewhat intimidated by the stately manor it was affixed to, I immediately exhale as I pick up on her mannerly Southern accent and make my way inside. “You just missed everyone,” she tells me—everyone being her husband, stepson and grandkids. “They’ve been over here, and I’ve been making potato soup, grilled cheese sandwiches and potato chips.” Comfort food, I think, and I remember to relax.

The Golden Legacy Training Center, one of real estate giant Joan Pletcher’s property listings, is 114 acres with five barns and is listed at $3.75 million.

I say “remember” because, in another lifetime, when I was cast in my first professional play as an aspiring young actor, I was so starstruck by the Broadway veteran playing Hamlet that I was always a nervous wreck around him. One day during rehearsal, I happened upon him while he was standing outside the theater and I timidly said hello. Without a word, he took out a pack of Marlboros and a matchbook, lit his cigarette, tossed the match, handed me the matchbook and walked away. “Did I do something wrong?” wafted through my brain like his trail of cigarette smoke through my lungs. I looked at the matchbook and there, designed as if for a chic restaurant or hotel bar, were the words “Actors Are Just Folks” emblazoned on its cover.

Joan is just folks. Despite being the female lead to a trio of male equestrian stars—her husband, Jake “J.J.” Pletcher, is an acclaimed Thoroughbred trainer, and her stepson, Todd, a two-time Kentucky Derby winner and recipient of seven Eclipse Awards (horse racing’s Oscars) for Outstanding Trainer, both with millions of dollars in purse earnings—Joan is refreshingly unassuming, unlike, say, a number of A-list actors I’ve encountered. “Born and raised in Little Rock,” she tells me as I’m invited to sit on the sofa and she reclines in a La-Z-Boy an arm’s length away. Her native cordiality neatly camouflages her reputation as a real estate powerbroker, traversing between Saratoga, where the extended Pletcher family resides during the racing season, and her home base, in Ocala, FL.

“I grew up around construction,” Joan says, seamlessly expanding on her Arkansas roots. “My father was a builder and developer. He bought 200 acres and built our house, along with other houses on the property. And when people got close, he’d buy another 200 acres and do the same thing.” She was part of the construction crew at a very young age, she reflects. “I’d go to work with my father from age three, and the guys would carry me around. When I was five, he bought me my first horse, and that’s when I started riding. I’d get up at five in the morning to clean the stalls, and then catch the seven o’clock school bus. I still think about it, because so much of what I do now is what I’ve grown up doing.”

Joan Pletcher (center) enjoys a conversation with her daughter-in-law, Tracy (left) and granddaughter, Hannah.

After such a robust childhood, Joan admits to facing her first real crossroads when she lost her first husband to leukemia. “I’d spent seven months sleeping in a recliner and cooking on a Munsey Toaster,” she says, pausing to grab a tissue “for an eye allergy,” she explains. Joan’s innate spirituality reveals itself. “I had given myself a year to get back on my feet. And I said, ‘God, I don’t know what you’ve got planned for me, but whatever it is, I’ll do it. I’m in no hurry to meet anyone or do anything, but if it’s possible, I’d like to meet somebody that I’ve got a lot in common with.”

And that she did. Jake Pletcher—“J.J.” as he’s known, or “Pletch,” as Joan alternately calls him—had been working for former Detroit Lions All-Pro and businessman, Cloyce Box. After retiring from the National Football League, Box found considerable success in the oil and gas business in Texas—and, in a Hollywood footnote, as the owner of the original Southfork Ranch from the TV series Dallas. After J.J. went out on his own, he and Box remained partners on horses, and Joan met J.J. at the racetrack. “J.J. was in his box studying the tote board. And I said, ‘I don’t know who that is, but I’d like to meet him.’ And when I shook his hand it was like electricity. We’ve been together ever since.”  Thirty-eight years, to be exact.

It was Box who later persuaded J.J. and Joan to move to Ocala, where he wanted to build an equestrian training center. “Cloyce said to J.J., ‘If I buy this property, will you and Joan go to Ocala and build us a training center?’” Joan tells me. “Well, J.J. and I were ready to give up the gypsy life of moving from Kentucky to Chicago to Louisiana and back to Arkansas. And Cloyce said, all you have to do is bring your toothbrush, and he’d build a house wherever we wanted it. And he did, and that’s what brought us to Ocala.” Once again, Joan found herself back on a construction crew (though something tells me she was both captain and crew). “Pletch would handle the horses, and I oversaw the construction of the house and all the landscaping. It looked like a miniature Tara. We lived in that paradise and ran the property for 12 years.” And paradise was where they stayed.

Joan Pletcher
This $8.375 million exquisite French chateau estate sits on 91 acres just minutes from World Equestrian Center Ocala.

“Ocala. Luxurious Country Living.” That’s the title of Joan’s real estate portfolio of Ocala offerings. Thumbing through the catalogue, I find listings titled, “Masterpiece Manor,” “Historic Charm” and even a “French Château Equestrian Estate,” among the other “move-in ready” farms for horses and cattle. Given the obsession New Yorkers have with real estate, I’ve met a number of “celebrity realtors” over the years who, by the very nature of their profession—how shall I put it?—embellish a lot when it comes to selling a property. But unlike the luxury condos that make record-breaking headlines on “Billionaire’s Row” in Midtown Manhattan, people actually live in the properties Joan lists. And while licensed only as a Realtor, she prides herself on being a psychologist as well, in terms of what motivates clients to buy or sell.

“My biggest concern is always being the kind of person I need to be for my clients,” Joan confides. “I don’t want to say or do anything that would have them make the wrong choice in their life. Before I list a property, I talk to clients about what they want, what their dreams are, what they would do if they sell. While I’ve been told I have the patience of Job, it takes time for people to make up their minds. But God’s given me a sixth sense of what someone really likes, even though they may not tell me. I can pick out six houses, but I can tell you which one they’ll end up with.”

I remark that I often see the same people in New York’s ultra-affluent Hamptons as I do in Manhattan. The accoutrements are perhaps more casual, but I’ve seen the words “price upon request” applied nearly as often in the village of East Hampton as on Madison Avenue. I ask Joan about Ocala vs. Saratoga: Is there much difference among her clients? Does she have to change gears? “I’ve seen Ocala grow from when we went there in ’85, and it was a very quiet town,” she ruminates as she shifts in the recliner. “It’s totally different from South Florida. We’ve got the rolling hills, the live oak trees, the Spanish moss.” She elaborates on the city’s diversity—in soil, that is—noting the abundance of water and aquifers, as well as limestone, “like Lexington, really good for horses,” she says. She comes around to Ocala’s growing diversity in people, too. “We have a mix of different nationalities. Most of the people are down-to-earth, and while we’ve got a lot of quiet wealth, a lot of people don’t even realize that we have that. I see many of the same people in Saratoga as I see in Ocala. So it doesn’t really feel like I have to change gears. I feel like I can just be me.”

Speaking of switching gears, I note that Florida is many things, but it’s also the state with the highest percentage of its population older than 65. “Do you and J.J. ever think about retiring?” I ask. “No,” she says without hesitation, “I want to do it all. I don’t think it’s ever over. I’ve got two speeds, either stop or full speed ahead.” A moment later she meditatively adds, “I feel like I’m cheating J.J., because I’m so busy. I do think I want to slow down and spend more time with him and all… ” she reflects, her voice trailing with its Southern inflection leading to a modest admission: “When the bottom fell out of the oil market and the horse business slowed, we kind of retired for a little bit. We taught each other golf,” she says. “We’d play seven days a week, 36 holes on weekends. We won the husband and wife championship at Black Diamond Ranch in Lecanto, FL, and I won the club championship twice.”

This $6.675 million luxury estate and equestrian farm has a 7375-square-foot residence and a 10-stall stable.

Real estate power broker. Equestrian authority. Self-taught golf champion. As she’s talking I begin to pick up on a familiar theme. “When the economy picked back up,” she continues, “we started getting back in the horse business, full steam ahead, and I quit playing golf because you can’t play golf and be successful in real estate.” The late Arnold Palmer might disagree, but I get her point; she has a laser-like career focus. “Now I’ll go out and play maybe once a year, a tournament or benefit.”

Yes, yes, but I can’t help but wonder, what is it that clearly propels Joan’s success like a titanium driver on a par-5? Joan Pletcher is a perfectionist! That’s it! I know that song by heart, and I can’t resist asking: “Joan, are you a Virgo, by any chance?” She is. (As you may have suspected by now, I am too.) Our birthdays are one day apart. We both high five and commiserate on what I consider a curse: having to do things a particular way and the constant pursuit of improvement.

“My mother taught me, if there was a will, there was a way,” she says, adding the equally epigrammatic, “and my father taught me, if it was worth doing, it was worth doing right the first time. That’s probably why I’m a perfectionist. I don’t want to do things two or three times. It probably takes me longer than if I do them halfway and move on, but I just can’t do that.” Ditto, I say, as I glance at my watch and note that it’s time for me to head out to meet my saratoga living colleagues. Thanking Joan for an enjoyable afternoon, I reach over to pick up my cell phone where I left it on the coffee table, pausing as I notice two lone items resting there: the current issue of Forbes and an open paperback, Danielle Steel’s Fairytale. Perfection again. A set designer couldn’t prop it better.

The next day, I run into Joan in her box at Saratoga Race Course, as Todd has a horse in an upcoming race. It’s my first time at the venerable racetrack—any racetrack, for that matter. Joan and I chat for a while and, returning to join my colleagues, I glance back at her, looking very regal in her black lace dress offset by her shimmering hair. I suddenly think of the royals and their horses, how Queen Elizabeth, the epitome of regal equestrians, attended the 2007 Kentucky Derby, and what it must have been like to be there for that “Run for the Roses.” Then it occurs to me—I was just in the company of “royalty,” though, as Americans, we eschew that status. That said, the British monarch does recognize the good work of foreign nationals with an MBE, OBE and CBE, as part of her New Year’s Honours and, in June, to commemorate her birthday.

And, so, with Her Majesty’s permission, I’d like to hereby nominate Mrs. Joan Pletcher for a CEE, that’s “Commander of the Equestrian Empire” for you non-royals, for her grit, grace and exceptional achievements.

Dame Joan! It has a winning ring to it, don’t you think?

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