An atypical timeline: Get to know Diane Naylor
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She stands behind her man (because, sometimes, she has to), but this former Southern belle was, and is, a power player in her own right
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You no doubt know her husband, Irv. The six-time National Steeplechase Association champion owner’s story has been told and re-told. But you might not know the story of Diane Naylor, the potent force behind the duo’s continuing success, and the one her husband credits for his daily motivation.
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Theirs is a modern love story, one that ironically began with “Love Story.” Like the 1970 movie classic, the relationship grew from pure affinity and mutual respect. Irv and Diane Naylors’ life together has been punctuated with business success, propped up by their still-growing extended family and bolstered by the easy friendship that springs from 46 years of marriage.
There’s affection, adoration and a measurable still-simmering sexual tension and innuendo driving the dynamic partnership some 50 years after their first, star-struck meeting.
Trace Diane Naylor’s timeline to understand how this former tomboy found herself a young female executive in the business world in the late 1960s – a time slightly unusual for a woman of any age. Hear how a handsome business owner overcame her initial skepticism to capture her heart.
From frog-gigging in rural Virginia wetlands to supping with England’s Prime Minister, from a fateful day at Maryland’s Grand National to helping Irv accept each of his three three Eclipse Awards, Diane Naylor’s life has been accented in equal measure with tears, fears and cheers.
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1940s – The importance of family.
Diane Gregory was an only child, growing up in Richmond as part of the Baby Boom generation.
“I always felt I had two sets of parents,” she says. “My parents and grandparents lived together, so I had the influence of my parents – William Bingham Gregory and Joan Council, plus my grandparents K.K. Council and Elizabeth Wells. They’d formerly (lived in) Council, North Carolina.
“When I asked my father about our lineage, he said we came from a great group of horse thieves. Needless to say, I grew up with lots of humor.”
Diane spent the school year in Richmond, the summers at her grandparents’ farm on the Rappahannock River in Lively, Virginia. She embraced country life, though she did curtly rename Lively “Deadly, Virginia” when she was a teen, Diane says, for lack of social options.
She did “the usual things” through high school — 12 years of ballet (“a career thought,” flute in the school orchestra, tennis lessons, voice (“I flunked,”) and cotillion.
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But in summer, Diane embraced the tomboy. “No more school dresses, yay! I excelled in tree climbing, shooting, fishing, rowing, sailing and frog-gigging.” She took flying, riding and ski lessons. In short, she majored in electives that expanded her world view, both the macro and the micro.
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1950s – Her grandfather wrote the book (figuratively speaking) on ‘How to control a child.’
Born in the 1880s, her grandfather was a real, old-fashioned “gentleman,” Diane recalls. “Just wonderful. His own father was a great poet, and my grandfather (carried forward) that imagination.
“I spent all my childhood summers at the river with him, and there were so many animals, especially rabbits, running around everywhere.
“He basically wrote the book – ‘How you control a child.’ So I’m down there, and we’re playing with the rabbits. My grandfather tells me ‘the rabbits are going to send you a letter,’ and I think that’s the greatest thing, ever. My father – he was a beautiful craftsman – built me a rabbit mailbox and tacked it to a tree, just at my height to open to get my mail.
“I’d run out every morning and there’d be a letter in there from Buster Rabbit. I’m too young to read it, of course, so I’d run back by my grandfather.
“He’d read it to me. He’d written it, of course.
“So, instead of them fussing at me and telling me what to do all day – which they would have had to – he’d write things from the rabbit’s point of view. Like, it’d say ‘yesterday you were swinging too high in that swing. You know you should’ve been taking a nap how your grandmother said.’ And of course I’d want to do exactly what the rabbit said because I wanted to do right by the rabbits.
“I wish I’d saved every one of those letters. It was magical.” And, Diane adds, it worked.
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1960s – Business sense instilled early.
Diane’s parents started a wholesale and retail leather goods business with her grandfather, branching out into an arts and crafts shop and a year-round Christmas shop. “I really liked the business world,” she recalls. “I loved to watch it grow.”
Since her mother was suffering from rheumatoid arthritis after she got out of college, Diane went to work for the family business. She was in charge of staffing, setting up and buying for 10 leased Miller & Rhoads department store shops in Virginia and North Carolina. “I loved every minute of it.”
In between, she wedged in more tomboy activities – flying, riding and ski lessons. “Somewhere in there was a very short marriage — nine months, when nine days would have sufficed,” she shrugs. “It was a lovely, formal affair. My father said ‘well, at least it was paid off’ before it ended.”
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1970 – She wasn’t buying the handsome business owner’s line, literally or figuratively.
Young business executive Diane Gregory met packing business owner Irv Naylor, 13 years her elder, at a 1970 trade show in Chicago. His company, Lok-Box, had a craft division, one that neatly meshed with Diane’s family shops back east.
“I was there to buy,” she recalls. “But I wasn’t buying Irv’s line.
“Not his line. Nor his lines.”
Still, she said yes to a date. It was classic dinner-and-a-movie; ironically, they went to see the three-handkerchief tearjerker, “
Love Story,” about the tragic loss of a lifetime love. “Love means never having to say you’re sorry,” was the Ali Macgraw catch phrase that persists even today.
“So I’m bawling through the whole thing,” Diane recalls the exact night. “Right at the end, I glance over at Irv. Maybe I detect a glint of a tear in his eye, and I’m thinking ‘there may be hope for this man.’
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Diane and Irv Naylor in May 2016.
Tod Marks
photo
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Just the facts:
Diane Naylor
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Nee Diane Gregory, graduated high school in Richmond in 1968, and from Virginia Commonwealth University in 1971
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Married Irv Naylor in July, 1974
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President of York, Pennsylvania Planned Parenthood in 1983, president of
York Junior League
1988-1989
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Brought the world’s power players to a speaker series for the York Junior League – Margaret Thatcher, Willard Scott, the princess of Jordan, Joan Rivers
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1974 – The many facets of marriage.
Diane continued her tennis and skiing lessons – Irv had by this point started the
Ski Roundtop resort in Pennsylvania. “Cooking and entertaining became a big part of my life,” she says of her entree into executive spouse duty.
“Irv had built an indoor tennis and racquetball facility – and, lucky me, I became manager. There were more new skills to learn – how not to double book courts, how to avoid a defective alarm and going in at 2 a.m. to fix it, how to throw a lobster party for 150 people.
“I learned what the inside of a men’s locker room looks like and how to tidy it up. I learned what chemicals are needed in the swimming pool and how much food do you order for the snack bar, how to repair a hole on the outdoor courts.
“I was very happy when he sold it.
“So much for a lady of leisure.”
One of the highlights, Diane recalls, was meeting the man responsible for making condoms available in Thailand.
“I made the local newspaper by being in a condom blowing contest.”
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While president of the York Junior League Naylor suggested a speaker's series as a fundraiser. British Prime Minister Margaret Thatcher was one of the speakers. Photo courtesy of Diane Naylor
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‘Never much of a rider, but I liked the clothes.’
When she was a teen, Diane says her “parents were concerned I was spending too much time in the business and that I needed to broaden my horizons. One Christmas, I was presented with the riding attire and a gift certificate for riding lessons. My only riding experience had been sitting on a pony the gypsies brought to our neighborhood.
“I liked the clothes, and enjoyed the riding lessons at Deep Run Hunt Club (near Richmond), but I was not keen on horse grooming and hoof picking. My idea of riding was to appear, have the horse ready, and hand him to somebody else when done.
“I suppose I watched too many movies.
“When Irv and I were first married, he thought he would assess my skills, so he puts me on his horse Walking Jet. I ask you, do you think there was something in the name?
“Of course I was run off with.
“I (joined) a trip Irv organized for family and friends with Willie Leahy along the Connamara coast in Ireland. The riding I loved, but you had to find your (own) horse in the morning. Fortunately, his two grandchildren took pity on me and found my horse and saddled it up.
“Our next riding trip was more my style, in Spain. One day we set out to ride, and it really began raining. Naturally, the Spanish did the only civilized thing – we rode into town, found a good restaurant and stayed there all day to eat and drink.”
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Mason-Dixon line as an actual boundary.
“When I moved from York to Reisterstown, Maryland, my parents hoped by moving closer to Virginia, my southern accent would reappear. ‘You talk like a damn Yankee’ was a phrase I heard more than once.”
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The quotable
Diane Naylor:
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“One of my favorites: ‘Don't confuse my personality with my attitude. My personality is who I am. My attitude depends on who
you
are’.”
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“I’m a great lover of Winnie The Pooh, and this is the best A.A. Milne quote – ‘If you live to be a hundred, I want to be a hundred minus one day so I never have to live without you’. I gave Irv that on a little paperweight. I think it describes us perfectly.”
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Her favorite gem from the stacks of cards that arrived to her husband’s hospital room every day after the April, 1999 fall: “Do you ever think your Guardian Angel went out for a smoke?”
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The Naylors' 2019 Christmas card, courtesy of Diane
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They’d purchased the farm north of Baltimore years before, but only moved there five years ago after retrofitting the farmhouse. “We both truly love being here,” Diane says. Farm trainer Cyril Murphy says the Naylors can watch horses in the big turnout pasture from the back patio, and watch the crew swimming horses for fitness in the arm pond from the front porch. “It’s a great setup,” Murphy says.
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April 17, 1999 – The first day of the rest of their lives.
“Yes, I am crying as I think about it, even now,” Diane says. “If someone were to ask what is the worst fate other than death, you know what (any athlete) would say – becoming a quadriplegic. For someone whose entire life was so physical, what happened was tragic."
Irv Naylor’s interest in jump racing had stemmed from foxhunting. He was joint-master of Pennsylvania’s
Rose Tree Hunt, and he rode point-to-points on his “fastest” foxhunters to start with, then shifted focus to the NSA circuit. The then-63-year-old had the Maryland Hunt Cup (it would have been his fifth try) in sight in 1999 when disaster struck in the Grand National timber stake.
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Irv Naylor and Emerald Action before the start of the 1999 Grand National. In 1996 the horse had won a Novice timber race at the Elkridge-Harford Pt to Pt, an allowance timber race at the Grand National meet and had finished second in an allowance timber race at Willowdale, all with Irv in the irons. Jack Fisher was the trainer.
Douglas Lees photo
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Diane recalls the fall that changed it all. “I was up on a scissor-tail, high in the air with other owners to view the race,” Diane says of the hard spill at the second-last. “He’d promised me this was his next to last race, though he kept assuring me that foxhunting was far more dangerous, and if you fell in the middle of nowhere, it wasn’t like a race meet with readily available medical help.
“They had to wait ’til the race was over to lower the scissor-tail. This was one of the longest moments in my life – I wanted to be at his side.
“Irv was flown to shock trauma. I was so thankful Dr. Phoebe Fisher was allowed fly with him and held his hand the whole way. Her husband, Dr. Rush Fisher, joined us at the hospital and helped me understand the implications” of the fractures of the C5 and C6 vertebrae that were likely to leave him fully paralyzed.
“When I was finally allowed to see Irv, of course his main concern was about the horse, though he was also wondering what happened to his tack and why did they have to cut his riding boots.
“I was at the hospital every day, 7 a.m. to 8 p.m. I went home to York (Pennsylvania, where they lived at the time) once a week for get a new set of clothes. Irv complained I didn’t have to do that, (that I) could wear the same thing more than once!”
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April 20, 1999 – The power of prayer.
“I prayed each day for any improvement. A toe movement was a cause to celebrate,” Diane recalls three tense months in rehab. “Irv gradually got arm movement – a small victory, as he would be able to feed himself.”
Amid the tears and fears, there was also laughter. “One day, the occupational therapist said he was taking Irv to their kitchen and laundry area. I said, ‘Why? He’s never cooked, and never did the laundry.
“They laughed. They understood.
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“I did suggest we should venture to the airport. The OT obliged though it’s something they’d never done. I knew he’d still want to travel, and that it would take some coordination. Nothing is easy for someone in a wheelchair.”
Case in point: Coming home from Iroquois last May, Irv nearly choked to death on a barbecue sandwich at the Nashville airport. “I was unable to (personally) thank the Navy Seal, a nurse and a doctor who appeared out of nowhere to save his life,” Diane describes the surreal scene. “His guardian angel must have been on duty that day. It was that serious.”
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Diane and Irv at the 2018 Virginia Gold Cup Races. Their Warp Factor, trained by Cyril Murphy, took home the win in a maiden special weight race.
Douglas Lees photo
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The quotable
Irv Naylor:
Asked for his wife’s best attribute, Irv channels his inner imp. “A good … ass.”
Across the patio, his afternoon caregiver can’t stop laughing.
Diane rolls her eyes. “Do men’s brains ever rest? Fortunately, I have a thick skin and a wicked sense of humor.”
Irv settles down and delivers the more considered response, peppered with palpable affection and appreciation. “Seriously. Diane helped me in many of my businesses and now with the farm and the horses and my life,” he says with admiration. “I’ve always respected her opinion and her judgment.
“I admire her creativity and her tenacity. And her ability to rise to the occasion – no matter what.”
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April 24, 1999 – A helicopter to buzz Hunt Cup? No. Just no.
Just days after the fall, Irv tried to convince his doctors he could rent a helicopter to watch Emerald Action run in the April 24 Maryland Hunt Cup.
“I’m sure Duck Martin would have been thrilled to have a ’copter overhead,” Diane chuckles at the thought of them buzzing the Glyndon racecourse.
They didn’t do it, but, “at Irv’s insistence, I attended,” Diane says. “Most of the crowd was rooting for him.” Emerald Action – the horse that had fallen with Irv the week before, finished second to winner Welter Weight after leading over the 19th with trainer Jack Fisher aboard.
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The 2000 Grand National Timber Stakes. Emerald Action (right) with trainer Jack Fisher leads Stopped Silence and trainer/rider Neil Morris over the 9th fence. The race was won, ironically, by Welter Weight and Michael Elmore - the same duo who defeated Emerald Action in the 1999 Maryland Hunt Cup.
Douglas Lees photo
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A deep, dark place.
“It changed my life incredibly,” Irv told the
Baltimore Sun 10 years ago. “Even more so (it changed) Diane’s life. I don’t know what I would have done without her.”
Bitter and depressed, at first Irv fell into a hellish spiral. “I was really angry that it happened to me,” he told Mike Klingaman in a
2018 article. “A friend got me three pistols, but my hand was so crippled that I couldn't use the damn things.
“I asked the doctor, 'How many pills would I need?' 'Forget it,' he said. 'You'd have to take too many and you'd probably die trying to get them down your throat.' ”
Still, Diane says it wasn’t too long when the man she knew re-emerged. “He was back to typical Irv – ‘I’m not giving up, and I’m not going away’.
“That’s who he was before, and that’s who he is today. He’s a special, special man.”
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The quotable Cyril Murphy:
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Farm trainer Cyril Murphy, 48, has been at Stillwater since 2013. The Waterford, Ireland native has trained two of Naylor's three Eclipse ’chase champions – Dawalan in 2015 and Rawnaq in 2016.
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Dawalan (left) and Rawnaq duel to the finish line in the November 2015 Colonial Cup. Dawalan emerged victorious.
Tod Marks
photo
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Murphy says the coronavirus shutdown of racing means his twice-weekly working lunches with Irv and Diane these days are about his daughter’s online schooling and the latest pandemic news. He looks forward to shifting focus back to the horses (Murphy has – had – 12 in training) and race plans soon.
“They have a great, long dining table in the house,” Murphy describes social distancing, Stillwater style. “Irv sits at one end, I sit at the other. Mrs. Naylor is a very good cook, excellent. Tuesday we had this great shrimp salad. And she does a wonderful chicken salad. Everything’s homemade, of course.”
Murphy sees the strength in the Naylors’ relationship. “Diane is his rock. She keeps everything in balance …. tends to act as the ‘conscience’ on his shoulder about some of the bigger (horse) decisions. She’s a strong background support team. She never wavers.”
Underneath the strong exterior, Murphy says, there’s a soft touch, too. “A side of Mrs. Naylor that most people don’t see – she’s all-business, but she’s (extremely) thoughtful. Back when Rawnaq won the Eclipse (2016), she pulled off a real surprise.
“She asked me to dinner one night to help (entertain) some friends, she said, visiting from England. We walked into the living room, and there was my mom. Unbeknownst to me, Mrs. Naylor (and Murphy's wife, Becky) had arranged her to come from Ireland, plus the Naylors had gotten me my own Eclipse Award, with a plaque with my name on it, as trainer. That was really special.”
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Ross Geraghty, Diane Naylor, and Cyril Murphy celebrate after Dawalan's victory in the 2015 Colonial Cup.
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Just the facts: Irv Naylor
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A native of Stevenson, Maryland, Irv’s father operated a filling station in nearby Pikesville. His introduction to the horse world was through his grandfather and uncle, both blacksmiths; Irv captained McDonogh military school’s cavalry squad his senior year.
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Graduated Miami University and launched Lok-Box in 1960, a packaging company that produced wooden boxes. He added Cor-Box – corrugated boxes – in 1968. Sold Lok-Box in 1980, Cor-Box in 1999.
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Three children – Vivian, Scott and Peter (Vivian died a few years ago at age 59), seven grandchildren and three great-grandchildren
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From the Grand National Steeplechase in 1998. "American Steeplechasing" says:
The Grand National celebrated its 100th Anniversary in style, bringing back a host of former competitors to serve as "jockeys" and officials for the Wild Goose Chase, a non-sanctioned flat race.
Naylor (top row, hat raised) won on his Tarsky. Douglas Lees photo
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Irv Naylor, jockey:
Rode 41 races, beginning at the April 22, 1967 Grand National meet, and ending at the April 17, 1999 Grand National meet. His biggest win was at the April 20, 1996 Grand National, the allowance with Emerald Action. Naylor rode, and completed, the Maryland Hunt Cup four times – two fourths, a fifth and a seventh.
“I wish I could have won the Hunt Cup as a rider," he told the Baltimore Sun. “I loved flying over those fences.”
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Owner-rider Irv Naylor found the winner's circle in in a sanctioned race in 1996 for the first time since 1964. Irv and Emerald Action, an Irish import, won the Murray Memorial at the Grand National Steeplechase Races. Naylor's previous riding victory in 1966 came in the Murray's predecessor, the Western Run Plate, aboard Arthur.
Douglas Lees photo
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Naylor, owner:
* NSA leading owner in 2010, 2011, 2012, 2014, 2015 and 2016; has about 40 horses with seven different trainers
* Two Maryland Hunt Cup winners — Make Me A Champ (2005) and Askim (2008.) Five Virginia Gold Cup wins (retired the perpetual cup, and replaced it.) Ebanour won two Gold Cups and Pennsylvania Hunt Cup twice, My Lady’s Manor and the New Jersey Hunt Cup.
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2005 Maryland Hunt Cup presentation for Make Me a Champ: Diane Naylor on the left, Irv Naylor, Joe Davies, Blythe Miller Davies, Bruce Miller (trainer of Make Me A Champ) and Joe's mother Eleanor Tydings Gillet Schapiro.
Douglas Lees photo
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Naylor, on hope: Disability is not the lack of ability, but rather, the lack of solutions.
In 2016, the
Keck Institute reported hopeful rehabilitation news of a 21-year-old quadriplegic. Kris Boesen was paralyzed from the neck down in a car accident; two months later, using the stem cell research supported for decades by Irv Naylor and others, Boesen got back most of the feeling in and use of his arms.
“I truly admire Irv’s spirit – he does not give up,” Diane says. “He’s devoted so much time and money into stem cell research in the hopes for a cure, and he maintains his sense of humor and a will to fight on and live life to the fullest.”
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Naylor, on self-control:
He told Sun reporter Mike Klingaman
in 2018 that he struggled with frustration at first. “I’ve been through a half dozen operations on (my hands), and there is still no real value. Writing is difficult – I have a hard time handling paper. People not in a wheelchair don’t know what it’s like to be totally dependent on other people, especially for a proud person.”
Naylor, on his future:
“Well, I'm not walking, but I'm not dead, either," the now-85-year-old also told Klingaman. “The last thing I want to do [in life] is to dance with my wife. But I haven't done that, so I can't die.”
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Naylor, on what he wants on his gravestone: “He done his damnedest.”
Diane acknowledges the sincerity. “Seriously, underneath it all, he’s a real softie,” she says. “He’s this strong, serious businessman, really successful and really driven. But I’ve seen him do things for people that are so generous and kind.”
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