Every now and then, when the mood struck him, Alfred G. Vanderbilt Jr. would stop shaving.

After a couple of days, he’d pull a hat down over his brow and get dressed without putting on a tie. He’d forego the reserved boxes and the company of Broadway stars and slip in with the masses through the general admission gates of Belmont or Pimlico, where he was a track executive. Amazingly, at a time when Vanderbilt could appear in the society pages simply for going out to dinner, his son Alfred G. Vanderbilt III doesn’t think anyone ever recognized him while he was incognito.  

“He would look as much like anybody else as he could and see how people were treated,” said Vanderbilt III. “Then, he used to raise hell at the board meetings about how people were being treated when they came to the track. So, he really did know what they liked and he knew what they were about. I think he had the personality of a promoter a little bit.”

Vanderbilt was, in many ways, racing’s renaissance man. The highlights of his career in the sport will always be his success as owner/breeder through his Sagamore Farm in Maryland, and his time as owner/president of Pimlico Race Course, president of the Westchester Racing Association and later, the New York Racing Association. But underneath it all, Vanderbilt III remembers his father as a natural marketer with a command of skills that served him well in his role managing racetracks.

Young Vanderbilt grew up reading the Daily Racing Form (which was delivered in a paper wrapper to avoid detection by his teachers at St. Paul’s School in Concord, N.H.) and running a winter future book on the Kentucky Derby for his classmates. Vanderbilt left Yale University to make his life in the Thoroughbred world.

“I just always thought it was more fun and more exciting than anything else,” Vanderbilt told The Thoroughbred Record in 1986. “And I was not in love with horses, really. It was like the kid who was crazy about the circus and didn’t really care about the elephants. It was the whole business of the excitement. My mother had horses and a trainer who took the time to teach me and tell me what he knew. There’s just never been anything else I wanted to do as much as this.”

Alfred G. Vanderbilt II

More than 30 years later, Vanderbilt III looks back on that quote as a perfect example of his father’s feelings.

“That’s something a promoter would say. And I think it’s true,” he said. “I think he liked seeing people go through the turnstile. Every time I went to the track with him, he’d find out what the gate was. He wanted to know everything.”

Despite his position in one of America’s oldest and wealthiest families (he was great-great-grandson to Cornelius Vanderbilt, who made a fortune in railroads), Vanderbilt knew full well there would be no racing without an audience of average Joes. He bought stock in Pimlico while still in his twenties, and in 1938, when track shareholders balked at the notion of serving alcohol at the races, Vanderbilt offered to buy them out and wound up owning the facility. Under his direction, the “Old Hilltop” in the infield that obstructed the public’s view of the race was hauled away. He added a public address system so fans could hear the call, a starting gate so bettors could feel more confident in the race’s integrity, and raised purses.

He also organized one of the biggest public spectacles in the sport: the match race between Seabiscuit and War Admiral.

Vanderbilt III is too young to remember the organization of the famous match race, but he’s heard stories.

The elder Vanderbilt had made pitches before to Seabiscuit’s owner Charles Howard and War Admiral’s owner Samuel Riddle for the two-horse race, as had his rivals at the New York racetracks, all to no avail. In 1938, he pleaded with Riddle one last time and was given a list of three conditions (both horses should carry 120 pounds, and he wanted a walk-up start with his choice of starter) that must be met for War Admiral to appear, then had to sweet-talk Howard into agreeing to them. He even had to physically chase Riddle through Penn Station and block him from boarding a train before getting the final signature on a contract between the two men.

“I forget which one of them agreed first, but they said, ‘Sure if you can get the other guy to do it,’” Vanderbilt III recalled. “So he went to the other guy and said, ‘I’ve got him!’ which of course he hadn’t quite done. The first person who ‘committed’ didn’t really quite commit. Again, there’s your promoter. Dad had a good healthy ego and he wanted that win, that race in his place. He was a very, very well-respected man, even in his thirties.”

The famous match race between Seabiscuit and War Admiral at Pimlico Race Course.

Vanderbilt inherited Sagamore Farm in Maryland at the age of 21 and determined to make it into a household name among the racing set. (He was not presented the farm as a gift, a myth which irked him immensely and appeared in many feature articles over the years, as well as a few obituaries. Isaac Emerson, Vanderbilt II’s maternal grandfather, made his fortune as the inventor of the antacid Bromo-Seltzer and after the Civil War traveled across the country buying up farm properties as investments. Sagamore was one of them, and it was left in trust to young Vanderbilt.)

Rather than pay people to do the thinking for him, Vanderbilt the promoter knew he would be best-equipped to sell the product of the racetrack — and to run his own stable, if he had hands-on experience. He kept the stock he inherited with the farm with trainer J.H. “Bud” Stotler and asked the trainer to show him how things worked. Vanderbilt ended up as an unofficial assistant trainer for Stotler, taking second-string horses around to some of the less glamorous tracks.     

He was an excellent writer despite having no formal training as such. Legend has it he spent part of a racing afternoon with an unidentified sports columnist who had a little too much to drink as he stressed his way toward a deadline. The man passed out on his typewriter, and Vanderbilt took over the keys, finished writing the copy, and turned it in.

“He was friends with Ernest Hemingway, who proposed him as a columnist I think to Esquire,” Vanderbilt III remembered. “They didn’t end up doing it, but it was a pretty good recommendation.”

In later years, Vanderbilt exercised his command of language when naming his horses. He was famous for clever jokes built from a sire and dam’s name (Social Outcast was by Shut Out out of Pansy; Ogle was by Oh Say out of Low Cut; Dirty Old Man by Tom Fool out of Last Leg). He was also a fan of carrying names through families: his graded stakes winner Dundee Marmalade was by Sword Dancer out of Tea and Toast. Tea and Toast was out of Cup of Tea, who was out of Teahouse, a daughter of Polynesian and Geisha.

“This is how I tell people my dad was actually a nerd. He carried in his pocket [a copy of] the breedings, so he could be sitting at the racetrack and he could come up with names,” recalled Vanderbilt III. “He didn’t really like people helping him. He let me try to name one once. It was Secretariat-Cold Comfort and I came up with Social Security which I thought was genius, but he said it was taken. It ended up being Cold Reception, which was fine. Social Security was better.

“The fun, I think, was for the horseplayer. It was like another thing to be looking at when you were looking at the program, to see the dam and sire and get a chuckle out of the way the name was played.”

Vanderbilt’s promoter mentality and sense of humor both came in handy one day when Louis Chery, his long-time butler and valet, came to him asking whether his employer would mind terribly if Chery bought into a racehorse. After sixteen years of accompanying Vanderbilt to the races and early morning workouts, Chery got together with stable foreman J.C. Mergler and Lee McCoy, who was training for Vanderbilt, and bought a yearling in Saratoga. The $3,500 son of Tintagel was dubbed Lands End and kept in Vanderbilt’s shedrow, according to a Baltimore Sun article. Vanderbilt didn’t miss a chance to poke fun at the yellow silks chosen for the horse, describing them as “lemon yellow” or “stop sign yellow.”

But it was Chery and his partners who were laughing when the colt won in his debut under Vanderbilt contract rider Ruperto Donoso, paying $48 on a $2 win bet. Chery and the co-owners had $200 on him.

“When my father’s famous lunch guests started asking Louis for racing wisdom, I remember thinking that Dad’s expression looked … maybe a bit pinched,” Vanderbilt III recalled.

Vanderbilt was eventually recruited to manage New York racing – first via the Westchester Racing Association, and after serving in World War II, as a founder of what is now NYRA. It was there he encouraged the sport to embrace television, serving as on-camera talent himself on a couple of early Belmont Stakes broadcasts.

“I have a photo of him doing a television broadcast, and you can see he’s having the best time of his life,” said Vanderbilt III. “He thoroughly enjoyed celebrity, he really did. He never had a publicist, but he made sure his racetracks had publicity.”

Vanderbilt II had a complicated relationship with celebrity. He enjoyed its perks, but was aware of its drawbacks. His best friends were Broadway stars and later, Hollywood headliners. Theater producer/directors Hal Prince and George Abbott were close friends, and the former was in the habit of asking Vanderbilt’s opinion on whether a song would make a hit – he was usually right. George Gershwin was known to sit down to the piano at parties. Pianist and comedian Oscar Levant lived with the family in New York for two years, and many of Vanderbilt’s friends made it to his box at the racetrack.

“It was a little surreal and it was life. I learned early on that you couldn’t go to school and talk about what happened at home,” Vanderbilt III said. “Because they’d say, ‘What did you do on the weekend? Let’s go around the room.’ And one kid would say, ‘I went to the ball game with my dad’ and another kid would say they had a cookout and so forth. And I could not say, ‘Elizabeth Taylor came up for lunch and then Gen. [George] Marshall helicoptered in.’ I had to say, ‘My parents had friends over.’

“I had a lot of scrutiny, a lot of people assuming how rich I was. I can’t imagine what it would have been like for him. People would have wanted things constantly. I think he was a little bit distrustful because of that. Yet, he also understood the benefits of fame and he liked that quite a lot. He liked it when he turned up someplace and everybody went, ‘Oh my god, it’s Alfred Vanderbilt!’”

Vanderbilt (left) presents the 1941 Withers trophy to jockey John Gilbert and Ogden Phipps

Of course, horses don’t much care how famous someone is, and a person’s celebrity is no guarantee their horses will go down in the history books. But nonetheless, Vanderbilt’s career as an owner was an impressive one, too. While he was still on the track training for Stotler, the trainer advised him to take a look at a young son of Display, whom Vanderbilt bought for $25,000. That horse turned out to be future Hall of Fame inductee Discovery, who went on to race a staggering 63 times with 27 wins, and won the Horse of the Year title for 1935 over Triple Crown winner Omaha. By the time the horse came off the track, Sagamore Farm was ready to stand him.

“Discovery transformed the farm. My recollection was he was always kind of embarrassed that he had to buy Discovery to do that, but it absolutely worked,” said Vanderbilt III. “He inherited his mother’s breeding stock, and he said it was good but it wasn’t going anywhere. Then, they got Discovery and he changed everything practically in a generation. Then you had Find, Loser Weeper, Social Outcast, Bed o’ Roses, there was a whole crop that just came, boom.”

Discovery also gave Vanderbilt one of his most thrilling rides in the sport: Native Dancer (by Polynesian, out of Discovery mare Geisha – another clever name). The gray famously ran 22 times, winning the Belmont, Preakness, Travers, and Met Mile, and lost only once, in the Kentucky Derby (where Vanderbilt had also finished second with Discovery). The horse’s workouts became spectator events, and the racing media followed his every snort as only old-school racing press could. Besides his racing accomplishments, the Grey Ghost of Sagamore was widely recognized as horse racing’s first television star – appropriate, given his ownership.

After Native Dancer’s death, Vanderbilt III wrote for The Blood-Horse in 2003, he went to visit his father, who was not a very sentimental person.

“This once, however, I managed to get him to talk for a minute or two about the dappled gray that changed his life. ‘You know,’ he said, summing it up. ‘that was about the most exciting thing that ever happened to me.’”

Native Dancer appeared on the cover of Time Magazine May 31, 1954

Vanderbilt dispersed some of his stock in the 1950s and sold Sagamore Farm in the 1980s, keeping only a handful of horses in training up until his death. The business had changed from the one he had known. The era of privately-owned stables with trainers and jockeys on retainer, the time of gleaming shed rows shining with the owner’s colors, rather than the trainer’s, racing dominating the society pages along with Hollywood gossip, was gone.

The tax code changed, making it harder for large stables to write off their expenses, and equine insurance grew so high, owners could no longer afford to keep stud prospects in training. Syndicates became the fashion, and Vanderbilt didn’t want to operate that way.

“When I go and give the trophy for the Vanderbilt Stakes there’s usually like 20 people standing there. The trainers are really the owners today. The whole system has swung around,” said Vanderbilt III. “He participated in two or three syndicates and was just really uncomfortable with it. He was an individualist. He had done things his own way his whole life and the idea he would now have to be beholden to two or three other people on decisions he was making, he couldn’t really do that.”

In his later years, Vanderbilt warned the racing business about what he believed were early mistakes. In his 1986 Thoroughbred Record interview, he pulled no punches when he said, “One of the things that I argue with the NYRA people about is the fact that they keep telling us how marvelous it is we’re getting more money from off-track than we are on-track. It seems to me the sensible approach to that is we must be doing something wrong because the people are not staying here and enjoying the product.”

Vanderbilt was elected “The Man Who Did The Most For Racing” by the New York Turf Writers a record four times, and received an Eclipse Award of Merit in 1994.

Vanderbilt died one morning in 1999, after making his daily trip to the racetrack to watch workouts, a tradition he kept up throughout his life.

“People tend to remember him as this nice old man who passed out chocolate chip cookies in his old age,” said Vanderbilt III, noting his father’s favorite form of dispensing cheer on the backstretch. “But that was just one part of the story.”

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