Jonathan always understood the gambling aspect of the Sport of Kings. It was a way of life in his family. Winning days were celebrated and losing ones were lamented. As a kid summering in Saratoga, winning meant dinner at the Wishing Well, Trade Winds or Mangino’s while losing meant Mike’s Subs. Either way it was fun and Jon learned to be both a good winner and, of equal importance, a good loser.
The mutual window where Jonathan’s Dad worked for many years. Jon practically grew up hanging around that window as a young boy and teenager.
In August 1979, when he was 17 years old and at Saratoga with his family, Jonathan realized how profitable it could be to have an edge at the racetrack. One morning, at the motel where he was staying with his parents, the racetrack enthusiasts were sitting around having their morning coffee. The talk of the day was The Alabama Stakes and the consensus was Calumet Farm’s Davona Dale would take it under Jorge Velasquez. Jonathan observed how everyone felt that way from horsemen to handicappers, and even the TV analysts whose opinions were flashing across the television. Davona Dale was the headline in the Daily Racing Form as she should be, having been just the 5th winner of NYRA’s Filly Triple Crown at the time. Jonathan was at the Acorn, Mother Goose and Coaching Club American Oaks where Davona Dale had won giving her the filly Triple Crown title so he knew how tough she was but also knew she was not unbeatable.
After studying the Form all morning, Jonathan’s opinion differed from the masses. It wasn’t just any opinion either; He was beaming with confidence. He believed the problem was not in beating Davona Dale with Harbor View Farms It’s In the Air, which the Form told him was faster and would have the lead all the way around, but how to have enough money to bet to make it count. Though in the minority, he believed in his opinion. Jonathan spent the ride to the track explaining to his parents why there would be an upset in the Alabama and how the fastest horse was not going to be favored. He believed the chestnut daughter of Mr. Prospector out of a Raise a Native mare under heady rider Jeffrey Fell was going to win it. He just knew it. He spent the afternoon holding on to the $400 or so he had and borrowed whatever he could from everyone he knew at the track, promising to pay them back later that day or by the end of the meet, one way or another. He figured he could work at the track for the remaining time if he needed to pay any debts. By race time he had close to $1500. He bet it all! He didn’t hold on to one cent. At 17 years of age he had made and won his first $1000 win bet actually wagering closer to the $1500 he had. That was a lot more money in 1979 than it is today. By the time they hit Mangino’s everyone was paid back with a little extra. From that day forward Jonathan has been a very dangerous bettor.
There have been many scores and of course tough beats since that summer day at the Spa. None were tougher than Mambo in Seattle losing that Travers photo, and Swain not winning the Breeders’ Cup Classic over Awesome Again. Jonathan had that Breeders’ Cup pick 6 with Awesome Again but Swain might have been for the whole pool. He was alive to him also.
His best day came August 10, 1994 at Saratoga with a 540k pick 6 hit, one of only two winning tickets. There was also an only ticket pick 6 at Gulfstream Park for 126k anchored by a single in the last leg. Secret Status was her name and a few months later she would win the Kentucky Oaks. There was another Saratoga pick 6 again anchored by a single in the last leg, New York Dixie, ridden out of traffic by Garrett Gomez to get up in the last jumps for a healthy 143k or thereabouts. On Breeders’ Cup Friday 2013, Jon almost swept the entire pick 6 pool of over one million dollars. On a ticket of less than $200 he posted on Twitter, he had five of six only missing a 25-1 single in the filly juvenile turf whom, which if she had won, he would have had it all. That filly was Dancing House who went on to win to be a stakes winner.