HPWS winner Montgomery was born a racing fan

Robert Montgomery never “became” a racing fan. He was simply born one.

“My father’s family has owned, trained, and driven Standardbred race horses for generations,” explained the 54-year-old from Ottawa, Ontario. “When I was 4 years old, I was jogging horses on my grandfather’s knees.”

He switched to betting Thoroughbreds many years later, when his sons were younger and he couldn’t get out to the farm or track. That transition has worked out well for Montgomery: Last weekend he bested a field of 428 entries and won more than $230,000 at the Horse Player World Series at the Orleans in Las Vegas.

This wasn’t his first success in contests. Montgomery finished second in the HPWS in 2012, and in 2016 he won Woodbine’s August tournament. Appropriately enough, his journey in the contest world began at the HPWS back in 2006.

“I saw an ad for it and thought it would be fun,” he said, “and I’ve kept at it because of all the great people I’ve met.”

At this point a big part of his play is related to contests, and not only for financial reasons. “Cash betting is more of a business,” he explained. “Contests are about camaraderie.”

It wasn’t easy for Montgomery at the Orleans, who was under the weather for the entire three days of the tournament.

“My tablemate and close handicapping friend Steve McNatton suggested that I should go back to the room and sleep because I looked so bad,” he admitted. “Patti, my friend and server for 12 years, kept bringing me orange juice after orange juice to nurse me back to health.”

He would basically go from the contest area straight to bed, getting in two hours or so of handicapping in the morning, considerably less than he would have liked for a contest that covered the full cards at several tracks. Still, Montgomery made it work. He embodies many of the qualities that make a good contest player: he’s smart, disciplined, and he knows how to handicap himself. As such, he’s the horseplayer equivalent of a horse-for-course, and his preferred “course” is a multi-track event such as the HPWS.

“I have a very good feel for what races I should be playing: maiden races, turf races, and stake races,” he said. “All my hits were in races that I know I should be looking at. I didn’t waste valuable time, or bets, on races that it just doesn’t matter how much time I spend on, I simply do not have a good track record at picking winners.”

In addition to McNatton’s support, Montgomery also thanked his tablemates Bob Meseke and Phil Hoedebeck. “It makes it so much easier at a fun table,” he said. “Thanks to Debbie and all of her staff at the Orleans for continuing to make the HPWS my favorite off-track tournament.”