Former Microsoft Executive Captures Woodbine 2017 Player of the Year Award

September 27, 2017

​By Eric Wing for

TORONTO, September 27 – Michael Eisen always loved horse racing. But until he retired in 2013 after a long and distinguished career as Microsoft Canada’s Chief Legal Officer, the Toronto native never really had the time or inclination to participate in handicapping tournaments.
“I was not aware of them,” said Eisen, 68. “I was distracted by so many other things, and contests were just not on my radar.”
That all changed in a big way this year.
After dipping a first toe into contest waters last year, Eisen stepped up his play significantly in 2017, participating in each of Woodbine’s four handicapping tournaments during the year. He didn’t finish first in any. But two third-place finishes (in the Woodbine Spring Meet Tournament on June 24 and the Woodbine Weekend Handicapping on August 26-27), a sixth-place performance in the September 16 Woodbine Mile Handicapping Tournament, plus an off-the-board effort in the July 29 Woodbine Mid-Summer Handicapping Tournament combined to put Eisen at the top of the standings in the first-ever Woodbine Player of the Year Series, which is based on a points formula recognizing both strength-of-performance and participation.
For the Series victory, Eisen receives $6,500, plus a paid entry to the 2018 Woodbine Mile Handicapping Tournament (a $3,500 value in 2017) and—very notably for Eisen—a Sovereign Award.
“For me, that Sovereign Award is more than just the icing on the cake,” Eisen said. “It is really special and carries a value that transcends the other prizes. Not to equate myself with the great achievers in the sport, but handicappers certainly do play a critical role in the industry.”
If there was one common theme for Eisen during the four tournaments, it was his penchant for strong finishes—especially in the Woodbine Weekend Tournament when he managed a third-place finish despite finishing the first-day of the two-day competition with zero.
“I’ve found that, in live-money contests, bankroll management is the key to success,” Eisen said. “You have to be willing to bet your entire bankroll knowing that could mean you’ll have a short day. It’s important, I think, to try not to be timid. Sometimes people who start well get cautious, not realizing there are people behind them in the standings willing to bet it all. In these live-money games, you’re not trying to advance incrementally, you’re trying to advance by leaps and bounds.”

When handicapping, Eisen is always on the lookout for horses with sharp early speed. “I like my horses to be ‘on the engine,’” he said. “I find it particularly rewarding when I can find a mid-priced or long-priced horse that looks like the only speed of the race.”
What Eisen also finds rewarding is just the simple experience of a day at the races—especially when joined in the clubhouse or at home in front of the television by his 34-year-old son Ben.
“He loves racing as much as I do,” said Eisen. “We love going and watching the big races together.
And Eisen believes the fun factor is an important aspect of live tournaments as well.
“I don’t go into these things all super serious, competing to the death,” he chuckled. “I thing you should enter because you love the sport. If you get knocked out early, you can still enjoy the time you spend there with the other players.
“It sounds like I’m blowing smoke, but I’ve always considered myself really lucky to have a track as beautiful as Woodbine so close to home. It’s a very clean track and the tournaments are really well run. The staff is very friendly and accommodating and the trackside tent where the contests are held is terrific. The setting at Woodbine is truly excellent.
Eisen admits, though, that within the offices of Microsoft, fellow racing fans were hard to find.
“I was an anomaly,” he said, drily.
Today, there is no such paucity of like-minded hobbyists in Eisen’s post-corporate life. And you could say that tournament play has opened up even more “Windows” in that area. That will be even truer next February when he ventures to Las Vegas to compete in the National Horseplayers Championship for the first time.
You can also count on the soon-to-be Sovereign-Award winner to be a regular presence at Woodbine’s handicapping tournaments next year. He’ll be the guy betting boldly—and having fun doing it.​
TOURNAMENT NOTES—Gregory Ritza finished second in the Woodbine Player of the Year Series, earning $500 and a paid entry into the 2018 Woodbine Mile Handicapping Tournament. Ali T. Aksoy—winner of the Woodbine Mile Handicapping Tournament​—finished third, good for $400 and a paid entry in next August’s Woodbine Weekend Handicapping Tournament.
With Woodbine’s four 2017 tournaments now in the books, the contest circuit’s attention turns to the 2017 Breeders’ Cup Betting Challenge (BCBC)—generally considered to be the most prestigious live-bankroll contest in the world. The BCBC is run concurrent with the two-day Breeders’ Cup on November 3-4 and can be played either from the Breeders’ Cup venue, which this year is the Del Mar Thoroughbred Club, from one of two satellite locations—Churchill Downs and Gulfstream Park—or online via Buy-in is $10,000 (U.S.), of which $7,500 goes to the player’s live bankroll. Or you may try to compete online for BCBC entries through qualifiers held each weekend at
Eric Wing is the Communications Director at HorseTourneys and the longtime emcee at the National Handicapping Championship. Prior to joining HorseTourneys, Wing headed up Communications at the National Thoroughbred Racing Association and The New York Racing Association. Eric’s Player Profile will be published monthly on the last Friday of each month on