Hunter Thompson wrote, “When the going gets weird, the weird go pro.”Lately, in the contest world, the weird thing is how much success the pros have been having. Last weekend, there were three important on-site contests, two at Keeneland and one at the Orleans in Las Vegas. In each one, a professional horseplayer triumphed. On Saturday, Sean Boarman won more than $20,000 in cash and prizes at Keeneland in a $500 buy-in event, while Duke Matties won more than $50,000 in Vegas. On Sunday, Toronto’s Tommy Massis became the biggest winner of the weekend, taking home more than $60,000 in cash as well as seats to upcoming tournaments, including the Breeders’ Cup Betting Challenge, which he’ll seek to win for a record-tying second time.It’s worth noting that contests in general aren’t really a part of the business plan for any of the three weekend winners, but they all have their own reasons for playing. Of the three, Boarman seemed the most interested in talking about contests from a business point of view.“I think they’re a good way to supplement my steadier income from daily bets,” said Boarman, a Lexington, Ky., native. “They are a good way to maximize my returns on days when I actually have opinions.”True to that quote – and against what might be described as the instinct of nearly all contest players – Boarman is happy to pass a contest situation on a day when he doesn’t have horses he really likes. That’s why even after hitting for $20,000 on Saturday he elected to pass on the $3,000 buy-in on Sunday. “Historically, I know that I don’t do that well on off-the-turf days, so I decided the money could be better applied elsewhere,” he explained.Boarman admits to having his competitive fires stoked by the tournament scene. “A lot of these guys are good friends, but they’re also competition,” he said. “Everybody thinks they’re the best horseplayer, and it’s nice to confirm that against the best players out there.”Massis, now a three-time winner at Keeneland (twice in their big contests and once at the BCBC) prefers dirt racing to turf racing, so he was undeterred by the conditions. “At Woodbine, I work really hard and I really know a lot about what’s going on,” he said. “When I get to Lexington, I relax and just open up the Form the night before. There’s something about that place where I’m just unconscious.”The Hammer, as he’s known, rejects the idea that he has any special edge in contests, at Keeneland or anywhere else for that matter. “I’m not looking to play contests,” he said. “I think the rules are horrible and they don’t prove anything about who we are as horseplayers.”Massis would prefer to see formats where the board is opened up to more horizontal wagers. “If there were pick threes and pick fours, I’d play every contest,” he said. “I’d even join the Tour.”His stated reason for playing the contest recalled George Malory’s famous line about why he climbed Everest: “Because it was there.”“It was just part of my trip and I was going to Lexington anyway and the contest happened to be that weekend,” he said straining credulity. “Between what I spent on travel and betting money I figured, what’s another $3,000?”So why does he choose to compete, despite his complicated feelings? “I enjoy some of the people I meet there, and we’re having fun,” he said.Indeed, Massis made Green Room history on Saturday with a root that proved very popular. As his 19-1 winner hit the line, he banged his fists on the carrel where he was sitting, sending surrounding horseplayers into hysterics by announcing, “Ladies and gentlemen, we have a new leader!”As for Southern California’s Matties, whose family has a rich history in contests, as a professional, he doesn’t love the way that live-bank contests typically force a player to bet so much late to have a real chance to win. “When it comes down to the end and I’ve got $20,000, I feel like I should take that home because I worked hard to get it,” he explained. “I bet every day. The math may be there to make the big bet because if you win in the race you get so much more, but on the other hand, in my mind I don’t feel comfortable with that scenario.”He also is a believer in the good times one can have at tournaments, especially in Las Vegas. “They’re so much fun,” he recalled. “My family and friends all go and we’re together for 10-12 hours every day. We play horses, go to dinner every night, and play craps for three days.”Even with the success he’s had, he’s not sure he’s overall in profit at the Orleans tournaments. They’re more about the social experience. But he does pay special attention to the National Horseplayers’ Championship, because of the ability for an outsized score. He won more than $100,000 back in 2016 when his brother Paul was the champ, netting $850,000. “That can be a life changer,” he said. “When you can win close to a million, it’s a different story.” Loaded DRFT calendarThere’s another weekend of action coming up on DRF Tournaments. Saturday’s featured games include chances to win into the World Championship of Handicapping and Santa Anita’s Closing Day Challenge, a live-bank event happening Sunday, Nov. 4. On Sunday, a qualifier for the Horse Player World Series takes center stage – that’s a three-day mythical-money event taking place at Orleans Las Vegas on March 28-30, 2019.Players also should be on the lookout for feeders into the next $960 Pegasus World Cup Betting Championship qualifier, which will take place on Breeders’ Cup Saturday, Nov. 3 (1 in 15 entries will win prizes worth $12,500). The Pegasus seat is a sweet prize, worth $12,000, all of which will act as a live bank for the contest, which will be held Jan. 25-26 at Gulfstream Park.For much more on everything happening at DRF Tournaments, go to tournaments.drf.com.