03/21/2016 9:45AM

Fornatale: Chicago man wins inaugural Ultimate Betting Challenge


Brian Gross, of Chicago, won the inaugural Ultimate Betting Challenge with a bankroll of $15,013. He also takes home $40,000 in cash and a seat to the Breeders’ Cup Betting Challenge, which is worth $10,000, for a total haul of more than $65,000.

Gulfstream Park and Santa Anita Park jointly held the live-bankroll handicapping contest, but the top three finishers all played at Gulfstream. Will Nefzger, who finished second, and Kevin Jones, who finished third, both earned BCBC seats along with Gross.

Gross and Nefzger led at the end of Day 1 and stayed right there throughout Day 2 despite 126 other players gunning for them. Gross ended Day 1 on Saturday with $16,474.60 and Nefzger with $12,324.

Gross’s big move came early on Day 1, when he jumped up to more than $17,000 after the seventh race at Gulfstream, where My Wish List paid $46 to win and keyed a $1,306.40 exacta with 40-1 shot My Aunt Lilly. “I had two horses I liked, and I couldn’t split them, so I played both and played them to each other, and that made all the difference,” he said.

At the end of the day, he wasn’t sure if his total would hold up. “There were so many experienced tournament players in this contest, and I knew they’d find situations where they wouldn’t be afraid to open up the bank,” said Gross, a traditional pen-and-paper Daily Racing Form handicapper.

Gross, normally a pick four player, chose to keep his strategy the same on Day 2 as on Day 1. He bet more than his minimums in a few races but also was conscious of not betting himself out of position. “I isolated horses I liked and played wins, exactas, and trifectas,” he said. “At the end of the day, whether it’s the pick four or a contest, the game is all about finding above-average payouts compared to the chance you’re taking.”

Gross, 52, is a mergers-and-acquisitions adviser to owners of private companies. His day job shares similarities to the handicapping and betting processes, he said. “In my business, you have nerves of steel, and you can’t be afraid to make a move,” he said.

Gross wasn’t even supposed to play in the contest. His initial plan for the weekend called for a trip to Las Vegas for March Madness. “I was at Gulfstream for the Donn Handicap when my phone ran out of juice,” he said. “I met [contest director] Nancy Berry, and she let me charge my phone in her office and even lent me a portable charger.”

He was so impressed with the customer service that when he learned about the UBC, he canceled his trip in favor of a return to Gulfstream Park.

The night before the tournament, Gross received a positive message from a fortune cookie at Christine Lee’s, where he was dining with his wife, Karen. It read: “The will to do, the soul to dare, is yours for the taking if you prepare.”

“Tournaments are a lot like life,” Gross said. “You can make a lot of mistakes along the way but still finish well in the end.”

Nefzger was down to a mere $312 at one point on Day 1. “At that point, I felt like I needed to get back to basics, trying to grind my way back into it and pick winners,” he said.

That’s exactly what the 42-year-old trial lawyer from Louisville, Ky., did. After hitting the last race Saturday with 15-1 shot Cardiac, he jumped into second place, where he stayed for Day 2.

"I was able to pop it in the last race [Saturday], and here I am," Nefzger said.

The players finishing third through eighth each won a seat to the National Handicapping Championship.

A total of 128 entries played in the UBC, which had a buy-in of $4,500. Fifty-one of the entries came from players who qualified via DRFQualify.com.

Here is a look at the top 11 finishers:

1. Brian Gross (GP) $15,013
2. Will Nefzger (GP) $10,227.50
3. Kevin Jones (GP) $9,648
4. David Nance (SA) $9,475.20
5. Louis Filoso (GP) $8,842.50
6. Hesham Ragab (SA) $7,875.15
7. Tom Arndt (SA) $7,580
8. Frank Mustari (GP) $7,499
9. Mark McGuire (SA) $7,385
10. David McCarty (SA) $7,033
11. Ross Gallo (GP) $6,677.50

In addition to the BCBC seats and NHC seats, cash prizes were $40,000 to first, $20,000 to second, $15,000 to third, $11,000 to fourth, $9,000 to fifth, $8,000 to sixth, $6,400 to seventh, $5,200 to eighth, $4,500 to ninth, and $4,000 to 10th.