Sports betting: ‘None of us came in as experts’

Meet the early-adopter executives who learned how to make sports wagering a winning bet for their leagues.

By Bill King

Editor’s note: This story is revised from the print edition, and some data has been updated from the charts in the print edition.

Scott Warfield, vice president of gaming, PGA Tour; Keith Wachtel, chief commercial officer, NHL; Kenny Gersh, executive vice president, business development, MLB; Scott Kaufman-Ross, senior vice president, head of gaming and new business ventures, NBAJesse Ward

Late in May of 2018, at the height of a dispute over how states should regulate sportsbooks, representatives from the NBA, MLB and the PGA Tour traveled to Las Vegas for a meeting with gambling operators, hoping to find common ground, or at least a patch of ground that wasn’t smoldering.

Lobbying together in states considering legalization, the leagues had been asking for months that sportsbooks be required to use official league data, share access to information about individual wagers and pay leagues a 1% royalty taken from all bets placed on their games.

The operators had balked at each proposition. 

Having not made much progress during a pair of conference calls, the American Gaming Association suggested they sit down face-to-face, hoping to broker a compromise. In town for Game 2 of the Stanley Cup Final, the NHL’s deputy commissioner, Bill Daly, and chief commercial officer, Keith Wachtel, accepted a last-minute invitation to join the summit.  

Arriving at a conference room at MGM Resorts’ headquarters at the Bellagio, Daly and Wachtel found a room clearly divided. On one side of a long conference table sat Dan Spillane and Scott Kaufman-Ross of the NBA, David Miller and Andy Levinson of the PGA Tour and Kenny Gersh from MLB. Across from them were MGM general counsel John McManus, William Hill U.S. CEO Joe Asher, Caesars Senior Vice President David Satz and TVG/Betfair U.S. President Kip Levin. Sara Slane, the AGA’s sports betting sherpa and convener of the group, sat with the operators. 

“I’ll never forget it,” said Wachtel, who would end up leading development of that league’s sports betting strategy. “Bill and I weren’t sure which side of the table we should sit on. Obviously, we were there to sit on the same side as the properties. But at the same time, given the Golden Knights’ place in Las Vegas and given MGM’s part ownership of the building, we were Switzerland.”

After pausing, Daly split the difference, sitting at the head of the table, with Wachtel at his side.

As expected, the meeting was contentious. They came away without a resolution. Leagues and operators continued to swing at each other in hearings and lobbying sessions and at industry conferences. But over time, they found common ground doing commercial deals, which led to compromise on an approach to public policy.

The ice thawed. Relationships developed.

By the time of that meeting, sports betting had become the responsibility of at least one person at each of the larger leagues. Even the NFL, the last to move on most fronts, had senior executives quietly developing a strategy, though they wouldn’t begin to act on it for nearly two years. For the early adopters, a project had evolved into an all-consuming role.

The NBA added “gaming” to Kaufman-Ross’ title a year before the Supreme Court cleared states to legalize sports betting in mid-May 2018. Gersh added it to his MLB title soon after the ruling. NASCAR, the least bet-on of all the major U.S. sports, made social media head Scott Warfield its managing director of sports gaming a few months later.

Completing the evolution of sports betting from flirty pursuit to broadly accepted purview, Warfield became the first to jump leagues without changing roles, moving to the PGA Tour as its first vice president of gaming last December.       

“None of us came in as experts,” said Miller, a PGA Tour attorney who worked primarily on media deals when he was tapped to assess daily fantasy and then sports betting. “We’re all lawyers and business people and analysts who raised a hand and were just thrown into this gaming world and have kind of learned it on the fly. That does bring you together.

“I’m grateful for that experience and relationships I’ve been able to form through it.”

Raise your hand

Kaufman-Ross was 28 years old and in his third year at the NBA when the head of the NBA’s global strategy team, Andy Lustgarten, asked for a volunteer to look into two percolating daily fantasy operators who were knocking around the leagues, looking for deals.

“I raised my hand in the air,” said Kaufman-Ross, who joined the league after three years at Goldman Sachs. “I’m a lifelong fantasy player. In middle school and high school, when people had lives, I played fantasy sports. That was something I was really interested in. I said I’d love to be the one to dig into this one.”

Lustgarten paired Kaufman-Ross with Spillane, a league attorney who since 2012 had been looking into the potential for sports betting at the behest of then-Deputy Commissioner Adam Silver (see related story).

The first time he met Spillane, the lawyer left Kaufman-Ross with a stack of reports to read to get up to speed on the subject. Their work culminated in an exclusive sponsorship deal with FanDuel that included equity in the company, announced on Nov. 12, 2014. A day later, Silver’s now-watershed op-ed suggesting that sports betting be legalized and regulated appeared in The New York Times.

Kaufman-Ross’ attention instantly shifted to an assessment of the business implications of legalized sports betting. Assigned to calculate what the league should do if that happened, he immersed himself in the operation of sportsbooks, and the way sports properties intersected with them in countries where betting was legal. Building on Spillane’s early learnings, he focused on the commercial implications.

Perhaps because of its ancestral connection to casino hotels, the gambling industry is lousy with conferences. Kaufman-Ross’ first was in San Francisco in 2015, at an internet gambling summit that had Spillane on a panel. The following year he joined Spillane at ICE, a massive London event that attracts attendees from around the world and that has since become an annual fixture on his calendar.

Over the next two years, as a New Jersey case that eventually would overturn federal restrictions on sports betting made its way toward the Supreme Court, Kaufman-Ross contemplated the implications of that happening. 

He met with sportsbook operators and others in their ecosystem on visits to London and Las Vegas, learning how they worked and envisioning what role leagues and teams could play. He wrote a 23-page business plan that would connect the dots on where the NBA could best fit, with strategies that cut across business segments. 

While all of the leagues were forced to contemplate the implications of U.S. legalization, only the NBA felt emboldened enough to engage loudly and proudly.

Even before the Supreme Court ruling, Kaufman-Ross got to know Asher at William Hill and Adam Greenblatt, head of strategy at the U.K.-based sportsbook Ladbrokes, who would later become CEO of BetMGM.

“It was sensible that we were evaluating this because we had changed our position. It made it a lot easier for us to take meetings, to attend conferences, because we were out in the open that we thought this should be legal and regulated.

“We were able to take meetings and be at conferences and people weren’t wondering why. We started building relationships in the space.”

Other leagues watched with interest.

From fantasy to reality

While Spillane and Kaufman-Ross were out building bridges, MLB started its exploration with a quietly formed internal task force comprising chief lawyer Dan Halem; Morgan Sword, vice president of strategy; deputy general counsel Bryan Seeley; and Gersh, the executive vice president of business at MLB Advanced Media, who together traveled to London early in 2017 to peek behind the curtain of the sportsbook business. Shepherded by executives from London-based Genius, which handled betting integrity monitoring for MLB, they visited sportsbooks and met with Football Data Co., owner of the valuable data rights of the Premier League.

League contacts

Executives at U.S. leagues responsible for sports betting business

ATP

Daniele Sano, chief business officer

MLB

Kenny Gersh, EVP, business development
Bryan Seeley, SVP and deputy general counsel
Casey Brett, VP, gaming and new business ventures

MLS

Chris Schlosser, SVP, media

NASCAR

Joseph Solosky, managing director of sports betting
Tim Clark, SVP and chief digital officer

NBA

Scott Kaufman-Ross, SVP, head of gaming and new business ventures
Dan Spillane, SVP, league governance and policy
Eric Rimsky, senior director, fantasy and betting partnerships

NFL

Chris Halpin, EVP and chief strategy and growth officer
Nana-Yaw Asamoah, VP, business development

NHL

Keith Wachtel, chief business officer
Conal Berberich, VP, legal
Jason Jazayeri, senior director, business development

PGA Tour

Scott Warfield, VP of gaming
David Miller, VP and assistant general counsel
Norb Gambuzza, SVP of media and gaming

WTA

Dan Fromm, senior manager, partnerships

At the time, few at MLB would have been aware of Gersh’s history astride the gambling industry. Early in his career, he was general counsel at Sportsline, which was on its way to becoming the dominant operator in pay-to-play, cash-prize fantasy. That sort of fantasy had a close enough connection to sports betting that Sportsline bought two companies that produced gambling content, oddsmaking service Las Vegas Sports Consultants and odds tracking site Vegas Insider.

Because LVSC distributed odds, its executives had to be licensed by Nevada gaming regulators, which meant Gersh had to get up to speed on gambling regulations and procedures.

Though Sportsline soon had to divest its gambling-related holdings in order to obtain rights to stream March Madness for CBS and the gambling-averse NCAA, Gersh came away with his first experience with the gambling industry.

A few years later, he made his first contact with baseball, striking several fantasy deals with MLBAM. A relationship with BAM CEO Bob Bowman led to a job there as senior vice president of business development. Gersh quickly went to work building a fantasy portfolio for MLB. When daily fantasy sports arose, Gersh was bullish on it. In 2013, he closed a deal with DraftKings that included equity in a company then valued at $15 million.

As it did for Kaufman-Ross, DFS became a natural bridge to sports betting for Gersh. He was an obvious choice for MLB’s gambling task force led by Halem.

The group came away from that London visit convinced that baseball had vast betting potential if operators could be convinced to innovate in pursuit of growth. They planned to recommend a strategy they could test in Mexico, where sports betting was legal, baseball was culturally relevant and time zones were their friend.

“Then,” Gersh said, “things started happening very quickly.”

Soon after the group presented to Commissioner Rob Manfred in June of 2017, the Supreme Court agreed to hear the sports betting case. MLB then sold BAM Tech to Disney. Manfred consolidated baseball’s remaining internet division into MLB. When the court ruled the following May, he offered Gersh a newly created role as executive vice president of gaming and new business ventures.

“It was great timing for me because BAM Tech had just gotten sold, there was consolidation at the league level and sports betting was taking off,” Gersh said. “In my opinion, this was going to be a great area to be in; the next big thing in sports, which I think it has turned out to be.

“My focus those next two years was almost entirely on sports betting.”

Finding a place

MLB and the NBA each played a role in the PGA Tour’s cautious pivot into betting circles.

Like most sports leagues, the tour’s first deal in the sector was with an integrity services provider, Genius, which it struck in 2017. That deal came about after MLB’s Seeley invited tour lawyer Miller and Andy Levinson, vice president of tournament administration, to the All-Star Game in Miami, where he introduced them to executives from Genius.

A few months later, they attended Sports Betting USA, a two-day conference in New York that brought interested stateside partners together with the established European sportsbook business. The Supreme Court hearing of what then was known as Christie v. NCAA was a couple of weeks away.

Spillane was the only speaker from a U.S. league or team.

“Andy and I were in the crowd and we weren’t sure we were supposed to be there,” said Miller, who, like many, found himself looking into sports betting because he’d previously worked on daily fantasy. “We were sort of worrying whether we were doing something wrong. There was a rumor that MLB was there but I don’t think we ever saw anyone. It was almost like we were worried about people seeing PGA Tour on our name tags at a betting conference. It’s funny to think about now.”

During the conference, Miller and Levinson had lunch in midtown Manhattan with Spillane and Kaufman-Ross. They discussed ways leagues could collaborate on matters. If sports betting restrictions fell, as some predicted, that would lead to either a federal construct or state-by-state legislation. Both preferred the former. But, either way, the leagues would want a say.

A few months later, the tour joined the NBA and MLB in a lobbying coalition that continues today, working in states as they consider legislation and regulatory frameworks.

It was a radical reversal for U.S. golf at that time.

When tour leaders asked Miller to evaluate the emerging DFS business in 2015, they eventually decided the connection was too risky and stayed away. Approached around that same time about licensing the tour’s data for use by betting operators in legal markets overseas, the league again said no.

But as sports betting talk percolated in 2017, the tour had a new commissioner, Jay Monahan, who had encouraged his organization to at least explore DFS and data deals, even if it didn’t end up making them.

“We didn’t have many lawyers, so just by default I got involved,” Miller said. “Every league had to sort of repurpose people to figure this out. At that time, the leagues were looking around and people got involved by default or by raising their hand. I got involved through a combination of those.”

Executives to educators

At NASCAR, Warfield raised his hand. “Itchy” in his role heading social media strategy as the 2017 season closed, he approached his boss, Senior Vice President Brian Herbst, about doing something different. He knew Herbst was exploring the impending sea change anticipated from sports betting. He suspected there was no way he’d have time to handle it himself much longer.

“I want to help you with sports betting,” Warfield told Herbst, “because you’re going to need it.”

By the time the court ruled in May of 2018, Herbst agreed. It began as a side job, but by the end of the year Warfield was spending three quarters of his time on sports betting. In December, NASCAR made it official, baptizing him as its first managing director of gaming. He went to London, where Genius trotted him through the sportsbooks and introduced him around at the first day of Royal Ascot, a horse racing event dating back more than 300 years that annually attracts the queen.

Warfield made a dozen trips to Las Vegas in 2019 alone, meeting with any sportsbook executive that would have him. He had lunch in New York with MGM’s president of interactive gaming, Scott Butera. He ate a turkey leg at the Iowa State Fair with William Hill’s Asher, an ardent Joe Biden supporter who coupled the opening of an Iowa retail location with the chance to put a jelly bean in Biden’s jar at the fair’s presidential primary poll.

He blanketed the conference circuit, quickly graduating from the audience to the stage.

“At one point in 2019, every other week you’re in the Meadowlands or in Vegas,” Warfield said, “and you’re on a panel with Scott and Kenny again.”

The interplay between the league’s betting business designees was different from what they’d encountered in their jobs previously. Though Warfield and the NHL’s Wachtel typically were outside of the lobbying collaborative, they all shared interests on the commercial front.

“Any time that you have a nonexclusive category, which is rare in sports, you tend not to compete as much,” Wachtel said. “I knew Kenny well from our relationship with MLB Advanced Media. I’ve gotten to know others well since. So the ability for us to have those conversations early on and share best practices without really a concern for a competitive advantage was there — and it is not always there in this business. There were a lot of unknowns in betting. So let’s get educated on it together.”

As they got that education, they became the educators, helping craft league strategy that intersected with almost every facet of the organization.

“I was in a fortunate position where I was the unquestioned expert at the league on the topic,” Kaufman-Ross said. “In 2018, I was 32 — so relatively junior — and being put in front of owners and team presidents on a regular basis to explain what the league strategy was, what teams should be doing and how we were thinking about it. I grew up very quickly, because this thing that was happening was the biggest thing in sports, and I all of a sudden became highly in demand to participate in a lot of these things. That certainly was a whirlwind for me, going very quickly to making presentations to owners and team presidents.

“That’s sort of what the trajectory looked like. I was just sort of thrown into the deep end, but very much with the support of the league saying: We don’t care what your title is, we don’t care how old you are, you’re our guy on this and we trust you to drive it forward.”

‘There is no template’

Though some of the topics have changed, the calls have not abated.

Gersh and Kaufman-Ross have expanded titles with new responsibilities outside betting. Miller and Spillane have returned to other legal matters. Wachtel is pretty sure others in the sports business are back to looking at him as the NHL’s “commercial guy,” rather than its “betting guy,” though he concedes that most in the gambling business see him as the latter. The leagues all have staffed up in the area.

Still, sports betting remains white hot, and by comparison brand spanking new, and all say they’re glad to be in the middle of it.

“You can go most of your career without an opportunity to get in on the ground floor with something this unique,” Warfield said. “It’s scary. It’s unnerving. There is no template. There is no playbook. And that either energizes you and you wake up excited about it or it terrifies you. And there are days it terrifies me. But nine out of 10 days it’s exactly the type of thing that I think I was chasing when I jumped from this discipline to that one earlier in my career, because it’s as close to what I would assume it’s like to be starting your own thing.” 

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