America's growing love of office pools

Football season is kicking off, which means office pools are also in full gear. AP Photo/John Locher

Over the past 16 months, more than $10 billion has been bet in the growing U.S. sports betting market. Legal bookmakers are operating in 13 states, popping up at casinos, racetracks and on your phones. Entire media outlets -- like radio station 102.5 The Gambler in Philadelphia -- are launching to focus on odds, point spreads and parlays.

As football season kicks off, sports betting is in your face more than ever -- and likely in your office, too.

According to survey data released Wednesday by the American Gaming Association (AGA), 11.8 million Americans will bet on the NFL this year as part of a sports pool, squares contest or paid fantasy contest. The survey found 31 percent of people who bet on the NFL do so through pools, slightly up from last year, when the U.S. Supreme Court opened a path for all states to get into the bookmaking business. Overall, the AGA estimates 54 million people -- nearly one in four American adults -- participate in a betting pool annually.

There are survivor and confidence pools and March Madness brackets and pick 'em contests. There are pools on golf and "Game of Thrones." They take place in offices from Goodwill to Google, from fine-dining restaurants in Minneapolis to country clubs in New Orleans.

None of them, though, are quite like the pools that were run for over a decade by two middle-aged New Yorkers whom everyone knew as Ron and Mike.

Ron and Mike's NFL pool

A Woodstock concert poster hung on the wall of a small basement office in an industrial building at 1 Dupont Street, Suite 109, in Plainview, New York. Electric cash counters were on the desks. They were necessary.

Millions of dollars in cash flowed through that office, coming in and out, sometimes in envelopes, sometimes in duffel bags. It was headquarters to the nation's largest NFL survivor pool -- Ron and Mike's.

On Aug. 15, 2006, the URL for Ronandmike.com was created. The following January, Ronald D. Kronengold ESQ., P.C., registered with the New York State Department of State. The address of the company's principal executive office: 1 Dupont Street, Suite 109 in Plainview.

Over the next 11 years, Ron Kronengold and Michael Bernstein ran massive football, basketball and baseball pools. Thousands of people from across the nation -- including betting syndicates -- entered. It grew primarily by word of mouth; new participants needed a "captain" to vouch for them.

Weekly picks were submitted online. Entry fees were typically $100, sometimes $500 for elite pools. Money moved through online payment processors or by mail to a UPS box in Plainview. Prize money often reached seven figures.

Patrons at Manhattan bars would overhear strangers talking about the Ron and Mike pool and say, "Hey, I'm in that, too." A regular participant from New Jersey said that he once overheard two men bantering about "Who are you taking in Ron and Mike?" while at The Venetian Race & Sports Book in Las Vegas. It made him feel like the pool had gotten too big.

At its peak, during the 2017 NFL season, there were more than 20,000 entries in the Ron and Mike survivor pools: 10,000 in each in the "Red" and "Blue" pools. There was plenty of side action and second-chance pools, too.

Heading into Week 13 of the 2017 season, less than 80 entries remained in each of the primary contests. Around $2.5 million was at stake.

"The most amazing statistic," Ron and Mike wrote to participants in a Dec. 1, 2017, email, "is that both the Red and Blue pools have exactly the same number of survivors ... 73. It should be fun from this point forward."

The fun ended abruptly, just days later, at the hands of the FBI. The prize money was seized. No one was paid, and Ron and Mike haven't been heard from publicly since Dec. 6, 2017, when they sent a devastating email to the few dozen players still alive in the pool:

"Please be advised that the Ron and Mike website has been forced to shut down at this time and is unlikely to open again.

"We understand your frustration and anger at this time, but closure of the pool is beyond our control. We apologize to those that are still alive in our various pools and we ask for your patience and understanding while we contemplate the next steps. Unfortunately at this time we cannot make any additional comments."

Details about who Ron and Mike are and what happened to them are scarce. Kronengold has a legal background. Bernstein was active on social media as recently as July. In 2014, the two applied for a patent for a "Sports Game and Method" designed to "combine the features and benefits of fantasy gaming with survivor pool gaming."

ESPN reported that a warrant to seize records and money from the pool was issued by federal prosecutors in the Eastern District of New York. Documentation of the seizure has not been made available publicly, and an attorney currently representing Kronengold and Bernstein declined to comment when reached by ESPN.

Are pools legal?

NBA general managers, Supreme Court justices and deputy chiefs of staff for former U.S. presidents play in pools, often right alongside Jane from accounting and Pete the copy guy's always-savvy grandma Ethel.

Most of them are illegal.

Real-money pools, even just between friends, with no one taking a cut, are "generally illegal in 37 of 50 states," according to a 2018 legal analysis commissioned by the American Gaming Association.

The remaining 13 states have nuanced exemptions for pools. In Washington State, for example, Super Bowl squares pools are authorized, while bracket pools, office pools and fantasy sports are not.

Laws regarding pools, however, are rarely enforced, said Jeff Ifrah, a prominent Washington, D.C., attorney, who has handled many high-profile gambling and sports betting cases. Ifrah recalls only a handful of times in which authorities targeted pools. On the rare instances that authorities do take interest in a pool, Ifrah says that the organizers are usually the primary targets and that disgruntled participants are usually responsible for triggering the investigation.

"It drives you crazy as a defense lawyer," Ifrah said. "It's like, 'Why didn't you just try to resolve that? Why didn't you give him his $10 back?'

"Regardless of the new regulatory scheme that's sweeping across America," Ifrah added, "office pools are probably pretty safe from enforcement, assuming that no one involved is taking a cut just for organizing the pool. Taking a cut essentially brings the organizers under bookmaking in a prosecutor's view. Once you're taking a cut, there's not a lot to distinguish you from a bookmaker."

The dubious legality isn't deterring many from getting involved, though. For many, betting against friends, family, coworkers and even teammates seems more casual and safer than taking on a bookmaker. Even the greatest quarterback-receiver tandem in NFL history love to compete against each other with their picks.

Joe Montana's pool

The Joe Montana family survivor pool is intense.

The annual showdown normally features around 25 participants, mostly immediate family members, along with a few former unnamed NFL celebs. The stakes are kept secret, but humiliation is on the line.

"I can tell you what the last-place penalty is," youngest son Nick Montana said. "They have to sign up for 15 minutes of stand-up comedy and can't mention that they lost a bet."

Survivor pools have become increasingly popular. The general game format calls for players to pick a winning team each week. The player who survives the longest without picking a loser wins the pot. The structure fits the NFL's topsy-turvy balance of power, but, evidently, doesn't suit Joe Montana's prognostication skills. Montana, a four-time Super Bowl champion quarterback for the San Francisco 49ers, is still looking for his first win in the family survivor pool.

Oldest son Nate has the most Montana pool championships, but mother Jennifer is the fiercest competitor. If "J-Mama," as she's often referred to, suffers an early exit, she's been known to buy back in multiple times.

"I don't think she's OK with losing," said Spencer Cassidy, family friend and, along with Nick Montana, an executive in the new family business, Balto, a digital platform aiming to modernize the office pool.

With Joe Montana as an investor, Playbalto.com provides a platform for pool organizers to tailor the rules and run a variety of pool contests. They include a social trash-talking function and eventually hope to provide a safe environment to hold prize money.

"What we've seen in the market is a huge appetite for peer-to-peer betting," Cassidy said. "People feel more comfortable betting with their friends. When you're betting against the book, you're kind of betting into a black vortex."

The popularity of pools transcends to all walks of life and many, like the Montanas, are turning them into a business endeavor. Sports data site TeamRankings.com, for example, says its largest source of revenue is a subscription service for office pool optimization tools.

"Our core customer is going to be someone who is pretty hardcore about this stuff, competes in multiple different pools or one or two pretty high-stakes pools," Tom Federico, co-founder and CEO of TeamRankings.com, said. "But then we have this big contingency of customers who are far more casual. We were just exchanging emails with a lady who's our first buyer every year [for football season] and always tells us how she did compared to her husband and her 82-year-old friend Ethel."

Federico says that more than 10,000 people subscribe to his company's pick optimization tools, including a former deputy chief of staff in the White House, a prominent manager of a $10 billion hedge fund and Daryl Morey, the general manager for the Houston Rockets who allegedly has won the office March Madness pool three straight years.

Pool popularity

Betting pools are an American pastime that can be traced back to horse racing in the 1800s. As baseball rose to prominence in the early 1900s, underground sports gambling parlors known as "pool rooms" opened in big cities like Chicago, New York and Philadelphia. In 1977, a Staten Island bar hosted one of the first bracket pools on the NCAA college basketball tournament, and Super Bowl squares, fantasy football leagues and, more recently, survivor pools became prevalent with the rise of the NFL.

"I'm not sure I've ever worked in a law office that didn't have a pool," an Ohio attorney said.

Betting pools are ubiquitous in the United States, and people absolutely love them -- unless they get busted and suffer the fate of Ron and Mike.

For the few dozen players still alive in the Ron and Mike million-dollar pools, the closure was a crushing blow. Accountants in Miami, marketing execs for non-profits in New Jersey and website designers in North Carolina had endured three months of high-stakes NFL sweats to get into a position to win life-changing money.

Some learned of the pool's fate while researching their picks for Week 14. Others were considering making proposals to chop the pot with the remaining players. For some, it was their last pool.

"It ruined office pools for me. I haven't done one since," said a player who was still alive in the Ron and Mike pool when it was shut down and talked to ESPN on the condition of anonymity. "The rush is gone. Even if I were to do one for $10,000, it's still not the same because of Ron and Mike."

"What the real draw was," another Ron and Mike participant said, "'Man, I can win a million bucks in this pool.' How many times do you get to say, 'Man, if I win this pool, I'll win a million bucks'? I think that was the real ultimate draw, just the pure volume of dollars at stake."

Multiple sources said another high-stakes survivor pool out of New York has emerged and is reaching a high-six-figures prize.

"It's not quite as big as Ron and Mike's," one player said, "but it's getting to be."