Bulls market: Bookmaking tales from Chicago in the 1990s

By David Purdum

The greeting on the Chicago bookie’s answering machine often began with insults and ultimatums.

“42, up yours,” he would bark, calling out account numbers of clients in poor standing. “63, I better see you at the bar to settle up or I’ll come find you. Now, here’s the lines.”

Bettors jotted down the point spreads on the day’s games then left a message after the beep: “This is 63, give me the Bulls for a hundred. Yeah, yeah, I’ll see you at the bar.”

This was neighborhood bookmaking in Chicago in the 1990s. It was raw and rudimentary, but it was everywhere in a time when Michael Jordan and the Bulls were the biggest show in sports.

Twenty-two years ago—on June 14, 1998—Chicago bars erupted as Jordan crossed over Utah’s Byron Russell and hit a game-winning jumper in Game 6 of the NBA Finals. Not only had the Bulls just won their sixth title in eight years, but they also covered the spread as 2-point underdogs. Which outcome resonated more in a city that loves to bet depends on whom you ask. As one veteran Chicago bettor who goes by Geno put it, “When the Bulls were playing, well, it’s not whether they were going to win but just by how many.”

Illinois didn’t legalize sportsbooks until 2019, long after Jordan had hung up his high tops, but sports betting has always been part of the soul of Chicago, with bookmaking a commonplace, albeit underground, profession that dates back over a century in the Windy City.

Bartenders in nightlife hot spots like Lincoln Park normally had connections to a bookmaker, as did the staffs at local country clubs. The heaviest sports betting in town, though, took place at 141 W. Jackson Blvd., on the floors of the Chicago Board of Trade (CBOT).

“It was the first time I was exposed to a true sports betting culture,” said Jeff Ma, who, after spearheading the famed MIT blackjack card-counting team, came to Chicago in the mid-1990s to work as an options trader. “The culture of betting was just pervasive.”

‘Breeding ground for bookmakers’

The grey Art Deco skyscraper on the corner of LaSalle Street and Jackson Boulevard is home to the CBOT. It’s the Wall Street of the Windy City, to a degree. A statue of the Roman goddess of agriculture sits on the roof, and eight bovine heads representing the livestock once bought and sold inside adorn the façade above the original trading floor. It has been a breeding ground for Chicago bookmakers for decades.

The gambling culture at the CBOT spawned colorful characters and wild tales. The bookie who ran his operation on his answering machine worked at the CBOT in the 1990s, alongside many other clerks and traders who battled in the pits during the day and moonlighted as bookmakers on nights and weekends.

“In the pits, there was some pretty big money flying around,” said a former trader and freelance bookmaker who preferred to speak anonymously. “Hundreds of thousands of dollars would be wagered on the Bears’ over/under [on wins in a season]. That was back in the day, though, when the floors were jam-packed.”

One bookmaker was working at the mercantile exchange in the early 1990s, when he scored an early model cell phone that was so clunky, it required a bag to lug it around anywhere. At the time, however, it was cutting-edge technology, and a significant advantage over bookmakers reliant on landlines. The mercantile bookie grew, and the wrong people began to take notice. To avoid detection from authorities and organized crime, the bookmaker and his partner decided to use the bag phone to move their operation offshore.

On weekend mornings, they would drive their boat down the Chicago River, past the bars and clubs that often playfully shoot water cannons at approaching vessels, and out onto Lake Michigan to take the bets over the bag phone. It was the perfect setup, they thought.

On one busy Saturday morning, after logging hundreds of college football bets on pieces of rice paper from the boat, they headed to one of the bars on the river. A buddy at the bar spotted them pulling up and blasted them with the water cannon, drenching the boat and the rice paper with the bets. Writing on rice paper disappears when it gets wet. The record of the day’s bets was gone.

After discussion, legend has it that the bookies chose to pretend as if nothing had happened. When bettors called to confirm their balance the next day, the bookies didn’t question the figures, even though they had no clue how they actually made out on Saturday’s games. No one ever knew.

“Infamously, the bank in the Board of Trade building had more cash in hand than any other bank in Chicago, because people are going in there and getting gobs of cash to pay their guy [bookmaker],” Brian Timpone, a Chicago native, said.

Established in 1848, the CBOT was the first grain futures exchange in the U.S. At its peak in the 1980s and 90s, it claimed to be the largest futures exchange in the world. Everything from pig bellies to point spreads were traded on the CBOT floors.

“On the floor, you basically had a secondary exchange for buying and selling college basketball teams,” Ma, the blackjack whiz and former trader, said. “To the point, you’d literally walk around with a trading card and talk about all the trades that you made that were college basketball teams. You were just walking around trading them with people.

“There was another time,” Ma added, “when there was a challenge to eat 20 cheeseburgers at McDonald’s. There were thousands of dollars changing hands on whether this guy was able to eat 20 cheeseburgers.”

From Capone to Lefty: Chicago’s bookmaking lineage

In the 1900s, bookmakers Mont Tennes and “Big” Jim O’Leary ran sports betting in Chicago. Tennes, a North-Sider, introduced parlay betting on baseball in 1908, and, according to news reports, took a bath, when popular favorites like the Chicago Cubs, New York Giants and Detroit Tigers piled up win after win. O’Leary came from the South Side and ran his operation near the Stockyards in the shadows of Comiskey Park, before suffering a loss from which he could not recover.

“O’Leary was not in on the fix of the [1919] World Series,” Kevin Braig, an Ohio judge and sports betting historian, said. “He took a beating and had to exit the business.”

Mobster Al Capone arrived in the Roaring Twenties and played both sides of the business, taking a cut from many of the city’s bookmakers, while also betting heavily on the ponies, rather unsuccessfully, some say.

“Capone was believed to be more of a buyer than a seller of wagers and reportedly lost hundreds of thousands of dollars backing the ponies,” Braig noted.

The Chicago Outfit, as the city’s organized crime network was known, maintained a piece of the vibrant underground sports betting market for decades. In the 1970s, they expanded to Las Vegas through bookmaker Frank “Lefty” Rosenthal, a native of the Westside of Chicago who was portrayed by Robert De Niro in the movie “Casino.” Rosenthal would run the sportsbook at the ionic Stardust resort in Las Vegas and later emerged as a local celebrity, hosting his own variety show with guests like Frank Sinatra and O.J. Simpson. In 1987, after a flamboyant career, Rosenthal was put in the Nevada Black Book, essentially banning him from the gaming industry.

Meanwhile, bookmaking in Chicago continued. Michael “Jaws” Giorango, a longtime notorious figure in the city, was convicted on federal bookmaking charges twice in 1989 and 1991. In 2004, Giorango took another rap for his role in a nationwide prostitution ring known as The Circuit.

And just this February, 10 men — including Casey Urlacher, a small-town mayor in Illinois and brother of Chicago Bears’ great Brian Urlacher — were indicted on gambling charges related to an offshore sports betting operation allegedly run by a local businessman who goes by “Uncle Mick.”

Indeed, Chicago has a rich bookmaking history, and the 1990s were no exception. Sports betting just looked a little different back then than it does now.

Windy City wagering

Word of mouth was the easiest way to find a bookmaker in the 1990s in Chicago. Getting your buddy to vouch for you with his bookie was the most common way to gain access to the underground sports betting market.

There was an abundance of small-time bookmakers. Some were up-and-comers from the neighborhood. Others were young hotshots who took bets in college and thought they could handle booking in the big city. The problem for the low-level bookmakers was scale. If they grew big enough, they might receive a call from the local Outfit wise guys, offering a business proposition they were expected to accept.

Life was a little less un-nerving for most Chicago bettors, who received an account number, a phone number to call in their bets and a “settle-up amount.” If your account balance was up or down $500, for example, you needed to meet the man. Losers had to pay on Mondays; winners collected on Wednesdays. Settling-up took place in person and mostly in cash.

Pre-internet, the point spreads in the newspapers, either the Chicago Tribune or the Chicago Sun-Times, were the standard in the city. It didn’t matter that the odds were set the previous night in order to make the printing deadline – the newspaper line was what bettors went by and what bookmakers normally offered.

“I do remember some books would have the newspaper line plus a point and a half, meaning if the Bulls were 11, you had to lay 12.5,” recalled a Chicago native and longtime sports bettor who asked to speak anonymously.

In 1995, the bookie preferred by the kitchen and wait staff at Lansing (Illinois) Country Club also put the day’s lines on a recorded message. A female voice — the same one every time – would give the rundown, with the game number, the favorite and how many points they were laying: “604, Bulls 14. 606, Knicks 5.” When finished, she’d say, “Press 2 to place your bets.”

“This guy was pretty big. He had like a crew, the girl and a couple clerks,” Eric Waz, a busboy at Lansing Country Club and novice bettor at the time, said. “I don’t know how big the operation was, but it definitely wasn’t just a one-man show.”

Waz is now a sports bettor in Las Vegas and founder and CEO of sports handicapping website BettorIQ. He began his gambling education coming up in the Chicago area, though, betting around $50 or $60 a game with multiple bookies.

“For a lot of those Bulls’ years, I was still a teenager and was still learning the craft [of betting],” Waz said. “I was still betting parlays, making all the mistakes, taking all the favorites and overs and betting the Bulls a lot.”

Betting the Bulls wasn’t necessarily a square strategy: from the 1990-91 season through 97-98, Chicago went 591-201 straight-up and covered the spread in 54.2% of games.

Jordan’s gambling affinity

Illinois’ new legal sports betting market, once fully mature, could generate more than $10 billion in bets, according to industry consulting firm Eilers & Krejcik Gaming. That’s double the amount wagered with Nevada sportsbooks in 2019.

The Chicago underground betting market in the 1990s certainly wasn’t anywhere near that size, but it was ubiquitous around town – right when an awareness of Jordan’s affinity for gambling was reaching the mainstream.

The tales of MJ’s gambling exploits are legendary. On a road trip in Portland, he reportedly bet teammates $100 that his luggage would come out first at the airport. As the story goes, he bribed a baggage handler to make sure his bags were first. There were allegations of massive losses on the golf course, too, allegations that Jordan has maintained were overblown. When he left the NBA to pursue a baseball career, conspiracy theorists suggested that his gambling was a factor, something both he and former commissioner, the late David Stern, emphatically denied.

Yet, even in a city that loves to gamble, Jordan, at least publicly, avoided getting entangled with the local bookmakers, and, instead, soared to superstardom, transforming Chicago from a Bears’ town to a Bulls’ town in the 1990s.

“I never bet on games,” Jordan said on ESPN’s “The Last Dance.” “I only bet on myself, and that was golf.”

While Jordan says he wasn’t betting on games, plenty were with bookmakers of all levels of sophistication and means.

Perhaps one last tale from the Chicago Board of Trade best demonstrates city’s passion for sports betting. It takes us back to Championship Sunday of the 1998 NFL playoffs. A part-time bookie and determined bettor, who worked the trading floors, was preparing to have a party for the games at his apartment. But, before the party started, he ran until trouble at a Caribou Coffee in the hours before kickoff and ended up at the police station in Wrigleyville. When he called his friends from jail, he didn’t ask them to come get him out, but instead told them to grab a pen and take down his bets before the games kicked off.

What happened when I tried to interview Incarcerated Bob


By David Purdum / @DavidPurdum

I just wanted to interview Incarcerated Bob.

Instead, I got the names of family members and my home address published on Twitter in a threatening manner. I got publicly accused of being affiliated with the “KKK in the south.” Incarcerated Bob even went as far as to fabricate an email exchange between us that never occurred, posting it on his site in a sensational piece of fiction that had me using racial slurs and attempting extortion.

All I really wanted was an interview.

I’ve covered the sports betting industry for five years, for multiple sites. There is an ugly underbelly. What I uncovered this past week is unquestionably the slimiest of all.

Incarcerated Bob first gained notoriety as a regular caller on the Boomer and Carton Show on WFAN in New York. He provided picks and claimed to have inside sources feeding him information about the sports world.

Some people think it’s all one guy running the scheme. Others believe there are just too many Twitter accounts, too many email addresses and way too many ugly stories to be just one person. As with any elaborate scam, though, it is very difficult to nail down the parameters.BobTwitterAccounts copy

But one thing is very clear – Incarcerated Bob was not happy when he became aware that criminal background checks were being performed on a middle-aged man from Elmont, N.Y., named Louis Mendez.

On May 9, 2011, Louis Mendez of Elmont, N.Y., was accepted as a “Tiered Revenue Share Sportsbook Promoter” of an offshore sports book. According to registration records provided by a first-hand source, Mendez signed up under the username Randizzle14, with the email address Randizzle14@gmail.com and phone number with a New York 347 area code. Mendez registered with the website Gamblersfinalword.blogspot.com. At the top of that site, it currently reads “Incarcerated Bob’s Picks-N-Rumors.”

Randizzle, aka @TeamMoneyPicks, is a major player in Bob’s network. Randizzle may very well be Bob, who may very well be Mendez.

According to his Linkedin page, Incarcerated Bob hails from Elmont, N.Y. Mendez’s criminal record lists the same Elmont, N.Y. address, but has him currently residing in Elmhurst, N.Y.

The criminal background checks began last week. It became personal on Thursday.

Before the background checks were completed, I received a barrage of venomous tweets from @BigEastProfit, one of the Twitter accounts linked and likely controlled by Incarcerated Bob.

He posted my home address, named a family member in a threatening tone, accused me of being affiliated with the KKK and added things like “we have investigators, as well” and “Stop now, my friend.”


Four days later, @IncarceratedBob tweeted the following (notice the hashtag):


A scan of the #Thinkonit hashtag archive on Twitter reveals Incarcerated Bob has used it frequently, including Monday in regards to Tim Tebow signing with the Patriots. Surely, just a coincidence, right?

But the bigger question is why would @BigEastProfit know criminal background checks were being performed on Louis Mendez? The increase in severity of the threats and the acknowledgement of the ongoing investigation were, at minimum, indications that I was on the right track.

The confirmation came a few days later from a financial executive and recreational sports bettor, who we’ll call Steve.

Steve had been on Twitter for only a short time, when he received a series of direct messages from @IncarceratedBob.

Steve had gotten off to a hot start with his picks on Twitter and quickly built a following of a few thousand followers. Incarcerated Bob saw an opportunity and offered Steve $10,000 to buy his account for six months. He tried to persuade Steve by telling him that his account only had value for a limited time

Incarcerated Bob gave Steve a phone number. It was the same number with the 347 area code that Louis Mendez used to register with the online sports book.

The two talked, but Steve declined the offer. Shortly after, a Twitter account with the exact same avatar as Steve’s and a slightly altered handle appeared. And the vicious attacks on Steve’s real Twitter account began.

Why even give him the publicity, other writers asked? Why put yourself through the harassment that comes from trying to interview Incarcerated Bob?

I considered it all and came up with a line of reasoning that is going to come off as overly dramatic and righteous, but here it is:

It started with a report that Floyd Mayweather bet $5.9 million on the Heat in Game 7 of the Eastern Conference Finals last Monday. The report was typical of Bob’s crew, completely unattributed. It came from his @Pregame_Steam account, which uses a logo of the sports betting site Pregame.com as its avatar. @Pregame_Steam is not affiliated with Pregame.com, according to company CEO R.J. Bell.

@Pregame_Steam also tweeted last Monday night that a $50,000 bet had been placed on the Heat -7 at the MGM sports book.


According to Jay Rood, Vice President of MGM Race and Sports, no such bet had been placed.

After being called out on their reports, the IBN crew has since begun reporting their make-believe big bets are occurring at offshore books. Their Vegas sources must have disappeared.

Despite the obvious and redundant signs of fraud, mainstream media outlets continue to treat the Incarcerated Bob Network as a legitimate source. The Mayweather bet is the most recent example. Some called @Pregame_Steam a Vegas site. Others were duped by the avatar and credited Pregame.com.

The Chicago Tribune ran an online report with the headline, “Vegas site claims Mayweather bet $6M on Heat.”

The article’s lead: “Boxing champion Floyd Mayweather is betting nearly $6 million on the Miami Heat to beat the Indiana Pacers in Game 7 of the Eastern Conference finals Monday night, according to pregame.com.”

The New York Daily News, the Daily Mail in the UK, Bleacher Report, FoxSports and many, many more outlets all published forms of the unsubstantiated rumor. Some were more cautious than others, but they all unknowingly helped fuel Incarcerated Bob’s persona and ego.

Incarcerated Bob uses these ridiculous, made-up reports to manipulate the media. He then uses the notoriety he receives to sucker sports bettors into buying picks from his handicappers. In doing so, he damages the credibility of my profession and the industry I cover. Plus, I feel bad for the naive bettors who are conned into believing Incarcerated Bob is something he’s not.

Look no further than the illegitimacy of Incarcerated Bob’s Twitter following for proof. As of Friday morning, 78 percent of his 105,000 followers were listed as fake, with another 12 percent inactive, according to fakers.statuspeople.com.


In addition, if you believe that @IncarceratedBob and @BigEastProfit are operated by the same person, as the above hashtag coincidence seems to indicate, then clients deserve an explanation for why they gave out opposite sides for Sunday’s Game 2 of NBA Finals.



I’m far from the only member of the media to be attacked by Incarcerated Bob. He’s relentlessly harassed ProFootballTalk’s Mike Florio, going as far as tweeting threats to Florio’s son. CBS Sports’ Jon Heyman also has been targeted. He’s taunted reality TV star Snooki and even went after the Ole Miss football program, including coach Hugh Freeze.

I mentioned to another media member and fellow victim of Incarcerated Bob’s attacks that Bob’s shtick was hurting our profession. His response, in my mind, solidified that I had to follow through on this story.

“There’s a lot of fun in this biz but it gets worse and worse every day,” he said.

He’s right. The media often deserves criticism, but it certainly doesn’t make our job easier, when we have people intentionally trying to deceive reporters with fabricated info. I felt that if I didn’t pursue this story, I was not doing my part to help the future of journalism and media. The bad guys are winning, I thought.

See, pretty damn dramatic and righteous, especially since all I really wanted was to interview Incarcerated Bob. I thought he deserved the chance to tell his side of the story.

All interview requests to Incarcerated Bob purposely were made through Twitter only. When he didn’t respond, I asked anyone who had purchased picks from Incarcerated Bob’s crew to reach out to me, adding that both positive and negative stories were welcome.

About a dozen emails came in, some with detailed tales of Bob’s handicappers trying to bilk clients out of money with things like unannounced commission fees after winning weeks. Others had screen shots of losing picks that evidently had been deleted or were not included in Bob’s handicapping records. Several who responded were embarrassed that they had fallen for the ploy.

“It’s inexcusable that someone with my level of education (I’m actually a real doctor, not just a silly twitter handle) would be so gullible,” one former client of the Incarcerated Bob crew wrote in an email. “But I was completely unfamiliar with twitter and never considered that someone could just create dozens of false extra personas to create positive reviews for a service. I also didn’t realize that tweets could be deleted (I was VERY unfamiliar with twitter) so I didn’t see how his record could be fake.”

Another former IBN client wrote: “I lost money with his plays. Especially bowl season. But it was cheap, so I couldn’t really complain. The worst thing about that set of guys is that they (make) 5 unit, 10 unit, 20 unit plays. But then they drop these 100 unit plays, and the guy taking my action has limits. I’m a college kid. So if I’m playing a $10 unit, I can bet $50, $100, $200, whatever. But $1,000? No way. Nobody I knows can afford to take that. And then they brag about how they went 2-1 but are +104 units on the day when the customers actually don’t have the ability to get down on that action. I probably learned the most valuable lesson of my young betting career from them, however. You can’t blindly tail picks. So I guess for that $90 bucks, I actually gained something, just not money I wanted.

There were a couple of positive responses, made exclusively on Twitter, from bettors who said they made money off of Incarcerated Bob’s network of handicappers.

Between threats, @BigEastProfit asked that I mention how Incarcerated Bob had donated to a random golf outing for a group of guys who were remembering a lost friend.

I also learned, though, that there were entire Twitter accounts dedicated to exposing Incarcerated Bob. It was all very telling, but not as incriminating as what happened last Tuesday.

Around 8 a.m., I received an email from Vanessa F., with the subject header “Randizzle Info.”

Vanessa F. bought picks from Randizzle, I thought? Hmmm …

The email read, “I may have something on Randizzle that will help out with the story your [sic] doing.

Please instruct me on how to get you the material.”

From my previous encounter with Bob’s crew, I quickly recognized the porous grammar in “the story your doing.”

Wary, I removed my phone numbers from my normal email signature line before replying to Vanessa F. If my suspicions were correct, I certainly didn’t want Vanessa F. to have my phone numbers. Altering my signature also would be a way to mark these emails in case something went astray.

A few hours later, things went astray.

This article appeared on Bob’s site last Tuesday morning. It concludes with a fabricated back-and-forth exchange with my email signature without my phone numbers.

“So I take it you’re declining the interview?” I tweeted to Bob after the story published. He cursed at me.

My goal of interviewing Incarcerated Bob was apparently dead.

In the end, Incarcerated Bob is a man, who lives by a unique set of ethics in an alternate reality that only he can understand. His worst crimes may very well be manipulating the media to sell picks, like plenty of unscrupulous sports handicapping sites do.

Perhaps this quote from Incarcerated Bob from a recent interview with Barstool New York’s KFC Radio best sums up this man: “I’ve been on Twitter, doing what I do on Twitter. I make a lot of enemies, which is actually good. People don’t understand the method to my madness. They get caught up in it. I’ve got guys, draft experts and all of these ESPN (guys going) ‘Ahhhhh, Incarcerated Bob.’ They get all uptight. Whatever, just keep talking about me.”

Wonder why Bob didn’t want me talking about him?

Note: I initially began reporting on this story for The Linemakers on Sporting News, but my editors and I agreed that it had escalated past content appropriate for that platform.

As a journalist, you never want to become the story, but, in this case, the best way to show how malicious Incarcerated Bob’s crew can be is by telling the story of what happened to me.

I considered pitching the story to other media outlets and having them independently report and write it, but ultimately decided that I didn’t want to subject anyone else to the backlash and harassment that is sure to follow.

I am confident in my reporting and believe this is a story that needs to be told.

If you’d like to help with this cause, please pass along this link or tell the story to members of the media—radio, online, TV and print—as well as any inexperienced sports bettors, so they do not get fooled by Incarcerated Bob and his army of goons.

David Purdum is a professional freelance writer. You can reach him on Twitter @DavidPurdum.

Compulsive gambling: Arnie Wexler stands behind those who can’t stop

I have covered the gaming industry for four years, writing hundreds of stories on pointspreads, big bets and long-shot parlays. Sadly, this is my first on gambling addiction. As a member of the media, I need to do more. Arnie Wexler already has.

By David Payne Purdum / @DavidPurdum

It was 1968 in North Bergen, N.J. Two grand bought a new car. Compulsive gambler Arnie Wexler was down $5K, approximately a year’s salary.

He was on his way to see the man.

Wexler, a 30-year-old plant manager for a Fortune 500 company, stepped inside his regular social club. He walked through the downstairs card room, where he had played in a Greek Rummy game full of “bookmakers and shylocks” since he was a teen.

Then, he headed up the stairs to Petey’s office.

Wexler had spent a lot of time in that office, which had a refrigerator, five telephones and minimal furniture. He had worked the phones and hooked up bettors with Petey for years. He received a cut of the players’ losses, but almost always gambled away any profits before he saw any.

Five months earlier, in November of 1967, Wexler had borrowed $5,000 from a loan shark, who also happened to be Petey’s brother. He had been paying $550 a month in interest, while making $125 a week. He was betting much more, sometimes on 50 games over a weekend.

Married with two kids, Wexler’s home life had fallen apart long ago. He had made three trips to the racetrack while his wife went through 37 hours of labor during the birth of their first child. With six outstanding loans, he’d look at his family, swear that he’d stop gambling then cry himself to sleep. The first thing he did when he woke up, however, was buy the daily racing form. When a bookie cut him off, he went straight home and sold the family car to a neighbor. It was one rock bottom after another.

But this particular April day was different. He entered Petey’s office, looked at his longtime bookie and told him that he was a compulsive gambler and was quitting.

Petey wasn’t buying it.

“He opened a drawer, and said, ‘I don’t care where the fuck you get the money,’ and pulled out a gun and gave it to me,” recalled Wexler.

It’s now been 44 years since Wexler last placed a bet.

On Opening Day of the 1968 baseball season, he put $20 on a two-team parlay. Bob Gibson and the St. Louis Cardinals cashed the first leg of his parlay. He needed Tom Seaver and the Mets to beat Juan Marichal and the Giants to cash.

“In the bottom of the ninth, the Giants came up with four runs and beat me,” Wexler said during a recent phone interview. “That was the last bet I ever made.”

Days later, he was in Petey’s office, contemplating the offer of the gun. Wexler left the gun there and came back to see Petey 10 straight days until he finally convinced him to take a $25-per-week payoff plan.

Fans of Arnie: From Oprah Winfrey to Howard Cosell

It was 1994. The phones kept ringing.

Wexler, who was head of the Council on Compulsive Gambling at the time, had just done the Oprah Winfrey Show.

He and his staff were manning six phone lines. They couldn’t keep up with all the calls from distressed gamblers looking for help. At the end of the day, the phone register showed 5,000 calls. By the end of the week, there had been 10,000.

Wexler wants to help them all, but admits keeping 1 of 10 clean is a lofty goal. But even now, the 74-year-old tries. He and his wife Shelia have trained approximately 40,000 casino employees on the signs of compulsive gambling. He blogs and sends out press releases about his story. He holds nothing back.

“Why do you open yourself up like this and admit these things publicly?” Howard Cosell once asked Wexler.

“The answer is I’ve been there,” Wexler replied. “I know what it does to people and that’s what helps me recover, opening myself up and be real about what I did with my life. But the real thing that I’ve done is the recovery piece.”

Arnie Wexler contact info. http://www.aswexler.com/

‘He’s saved a lot of lives’

I’ve been covering the gaming industry for four years. I’ve written hundreds of stories about big bets, line movements and crazy long shots. Sadly, this is my first about compulsive gambling.

“I am sure you have come in contact with lots of addicted gamblers and never knew it,” Wexler told me. “And they for sure would not tell you had the addiction; some may not have known it. Gambling is the invisible disease. There are no track marks, dilated pupils or the smell of alcohol. I’ve had judges refuse to acknowledge it.”

There is no debate that compulsive gambling can be destructive.

Popular sportstalk radio host Sid Rosenberg knows all about it. He’s struggled with compulsive gambling off and on and first met Wexler on a Friday night at a Gamblers Anonymous meeting in Boca Raton, Fla., sometime in the mid-1990s. They’ve been close friends ever since and stay in regular communication.

“The guy has saved a lot of lives, a lot of lives,” Rosenberg said of Wexler.

On July 12, it will be eight months since Rosenberg has placed a bet, he says. He credits Wexler in his recovery, but says he still plans on talking point spreads when he takes over the morning spot on WMEN-640 AM in August.

“I can’t stand those guys who used to smoke cigarettes, but now says he can’t stand them,” said Rosenberg. “I’ve been through about everything and don’t look down on people who use drugs or gamble. But I just can’t do it anymore. It’s caused my family a lot of heartache and a lot of money out the door … a lot of people knocking at my … it just caused my family a lot of heartache.”

Before our final phone interview, Wexler had just hung up with a concerned mother of a professional poker player. He has worked with several poker pros as the game’s popularity exploded in the last 10-15 years. This mother was particularly scared.

“This kid won a couple million dollars playing poker, but has a house in foreclosure in Florida,” said Wexler. “The last word he told his mother yesterday that he wanted to kill himself.”

Wexler’s voice quivered when he said it.

‘A special place in heaven’

Professional handicapper and Libertarian politician Wayne Root remembers meeting Wexler on a TV talk show in the late 1980s.

The two came from opposite sides of the gaming industry but became immediate friends.

“He is like an uncle to me,” Root said of Wexler in an email. “He is one of those special souls you meet just a few times in your years on this planet. There is a special place in Heaven for him.. Arnie cares for people with the worst gambling problems. No matter what they’ve done, no matter how bad they’ve been, Arnie is there for them. When you see something like that, how can you not help?”

Help is exactly what Root has done. He is one of the only—if not the only—professional pick seller who has a link to Wexler’s site and phone number for his gambling problem hotline listed on his own site, Winngedge.com. Root has also made numerous donations to Wexler’s cause.

“I built a wonderful career as a professional sports handicapper,” added Root. “And while 99 percent of my clients enjoy sports gambling and see it as a combination of entertainment and investment, it is a fact that some gamblers have addiction issues.

“Those of us who do well in this industry have an obligation to help that group,” he continued. “Arnie Wexler is the best in the world at doing that- because of his background (he’s been there) and because of his compassion. So I’ve always made it my obligation to donate to his cause and to be sure my clients knew that help existed if any of them should ever need it. That’s why the banner for Arnie’s organization has been on my homepage since the first day my site went up in 2000. And that’s why when Arnie called for financial help, I was always there.”

Q&A w/ Arnie Wexler

Q: What is the closest you’ve come to gambling in the last 44 years?
A: “I was speaking in Oklahoma City and was in a cab on the way to the hotel. I saw this sign that says, ‘Get your juices flowing.’ A new racetrack was opening. It showed a jockey on a horse, and I got juiced up just looking at this ad. We got to the hotel—I’m 20-25 years clean at the time—and ask where this racetrack is. And the doorman says, ‘It’s not open yet.’ “

Q: How many games were you betting at your peak?
A: Every game on the board. It wasn’t like I was smart enough to pick two or three games.

Q: What was the biggest bet you ever placed?
A: In December of 1967, I’m in a phonebooth in Queens. I put in the 10 cents to call the guy. I said, ‘Matty, I want to bet a 36-hundred-dollar round robin.’ The bet is $10,800. At that point, I’m making $90 to $100 a week. He says to me, ‘Arnie, don’t jerk me around. If you don’t have this money, don’t make this bet.’ I told him I had the money, but if I would have lost the dime in the phone booth, I couldn’t have called him back.

Q: Do you think you’ll ever place another bet?
A: I can’t answer that. I hope not. No one knows the answer to that question. I’ve seen too many experiences, people who’ve been clean for 20, 30 or 40 years, that go back to gambling. But I think I have enough protection in place that it shouldn’t happen to me.

Q: Your thoughts on Pete Rose?
A: I once did an ESPN special, “Should Pete Rose be in the Hall of Fame?” My take on it is, yeah, he should be in the Hall of Fame. But it’s his fault that he’s not in the Hall of Fame, because if he turned around and said, ‘Hey, I’m going to a 12-step program. I’m in recovery, and I’m not gambling anymore.’ I think he’d be in the Hall of Fame.”

Q: Tim Donaghy?
A: “When Tim got in trouble, we met twice and I helped him and got him in a 12-step program. I was in the court room for his sentencing and ended up sitting next to his father when he got sentenced. I was talking to Tim every week, but I’d say over the last six months we haven’t communicated much.”

Q: Nevin Shapiro?
A: “His lawyer contacted me several times and wanted me to don an evaluation on him, but it never happened. Six weeks later, I saw him getting sentenced.”

Roxy Roxborough: From dorm-room bookie to king of the Vegas point spread

By David Payne Purdum

It’s impossible to capture the sheer coolness of Roxy Roxborough’s life from a 30-minute phone interview and a few emails, but we’ll start on the campus of American University in the hippie days of 1969.

A dorm-room bookie with long red hair was sweating the World Series between the Miracle Mets and favored Baltimore Orioles. At the time, the Mets, a 1962 expansion team, had never finished higher than ninth in the 10-team National League.

The bookie offered the Mets at even money and got pounded by Long Island homers with bets ranging from $10 to $1,000. He had liability of $4,000 if the Mets won and a bankroll of $1,000.

“I couldn’t cover it,” Roxborough, the bookie, remembered, “but I wasn’t too worried about it, because I thought there’d be a spot to hedge somewhere in there. Besides, the Mets were considered pretty close to the worst team ever to make it a World Series.”

The Mets won in five games.

“I had to hold a press conference in the dorm to announce when I was going to pay,” he said with a chuckle. “So I went broke then. I had to borrow money to pay it off. I’ve never considered not paying in my life, so I had to borrow money. That probably set me back about a year, because I had to pay off the debt.”

It was a minor setback at the beginning of a legendary career that at its pinnacle had Roxborough positioned as one of the most influential people in sports. The founder of Las Vegas Sports Consultants from 1982 to 1999, Roxborough played all sides and always stayed a step ahead of the game. He taught a sports book management course at a local college, something he says undoubtedly made him a better oddsmaker. He also jumpstarted the “American Line,” a syndicated column that ran in a reported 120 newspapers.

“I remember him walking into the Royal Inn in the seventies with that long red hair,” said Jimmy Vaccaro, who rose to the top of the Vegas sports book scene at the same time as Roxborough. “We started talking and it didn’t take long to realize that he knew what he was talking about. He certainly did well for himself, and I admire him for that.”

Some might argue that Roxborough’s current life may be more enjoyable than the decades he spent as king of the Vegas point spread.

At 61 years wise, Roxborough spends the majority of his time in Bangkok now. He loves the food that fits his vegetarian lifestyle and has acquired a taste for fine scotch. He travels back to Vegas often and just took in the Kentucky Derby at the Wynn.

“People that say if you retire, you’ll get bored and won’t have anything to do are wrong,” said Roxborough. “I think the days go faster now; sometimes I don’t know where the time goes.”

He still dedicates some of his time betting on sports and pays close attention to the global industry.

“I play baseball futures, but that’s kind of limited on the amount you can bet,” he said. “Actually, the English Soccer League futures are probably the thing that you can get the world’s highest limits on. We get every game on cable, all 380 of them, so that’s the sport I follow.”

Roxborough works with a partner on his investments in baseball futures, trying to create his own markets by betting on teams to win divisions and the World Series. The frequency with which futures odds are updated by English bookmakers helps him control his positions.

“For some reason, English bookmakers are better at updating their NFL and MLB futures odds as the season progresses than U.S. bookmakers,” he said. “For example in the NFL, you can get a new set of regular-season wins and division prices updated each Tuesday.

“I think it’s an advantage for us,” he added, “because you put your opinion into the power rankings and feed that into the computer program and it plays out the rest of the season and gives you what the projected amount of wins is for the team.”

That’s not working out so well right now for Roxborough.

“We look all right on Kansas City under and Philadelphia under, but our big future bet is the Reds,” he said. “Our biggest position to win the division and World Series is on the Reds. And they’re underperforming right now.”