Dollars and sense: It won’t be like Lane’s Lounge, but gambling is coming to Chicago (2024)

Dollars and sense is a regular column about Chicago sports media and business.

In the days after the Illinois legislature set the table for Gov. J.B. Pritzker to officially welcome in legal sports gambling to Illinois, I reached out to our five major sports teams for comment. I wanted to talk to owners or top executives about their excitement (or even their reticence) about a near-future where fans can not only legally bet on sporting events, but place the bets at the actual stadium they’re watching a game in.


There will be a lot of pie to be divvied up in the coming years, as people love to lose money gambling on sports. Trust me, I know from experience.

Years ago, my creative writing professor at the University of Chicago, a wonderful writer named Dan Raeburn (buy his memoir here), shared some cribbed wisdom with me that many gamblers (the common joes, not the pros) really chase the feeling of losing more than they do winning. It’s a difficult concept to square — because winning a bet is awesome — but he’s not wrong.

With that in mind, you know Chicago’s sports teams are dying to make more money off their fans. They’re already getting them drunk at (at least) $10 a pour, why not get a little more through gambling? Several teams had representatives in Springfield, Ill., and sports leagues made their presence known as well. While there isn’t any outrageous cut going to the leagues, they’ll make their money by doing business with sports books.

Alas, no one from the Cubs, White Sox, Bulls, Blackhawks or Bears wanted to talk on the record about the gambling bill. Not until everything was official. I did chat with one team representative on background and he assured me of the obvious: yes, his team would be interested in making more money. With a cut from an onsite sports book and an expected influx of advertising, each team should make a little coin from the new law. Plus, as we know, gambling keeps fans engaged during otherwise less-meaningful games.

Last Tuesday, Cubs manager Joe Maddon was asked about legalized sports betting, and said he was a little “surprised” by the decision, considering the history of gambling and sports, particularly baseball. Obviously, Chicago was at the epicenter of the most famous gambling scandal in sports 100 years ago.

But with legalized gambling, big bets would be monitored, thus reducing the chance for game-fixing and corruption. Though there will always be an exploitable black market for gambling, and given that the new law won’t include in-state college athletes, that’s an area to still watch.

Dollars and sense: It won’t be like Lane’s Lounge, but gambling is coming to Chicago (1)

Get ready to stare at big boards in Illinois casinos, racetracks and sports books. (John Locher/AP Photo)

Maddon and I hail from similar hometowns. He’s from coal country in eastern Pennsylvania and I grew up across the western Pennsylvania border in Eastern Ohio.

Gambling was prevalent in my hometown, going way back. Arguably the two most famous people from my hometown are Jimmy “The Greek” Snyder and Dean Martin, if that says anything.


Maddon’s face brightened when I asked him what the gambling scene in Hazleton was like.

“Tremendous,” he said. “Bellhops backroom, anything you wanted. Actually, Uncle Carly’s Third Base Luncheonette on Saturday night, that would be the big poker game. And even Monsignor Rosario would be there like at 5 or 6 o’clock in the morning. So you would go up there on a Sunday morning after church and they’d still be playing in the backroom and it would be smoky. Little room, as big as my office, maybe, with one of those round tables with a nice leather top to it. Action everywhere, man. They had the daily number, you could get it anywhere in town. It was awesome. Awesome.”

As someone who regularly bet $11 parlays (the $1 was the juice) as a high schooler at Lane’s Lounge, a cigar store that didn’t sell many cigars in Mingo Junction, Ohio, as well as the apartment of an old bookie named “Stinky Fred,” I could appreciate Maddon’s recollections. (Man, I loved Lane’s Lounge. You should’ve been there.)

What will legalized gambling do for American sports? Mostly it takes away unnecessary red tape. And don’t forget, there was a time, not that long ago actually, when the NFL didn’t endorse fantasy football. Now the NFL recognizes its benefit.

Are there downsides? Of course. Plenty of people suffer from gambling addictions or predilections. But it’s already easy to gamble online, now it will just be easier to collect. (The easiest way to bet for many hardcore gamblers will still be their local bookies.)

Famed local gambling writer/broadcaster Joe Ostrowski (who moonlighted as a gambling writer for us last football season) has been all over this story and decamped to Springfield for the final days of the legislative session.

You should listen to his podcast here, where he outlined some answers to FAQs, like whether existing racetracks, casinos and professional sports venues (of a predetermined size) can get sports book licenses.


Mobile betting is the key to making serious money for the state (and less importantly, the sports book owners), but the wrinkle there is you have to register for a mobile account at an actual sports book. That’s an inconvenience that will surely limit participation.

To put that in perspective, when I went to cover the Bears game at the Giants last winter, I downloaded one of the apps (FanDuel or DraftKings, I honestly can’t remember which) in advance and when I landed in Newark, I put money in the account and placed some bets. This was all for research purposes, of course. I never had to set foot at the FanDuel sports book at the Meadowlands and I got money out easily (though it took a week to process).

One thing I learned from Ostrowski’s show was that there’s also going to be a sports wagering program available at licensed lottery retailers, like 7-11. Essentially you’ll only be able to bet parlays there, but that’s still very fun. Growing up we had parlay cards at convenience stores. They benefitted local sports leagues. Or so we were told.

Illinois will be the first state to allow sports books inside stadiums and arenas, so you have to imagine that you’ll see them pop up at the United Center and both baseball stadiums by 2020, at least. Soldier Field will be an interesting story because it’s not owned by the Bears and the NFL runs itself differently than the other leagues.

No one is sure when the sports books will go up. Ostrowski said people in the know are guessing either before football season or around Super Bowl time.

Dollars and sense: It won’t be like Lane’s Lounge, but gambling is coming to Chicago (2)

For a time in the late 1990s, there were two quasi-legal sports books on this street in Mingo Junction, Ohio. (Michael S. Williamson/The Washington Post via Getty Images)

While this new law will give a little sugar to the pro teams, it should be a godsend to struggling race tracks in lllinois that have been fighting for table games for years. One would hope it will increase the small purses at horse races that are hurting the tracks. That might be bad news for Johnny Morris, who likes his space at Arlington Park.

In interviews with The Score and The Athletic before the bill was passed, Cubs president of business operations Crane Kenney talked about a complementary gambling-focused broadcast for Cubs games.


“That’s out there,” Kenney said of his Score interview during a subsequent sitdown withThe Athletic. “It was just legalized in Iowa, which is a part of our territory, and I believe it happens here. (With an) audience that really cares about gambling, you have a chance to serve them in a different way. You’re seeing Ted Leonsis doing this with the Caps and the Wizards in Washington.

“Even in our national games, you’re seeing it’s not a gambling feed, but it’s more data and probabilities, stolen-base probability, more information as a starter gets later in the game, second time through the order, third time through the order, how the probabilities are all changing. They’re not actually doing that to try and entice a gambler to make a wager because it’s not legal in most states. But you can already see how the game production has changed a little bit to be more stat-driven.

“I think the question was asked to me: ‘Could you ever see a feed that’s really dedicated to the gambler?’ And my answer is ‘yes.’ I think somewhere – I don’t know when – but somewhere down the road there’s the same trucks, same production, with maybe a different booth and a different conversation with a group of fans.

“To reach some of those younger fans that may have a different ear for the game and are looking for a different type of production – I think you could probably see that down the road.”

If I could go back and time and tell a teenage Jon Greenberg that he’d be a sportswriter in Chicago and gambling and weed were being legalized, he would, well, hopefully take a look at his older self and start working out more.

He’ll show us

I reviewed “Pooh,” the Derrick Rose movie, of which Derrick Rose is listed as a producer, a few months ago, and now it’s time for another Derrick Rose piece of journalism, an autobiography titled “I’ll Show You,” written in his words by the great Sam Smith.

Smith, who had a good rapport with Rose during his Bulls career, told me he’s not done editing it yet and I gave him some suggestions (mostly organization-related) after quickly reading the slim book, but as someone who has interviewed Rose many times over the years, I really felt like Rose was talking to me. That meant some funny stories and some head-scratching logic. I both learned a lot about Rose and had some of my observations confirmed. Derrick Rose fans will love this book and his critics probably won’t read it.


I’ll write about the book in more detail before it is released in September.

Hey, I wrote a book too

If you haven’t muted me yet on Twitter, you know that I wrote a book about the Cubs. It’s out now and you should definitely buy multiple copies. This book was a bit of a rush job (I didn’t agree to do it until late June 2018), though I hope it doesn’t show in the prose.

It goes from the 2003 offseason through the early months of 2019. It does not contain the Craig Kimbrel signing, alas.

During one of my TV interviews for the book, WCIU’s Jon Hansen said he thinks it’s a perfect primer for new Cubs fans to catch up on recent history. I agree.

Thanks to @TheJamTVShow for having me on!

— jon greenberg (@jon_greenberg) June 6, 2019

Writing a book in short order (I turned in my manuscript in late December and we edited throughout the next couple months) was a challenging but rewarding experience. And now I’m thinking of what my second book should be about.

Come catch me on my book tour this summer. This is how it looks so far.

June 10: Barbara’s Bookstore 111 N. State St., Chicago, 5 p.m.

June 26: Midway Lit Fest at Midway Airport from 11 a.m. to 2 p.m.

July 11: The Book Stall, 811 Elm St., Winnetka, 6:30 p.m.

July 25: The History Center of Lake Forest/Lake Bluff, 509 E Deerpath Rd., Lake Forest, 7 p.m.

Aug. 7: Barnes & Noble, 728 N. Waukegan Rd., Deerfield, 6 p.m.

Aug. 21: Standard Club, 320 S Plymouth Ct, Chicago from 12 to 2 p.m. (part of a lunch series)

News and notes

I’ll never be able to do a quick hits section quite like the Daily Herald’s Jim O’Donnell, but I have a few things from my notebook. … If you read about ESPN 1000 protesting Nielsen’s ratings and being proven correct, with a small overall gain, I got some numbers from that recent April do-over and they show WMVP’s David Kaplan easily beating The Score’s Dan Bernstein and Connor McKnight in the major demos, among other gains. What do those numbers really mean? Who knows? I don’t trust them, corrected or otherwise, and too many people use these opaque ratings as a scoreboard. Both stations are worth listening to, in my opinion, and some shows are better than others depending on the day and the guests. And the numbers will probably reverse themselves in June. … I’m told that picture of Kapper’s “company” on his streaming link is about to become a little more outdated. And isn’t it past time to superimpose Pat Boyle on there? Who else should join Kap’s coterie of co-hosts? … We’re covering the Chicago Sky now and you should definitely be following ace writer Maggie Hendricks.The Sky have struggled to gain a foothold in Chicago for a variety of reasons, mostly that they don’t win enough to win over average sports fans. (They’ve also moved buildings three times, play in the summer in a city with two baseball teams, play in a league that underpays its talented players so bad they have to play year-round, etc.) One thing the Sky should do right now is make more of a push to get their players on more local TV and radio shows. Running commercials for games is meaningless when fans don’t know the players. Why not have Stefanie Dolson on SportsTalk Live? Or Diamond DeShields on The Score? The Sky had a real star in Elena Delle Donne, but never capitalized on it in terms of interest (I think they got their most social media attention when Dan “Barstool Big Cat” Katz would go to games in a tight jersey) and now she’s gone. They should be more proactive in getting their best players in front of fans. … I was going to write a whole thing on this, but it’s too dumb. Still, my 8-year-old son reminded me again this weekend of the time I got scammed on Craigslist for tickets. In the months since, when I’ve told him we’re going to a game, he always goes, “Are you sure you have tickets?” It was a Bulls game this past winter, a Sunday day game, and I was in a rush and I made the mistake of being too thrifty and looking for a deal on 200-level tickets. I actually got scammed twice in a period of 15 minutes, sending money to people who then went dark. I did get my money back on the PayPal transaction, but not from the CashApp one. The seller deleted his account and the company dodged my emails. My lesson to you: Don’t use CashApp unless it’s with your friends. And don’t be an idiot and use Craigslist for tickets.

(Top photo: Ethan Miller/Getty Images)

Dollars and sense: It won’t be like Lane’s Lounge, but gambling is coming to Chicago (2024)


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