As most of you know from the advertising blitz, sports gambling went live in Missouri two weeks ago.
A DraftKings ad with the Gateway Arch…
A FanDuel ad with a family on their phones at Thanksgiving making a group parlay bet.
The path to legalized sports gambling in Missouri (and most states) has been a long one. Gambling on baseball goes back to the 1800s, and the top scandal came in 1919 when the “Black Sox” threw the World Series. Coincidentally, another traditional vice suffered a setback that year.
1919 – Booze and Prohibition: On January 16, 1919, the necessary three-fourths of the states ratified the 18th Amendment prohibiting alcohol.
Prohibition proved to be unpopular and lacked strong enforcement. Politicians and bootleggers kept the booze flowing in many cities, including Kansas City under its political boss, Tom Pendgergast. When asked how he justified ignoring Prohibition, Pendergast quipped, “The people are thirsty.”
Pendergast’s words can be seen today at Tom’s Town in the Crossroads (1701 Main).
Prohibition was repealed in 1933 upon ratification of the 21st Amendment.
1919 – Sports Gambling and the Black Sox: The 1919 World Series was thrown by several White Sox players who took money from a gambling syndicate and live in infamy as the “Black Sox.” Although gambling on baseball was common at the time, the game had avoided harmful public scandal. Now it had a black eye.
Team owners acted quickly to assure fans that the national pastime was not corrupt. Federal Judge Kenesaw Mountain Landis was hired as the first commissioner of baseball, and he promptly banned eight White Sox players even though they were acquitted of criminal charges. He said, “Regardless of the verdict of juries, no player who throws a ballgame, no player that undertakes or promises to throw a ballgame, no player that sits in conference with a bunch of crooked players and gamblers where the ways and means of throwing a game are discussed and promptly does not tell his club about it, will ever play professional baseball.” [See Landis (via actor John Anderson) deliver these lines as the players are celebrating their acquittal in the 1988 movie Eight Men Out (video here).]
Landis served from 1920 to 1944 and repeatedly dealt harshly with any player or owner associated with gambling. For decades, his successors did the same. Happy Chandler suspended Leo Durocher for a full season for consorting with gambling figures. Bowie Kuhn banned retired players Willie Mays and Mickey Mantle from any position in baseball because they were greeters at casinos. Peter Ueberroth, Bart Giamatti and Fay Vincent all played a role in the banning of Pete Rose for gambling.
In 1992, in the wake of scandals (e.g., Pete Rose) and the threatened spread of state-sponsored sports gambling, Congress passed the Professional and Amateur Sports Protection Act (PASPA). The legislation prohibited state-authorization of sports gambling. There were exceptions for existing operations (Nevada and sports lotteries in three states).
MLB Commissioner Fay Vincent was a strong proponent of PASPA and testified in favor of the legislation which protected MLB’s golden rule that baseball and gambling are incompatible.
Hold that thought.
Ken Burns and Daniel Okrent on Booze and Baseball: In 2011, the TV series Prohibition by Ken Burns and Lynn Novick was aired on PBS. It drew heavily on Daniel Okrent’s book Last Call: The Rise and Fall of Prohibition. I read Okrent’s book when it was published in 2010 and have recommended it often as a great primer of wedge issues in politics. Two powerful forces combined their efforts – women’s suffrage and the temperance movement. Each got an amendment to the Constitution.
The 19th Amendment remains in place – women still vote. But, as noted in Okrent’s book on the fall of Prohibition, “Through it all, Americans kept drinking, going to remarkably creative lengths to smuggle, conceal, and convivially imbibe their favorite intoxicants.” Or as succinctly stated by Tom Pendergast, “The people are thirsty.”
Okrent also appeared in several segments of the Burns/Novick PBS series Baseball (1994) and its update, The Tenth Inning (2010). His storied career in publishing, editing and writing includes two baseball books – The Ultimate Baseball Book (1979) and Nine Innings (1985). Among several positions, he was the first public editor of the New York Times, editor-at large of Time, managing editor of Life, and co-created a successful off-Broadway play, Old Jews Telling Jokes (Rita and I saw the play in NY in 2013; hilarious).
But as the polymath Okrent has said, the first line of his obituary will be that he invented Rotisserie League Baseball. In the 1979-80 offseason, at a lunch with fellow baseball fans at New York’s La Rotisserie Francaise, Okrent proposed the idea of a league where the fans would draft major leaguers and use official MLB stats to determine who fielded the best team for the season. The origin story was recounted by Okrent on the PBS series (3-minute video here).
Several of the Rotisserie League members were in the media, so the idea got good coverage. The game of “fantasy baseball” took off and spread to other sports and countries (e.g., soccer in Poland and cricket in the UK). Within a short time, millions were participating.
That’s not all Okrent did. In 1981, he wrote a profile of Bill James in Sports Illustrated. James, working in a warehouse in Lawrence, Kansas, had been self-publishing his annual Baseball Abstract since 1977. His subscriber base had grown from 75 to 2,600. Okrent saw the 1978 edition and was “stunned” by the “Sabermetrics” in the Baseball Abstract, a whole new way of looking at baseball statistics and player performance.
Okrent’s article won James a contract with Ballentine Books, and the first commercially distributed Baseball Abstract sold more than 100,000 copies. James became a star, and Sabermetrics was embraced by fans, sportswriters and organized baseball. So, Okrent not only succeeded in getting millions of fantasy fans to look closely at traditional stats (home runs, stolen bases, strikeouts, etc.), he also introduced them to the next generation of stats.
Fantasy Baseball – Skill or Gambling?: The participants in fantasy leagues normally pay an entry fee, and that money is pooled to pay off the winners. Most of the early fantasy leagues were groups of friends, but the lure of competing with bigger groups (and winning more money) led to national competitions. As an example, the 2025 NFBC (National Fantasy Baseball Championship) drew enough participants paying the $1,800 entry fee to pay a grand prize of $200,000 (not a typo).
Is this just a form of gambling? No. In most instances, fantasy sports are considered games of skill because they depend on a player’s research and management, not on an outcome determined mostly by chance (which is gambling).
Daily Fantasy Sports: Most early fantasy sports leagues began as season-long competitions. But why not more often? Say daily. Keep the action moving (like in gambling). So, daily fantasy sports (DFS) entered the mainstream led by major servicers FanDuel (2009) and DraftKings (2012).
MLB took notice. Fantasy sports leagues generate interest in the game. If done daily, even better. People who have a monetary interest in the outcome of a game are more likely to attend or watch on TV, both of which increase revenue for the teams.
DraftKings soon became MLB’s “Official Daily Fantasy Game.” During the Royals 2015 postseason, the games on TV were inundated with ads from DraftKings and FanDuel. They were in fierce competition to recruit players who would pay entry fees to participate in daily fantasy baseball. The long-term play was to convert these fantasy recruits to gamblers if the law changed to allow state-authorized gambling. It turned out to be a smart play.
The Gates (i.e., Betting Windows) Open: The money going into fantasy sports was substantial, but the real action and more betting options were available through illegal bookmakers. PASPA, the federal law banning state-authorized sports betting, had the effect of protecting bookmakers from state competition. To test the legality of PASPA, New Jersey authorized sports gambling in 2012. MLB and other sports organizations (pro and amateur) still staunchly supported PASPA and sued to invalidate New Jersey’s law. The suit was successful in the lower courts, but in May of 2018, the Supreme Court declared PASPA unconstitutional.
The Supreme Court decision was not a surprise. From Jane Leavy’s 2025 book Make Me Commissioner: “In 2017, the year before the Supreme Court made its decision…industry lobbyists met with MLB executives, cajoling them into joining forces with DraftKings and FanDuel…MLB considered its options and concluded it would be swell if betting companies were required to use the leagues’ proprietary data to set betting lines.”
It became a whole new ball game, and many states began the process of authorizing sports betting. The leagues, team owners and player unions adapted to the new legal landscape and made deals with gambling operators. When Missouri went live two weeks ago, it became the 39th state to offer sports betting.
DraftKings took on a new title: “Official Sports Betting Partner of MLB.” What would Commissioner Landis think?
From online and betting parlors to the mound and behind the plate.
The Vigorish: In illegal gambling, the bookie takes a cut (the vigorish) of the gambling dollars for brokering the wager (say 5-10%). The bookies set odds and spreads to achieve a balance of bets on each side, so they are not at risk on the outcome. The bettors win or lose, but the bookies always get their vigorish. [Exception: If there is a surge in betting for one side of a wager, the bookmaker may not have enough time to adjust the spread and correct the imbalance. This happened to the Kansas City mob when Chiefs fans overwhelmingly supported their team in Super Bowl IV in 1970. As the bookmakers scrambled to fix the issue, some big bosses got on phones wiretapped by the FBI. This provided evidence to link the mob to illegal gambling and unraveled other schemes, including a long-running operation to skim money from Las Vegas casinos. For the full story, see this excellent column by KCUR’s Dan Margolies and Sam Zeff.]
Legalization expands the pool of claimers to the vigorish, likely reducing the share of wagers going back to the winning bettors. The vigorish must be enough to pay (A) the state taxes on the wagering revenue and (B) the gaming operator’s profit and costs, which will include (i) the substantial advertising budget, (ii) payments to the leagues and teams for providing the platform for gambling (access to logos, data, etc.), and (iii) payments to the players unions for use of the players’ names and images.
New Competition – Prediction Market Loophole: The hot new item in the field is the prediction market, an exchange that offers trades of “event contracts” related to outcomes, such as elections, pop culture and now sports. The transactions are structured to be regulated by the Commodity Futures Trading Commission (CFTC). The Biden administration objected to the CFTC recognizing event contracts, but the Trump administration reversed that stance in early 2025. The first big player to go live under this format was Kalshi (which in January of this year hired Donald Trump Jr. as a strategic advisor).
The big advantage for an operator like Kalshi is that it is not subject to state regulation and so can operate in states that do not have sports gambling (e.g., CA, TX and GA). Lots of pent-up demand in those big states. Potential advantages include lower fees, no state taxes, more efficient markets/spreads, and crypto technology. This can translate to a lower vigorish and better payouts to the bettors.
Polymarket is another major prediction exchange, but it has only been operating offshore per an agreement with the Biden administration. A good explanation of their operation was recently on 60 Minutes (video here; and click here for the winner of $100,000 for picking the longshot of Pope Leo succeeding Pope Francis). Donald Trump Jr. became a member of the advisory board of Polymarket and invested in the company. Per Polymarket founder 27-year-old Shayne Coplan, “This [administration] is very pro-innovation, and pro-crypto, and pro-Polymarket, which is amazing.”
The existing fantasy/gambling companies are also racing to join the prediction format. For example, Underdog Sports had planned to operate in Missouri as the gambling partner for the Kansas City Royals, but it cancelled the deal to focus its business efforts on the less-regulated prediction markets. The top two gambling operators are also making the move (at least in states without current gambling), and this is creating some friction in the industry. From the Washington Post: “Two of the biggest names in sports gambling, DraftKings and FanDuel, left the American Gaming Association, the powerful trade group representing the casino and gaming industry. The split underscores the widening rift over the fast-growing world of prediction markets, a form of real-money trading that blurs the line between gambling and financial speculation.”
And the legal battle is not over. Several legal challenges are pending on whether prediction markets constitute sports betting that is subject to regulation (and taxation) by the states. Stay tuned.
The People Are Thirsty: I’m sure Daniel Okrent did not anticipate his Rotisserie League would start a chain of events that led to the big business of legalized sports gambling. From Jane Leavy’s Make Me Commissioner:
“Rotisserie begat fantasy games sponsored by ESPN and Sports Illustrated, CBS and Yahoo, which begat mega fantasy site DraftKings, which became the ‘Official Daily Fantasy Game’ of Major League Baseball in 2013, which led to what is now known as the Daily Fantasy Sports (DFS) industry…[leading] to 62.5 million North Americans who competed in daily fantasy sports (DFS) in 2022, 81% of whom also gambled on sports.”
Just like liquor during Prohibition, sports gambling did not disappear after the Black Sox scandal. It just continued underground in its own version of a speakeasy world. It inched its way into the open with daily fantasy sports and then became too profitable for states and leagues to not ask for their share. The demand from gamblers is so strong that the company value of each of the four biggest operations exceeds $10 billion (Kalshi, Polymarket, DraftKings and FanDuel). With that much money flowing, it’s not going away.
Trouble will arise from the ubiquitous availability and ease of placing bets on the phone. For example: (i) Increased gambling addiction (as warned in all the ads); (ii) social media harassment of players (who don’t satisfy a “prop” bet established by the gambling operator, like not hitting a home run in a game or a pitcher falling short on an over/under strikeout bet); and (iii) scandals (there have already been two MLB players suspended over fixing prop bets). Similar arguments were made about booze in the Prohibition era. The concerns are legitimate, and those involved should use their best efforts to minimize the negative factors.
In the end, the human nature lesson was given to us long ago by philosopher Tom Pendergast. He was talking about booze, but it also applies to gambling.
“The people are thirsty.”
Above, Tom Pendergast and his poker-playing and bourbon-drinking political protege Harry Truman. Hopefully, most will follow Truman’s example of drinking and gambling in moderation (if at all).
Lonnie’s Jukebox – Gambling Songs: I don’t know any popular songs about sports gambling (probably too soon), so I’ll go with dice and card games.
“Stagger Lee” by Lloyd Price. I bought this record when I was in high school. “It was Stagger Lee and Billy/Two men who gambled late/Stagger Lee threw seven/Billy swore that he threw eight…Stagger Lee shot Billy…so bad…the bullet came through Billy and broke the bartender’s glass.”
“Ramblin’ Gamblin’ Man” by Bob Seger. “Learned to spin fortune wheels and throw dice…I got to ramble/I got to gamble.”
“Rambling, Gambling Willie” by Bob Dylan. I accidentally ran into this video when I was looking for Bob Seger’s song. It was new to me, so I checked in with Hot Stove’s Bob Dylan Editor, Steve Paul. Steve says the song was recorded for The Freewheelin’ Bob Dylan album (1962) but was dropped. The outtake survived and became part of some of Dylan’s bootleg sets, including the one just released in October, Through the Open Window. According to the singer’s website, Dylan has never performed the song in concert.
In the song, Willie rambles so much that he has 27 children and no wives. But he has a heart of gold and supports all the families with gambling winnings taken from riverboats, mining towns, railroad yards, etc. After years of success, a sore loser shoots Willie, and when Willie’s cards fall to the floor, they are aces backed with eights (the “dead man’s hand” of Wild Bill Hickok).
“When You’re Hot, You’re Hot” by Jerry Reed. “Had a big crap game goin’ back in the alley/And I kept rolling’ them sevens and winnin’ all them pots/My luck was so good, I could do no wrong/I just kept on rollin’ and controllin’ them bones.”
“Big Bad Leroy Brown” by Jim Croce. While shooting dice, gambler Leroy Brown cast his eyes on the wife of jealous man. “Well, the two men took to fighting/And when they pulled them from the floor/Leroy looked like a jigsaw puzzle/With a couple of pieces gone.”
“Tumbling Dice” by the Rolling Stones. A metaphorical mix of a restless gambler’s dice game and the unpredictability of romance.
“Tumbling Dice” by Linda Ronstadt. Mick Jagger thought Linda should do more rock ‘n’ roll songs and suggested she record this song. She did but flipped the perspective to the female side by changing the opening lyrics. The link is to her performance of the song in the 1978 movie FM. I think it’s better than the Stones. But I’m biased when it comes to Linda. Below, Linda and Mick.
“Luck Be a Lady” by Frank Sinatra. From the 1950 Broadway show Guys and Dolls. The song is performed by character Sky Masterson, a gambler rolling the dice on a high-risk bet.
“The House of the Rising Sun” by the Animals: The setting for this traditional folk song is often thought to be a brothel. This is especially true when sung by a female, say Dolly Parton (her version here), who finds that the “House” has “been the ruin of many a good girl/And oh God, you know I’m one.” Eric Burdon of the Animals changed “good girl” to “poor boy,” and he has said that the song can apply to any temptation or other poor life choice (like his father being a “gamblin’ man”). There was no ambiguity at Rick’s Cafe in Casablanca (video here)…
“The Gambler” by Kenny Rogers. “You got to know when to hold ‘em, know when to fold ‘em…”
One famous poker player who did not always follow the rule of “know when to fold ‘em” was Harry Truman. He would often stay in a game with a poor hand because he enjoyed the game and his friends so much. In the early 1930s, per David McCullough’s epic Truman, Judge Harry Truman had a regular Monday night poker game near the courthouse on the Independence Square. “The game had a 10-cent limit. A little beer or bourbon was consumed, Prohibition notwithstanding.” Truman continued playing poker through his presidency and retirement years. Truman borrowed from a poker expression (“pass the buck”) to popularize the phrase “The buck stops here,” his commitment to accept responsibility for his decisions rather than shift blame.
“Viva Las Vegas” by Elvis Presley. The King’s anthem for Las Vegas. Link shows clips from film of the same name. “Oh, there’s blackjack and poker and the roulette wheel…And your one-arm bandits crashing…Lady luck please let the dice stay hot/Let me shoot a seven with every shot.”
Walk-Off Story – Home Run Derby: My personal sports betting is limited to putting in $75 each year to participate in a fantasy home run derby. We have ten participants who each draft eight players. Up to three moves can be made during the season to replace injured or poorly performing players.
Standings are sent out weekly by the commissioner. This season’s commissioner was Tim Sear who earned the position by coming in last in 2024. Tim quickly exercised his executive power to give our contest a new name: Roberto Clemente Home Run Derby. Tim is famous for his idolizing of “The Great One” (Hot Stove #262).
As for this 2025 season, the winner was…Tim Sear. Nice comeback. Last to first. Yesterday, Tim graciously (ha!) accepted the traveling trophy at our awards breakfast at Niecie’s Restaurant. Here’s the crew:
At the bottom right, as last year’s winner, I am handing the traveling trophy to Tim Sear. Counterclockwise from me: Jeb Bayer, David Matson (in from Portland, OR), Tom Grimaldi, Bob White, Tim Sear, Jim Heeter (in from Boulder, CO) and Steve Roling. Not pictured: Joel Poole (Columbia, MO) and Todd Poole (Portland, OR).
The top five this year (and the number of homers):
Tim Sear (247)
Lonnie Shalton (241)
Steve Roling (220)
David Matson (218)
Todd Hoppe (217)
Cash prizes go to the top three players. There is also a prize for the best 8th round draft pick, won by David Matson (James Wood, 31 homers). The honor of being commissioner next year goes to Jeb Bayer (184 homers).
Todd Hoppe is another story. Three years ago, one of our players retired from the league. David Matson suggested his son-in-law Todd Hoppe as a replacement. Todd won the first year he played. Matson was accused (in a friendly manner) of bringing in a ringer. But Todd did not repeat in 2024 and finished out of the money in 2025 in 5th place.
But don’t feel bad for Todd. Remember the national fantasy league competition discussed earlier in this post? Todd was one of the players who paid in $1,800 to participate.
Todd won the grand prize! Yes, the 5th place finisher in the Roberto Clemente Home Run Derby came in first in the NFBC Main Event. $200,000! Not a typo. Details here, including Todd’s original roster and his free agent pickups during the season. A superb example of skill, not chance.
Congratulations Todd!!!
Walk-Off Photo – Loose Park 2025: We got a nice surprise last Tuesday. The temperature hit 54 degrees, just enough to get us out for a walk in Loose Park. Probably the last time for 2025.
The photo below is not from last week. It’s from a day in August when the temperature was so high that we walked before breakfast. Sunrise at the Rose Garden.
See you in 2026.
Happy Holidays!!!