Grant Park—Chicago's Historic Frontyard—SOLD for Cash
- Aug 10
- 7 min read
By Don DeBat
First of two articles on the future of softball on Chicago’s lakefront.
While Rock music blasted from multiple stages during the recent epic “Lollapalooza” event, Grant Park’s historic and cherished 16-inch softball diamonds were trampled into utter destruction. Was this the final toll of the death knell for Grant Park softball?
By the fourth day of the Lollapalooza festival, on Sunday, August 2nd, the 2026 mega-event was marked by a sea of slurry, mud, monsoon rains and endless blasting music as 115,000 (mostly stoned) concert goers celebrated, and struggled to find space standing in the ankle-deep ooze.
With a total of 400,000-plus concert attendees over four days and nights, that’s a total of approximately 800,000 human feet trampling on Grant Park’s grass and softball diamonds.
While skinny dipping in Lake Michigan and free love wasn’t witnessed, the event was the equivalent of the famed 1969 Woodstock Music concert highlighting three days of peace and love held on Max Yasgur’s dairy farm in Bethel, N.Y.
Lollapalooze’s entertainment was mostly B-class bands. The event never even came close to Woodstock, which featured The Grateful Dead, Jefferson Airplane, The Who, Santana, Janis Joplin, Joan Baez, Sly and the Family Stones, and Jimi Hendrix.
By the end of the Lolla concert on Friday, a non-profit drug-control group, dubbed “This Must Be the Place,” had passed out 4,000 free doses of the opioid harm-reducer Naloxone from a booth on Grant Park grounds.
However, the aftermath leaves a lot of work for the producers of Lollapalooza to pay. Landscaping experts say Grant Park has a long way to go before it’s restored back to its old green self. In 2027, a mud-wrestling championship should be a post-concert event.
Last year, organizers spent more than $1 million on cleanup and restoration after Lollapalooza. This year’s costs will likely be higher after heavy rains over the weekend, said the organizer, “C3 Presents,” which must cover the costs of all resodding and labor. No problem. Gross revenue of $488 million was raised by C3 Presents.
Critics say the Chicago Park District now is about leasing public property for profit-making ventures. As a result, Grant Park, the place once dubbed “the city’s green front yard,” is off limits to the general public for half of the summer. Lollapalooza’s contract with the city of Chicago runs a whopping length of time—through 2032.
Is softball officially dead at Grant Park?
Meanwhile, die-hard Windy City softball players and fans say the desecration of the dozen pristine ball fields in Grant Park’s landmark “Valley”—between Balbo and Roosevelt Road east of Columbus Drive—may have put final nail in the coffin for “Chicago’s Game.” It is likely our beloved—16-inch softball is dead at Grant Park, which once was the biggest slow-pitch venue in the Windy City.
Downtown softball at Grant Park, where more than 350 teams once competed in leagues organized by the Chicago Park District, took a turn for the worse after the tragedy of 9/11. Metered parking along Columbus Drive near the fields was removed for security reasons. Players were forced to park five blocks away and walk to the fields, or take a cab.
Critics noted that the demise of softball at Grant Park really accelerated in 2022, when NASCAR, the redneck racing sport, got the green light on two years of racing.
Back in 2022, dozens of teams that have played in the corporate, industrial and saloon leagues at Grant Park for decades were tersely notified that their season had been canceled because of the upcoming June 22nd through July 5th NASCAR race, festivals and events.
“Mayor Lori Lightfoot and the Chicago Park District killed 16-inch softball in the Windy City,” said Ron Roenigk, publisher of Inside Publications, and a player-manager who participated in the Media Softball League for decades. Roenigk’s respected “Inside Dirt” team played at Grant Park, Lincoln Park, and Waveland Park on Tuesdays and Thursday nights.
“There are so many profit-making ‘close-off-the-park-to-non-payer’ events in Grant Park now that tax-paying Chicagoans have basically lost their recreational front yard for the better part of the summer. It really is a scandal,” said Roenigk.
The 70-year-old Media League shrunk to six teams in 2022 from 36 teams in 2019—an astounding 83% loss in the historic Chicago sport in just three years.
The softball teams being booted out of Grant Park were not playing for free. The annual league fee was $1,000 or more per team.
“Most Chicagoans don’t have any concept of how much public-park real estate the Park District has leased out to private companies involved in profit-making ventures,” Roenigk said.
“The Chicago Sport & Social Club, which bills itself as “a leader in the social-sports industry,” locks-up diamond permits early in the season, and that just reduces the days and times available for traditional Park District softball saloon leagues, which are rapidly disappearing. In this case, money talks, and if you pay enough money, you get preferential treatment from the Park District,” Roenigk said.
The organization’s website says Chicago Sport & Social Club (CSSC) is “the largest organizer of adult sports leagues, social events and tournaments nationwide. There currently more than 100,000 annual participants CSSC across 20 sports, including softball, flag football, kickball, beach volley ball, pickleball and cornhole, to name a few.
The Park District collects their cut of the fees, and provides diamonds. The CSSC organizes, administers and profits heavily from men’s and co-ed recreational and competitive softball leagues.
The CSSC play seven days a week in more than a dozen city parks, including Lincoln Park South, Revere, Hamlin, Stanton, Seward, Waveland, Union, Brands, Oz/Jonquil, Clarendon, Wrightwood, Welles, and Union.
CSSC leagues also are booked at the University of Illinois/Chicago Turf Recreation field, Whitney Young and Walter Payton high school fields.
For the 2026 season of seven games, each team pays an entry fee of $1,325. The fee includes team jerseys, an online schedule and standings, a certified umpire, and championship shirts for the winning team. Other perks and giveaways are handed out after the games in sponsor bars. Another bonus—a free Athletico Injury Assessment.
Historic game was born in 1887
“Grant Park’s historic softball fields should be nominated for landmark status,” noted softball umpire Larry Comstock, whose team, “Smoke”, was inducted in 2011 as a historic team in the Hall of Fame.
“After all, the very game of softball was invented here in Chicago in 1887, when the first indoor game was played at the Farragut Boat Club at Lake Park Ave. and 31st St., only a couple of miles from Grant Park,” said Comstock, who also played on the historic Chicago Sun-Times Hall of Fame team, inducted in 2008.
This writer was inducted into the softball Hall of Fame in 1999, played hundreds of games at Grant Park and won more than 30 championships in the Industrial League for the Chicago Daily News and the Sun-Times from 1975 through 1995.
As a player, manager, HOF inductee and life-long promoter of classic 16-inch slow-pitch softball, I am thoroughly shocked that “Chicago’s Game” has been driven out, and our public parks were sold for cash.
“With the Michigan Ave. high-rise cityscape to the west and Lake Michigan to the east, playing softball at Grant Park—Chicago’s beautiful front yard—always was an awesome experience,” recalled Robert Egan, a Chicago Sun-Times player and manager.
Egan organized and managed the Sun-Times tournament team and won the elite Mike Royko Classic Softball Tournament five times at the park in 2001, 2002, 2006, 2007 and 2009.
Egan was inducted into the HOF in 2008 along with 120 other Sun-Times and Daily News players as teammates on that historic team.
“Chicago’s clueless, Democratic-Socialist politicians are rewriting history, and spitting on the grave of famed columnist Mike Royko, a great promoter of the game,” Egan said.
Over the past decade, traditional men’s and women’s 16-inch softball saloon leagues have been shut down in far too many city parks to mention. At Lake Shore Park on Michigan Ave’s. Magnificent Mile, elite competition was played in the shadows of high-rises, and teams partied on Rush Street after games. Now, that only is a memory.
The once-elite 16-inch softball league at Clarendon Park, where the legendary “juiced ball” was mandatory in the 1960s by park director George Morris to hold scores down, now caters to 12-inch glove co-ed leagues in a “social setting”.
“Chicago’s game once was played in every park and gravel school yard across the city,” Egan recalled. “At the neighborhood level, serious and skilled blue-collar saloon teams flocked to corner taverns after the game for camaraderie—the life blood of softball.”
A tavern sponsor like Chicago Joe’s, a now-defunct saloon on Irving Park Road and Western, typically paid a sponsorship fee of about $600 per league to bring in the players for shots and beer, Egan said.
“Softball was good for neighborhood businesses, pumping tens of thousands of tax dollars into the city. Now, virtually all of the very competitive neighborhood leagues are dead and the bars are closing. It’s a very sad,” Egan said.
Paul Rowan, president of the 16-inch Chicago Softball Hall of Fame, noted that elite 16-inch suburban softball teams play at Forest Park and Westchester, and tournament action is starting to pick up again. This writer wishes them well. Keep cutting, dumping and pounding that Clincher.
For a good read on the history of softball in Chicago, buy a copy of “The Greatest Game on Dirt” by Al Maag. And, visit the 16-inch Softball Hall of Fame website:
NEXT WEEK: If Grant Park diamonds were razed and covered with Astro Turf for concerts, where should elite downtown softball leagues move?
For more softball and housing news, visit www.dondebat.biz. Don DeBat is co-author of “Escaping Condo Jail,” the ultimate survival guide for condominium living. Visit www.escapingcondojail.com. DeBat also is putting the finishing touches on “Chicago’s Game,” a book dedicated to 16-inch softball.
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