Opinion Columnist
Tom Hennessey
Tom Hennessey has been writing his column, “Hennessey’s Take,” for The Windy City Dispatch since 1996. A lifelong Bridgeport resident, he’s covered everything from aldermanic scandals to the great ketchup debates, always with the kind of blunt honesty that makes editors nervous and readers loyal. He has never once used the word “vibes” in print and intends to keep it that way.
When he’s not filing copy from his usual booth at Schaller’s Pump, Tom can be found arguing with his neighbors about the proper way to shovel a sidewalk or writing strongly worded letters to the CTA. He is the author of three unpublished novels and the proud owner of a 1994 Ford Taurus that he insists “runs fine.”
Articles by Tom Hennessey
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OPINIONMarch Weather Recap: Chicago Experienced All Four Seasons on 17 Separate Days
Meteorologists confirm that March 2026 delivered summer, winter, fall, and spring conditions on more than half its calendar days, sometimes within the same afternoon.
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NEWSCulpepper Terminated a Record Fourth Time After Rearranging Entire Newsroom According to Feng Shui
Dennis Culpepper, who has now been hired and fired four times in a single month, was let go after reorganizing all desks, filing cabinets, and the managing editor's office to optimize the building's 'chi flow.'
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LIFESTYLERivers Restaurant Closing After 30 Years, Leaving Loop Traders With Nowhere to Discuss Futures Contracts Over Salmon
The riverfront institution at 30 S. Wacker Drive will serve its final lunch April 12, ending three decades of power meals, client dinners, and overpriced wine within walking distance of the CME.
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OPINIONThe White Sox Lost 14-2 on Opening Day and Struck Out Twenty Times and I Need Everyone to Understand What That Means
Tom Hennessey watched Chicago's other baseball team play their first game of the season. He has feelings.
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OPINIONI Watched the Bulls Give Up 157 Points Last Night and I Have Some Thoughts
Tom Hennessey sat down to watch some basketball. He is still processing.
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OPINIONBridgeport Man's Dibs Collection Now Exceeds Available Parking Spots on His Block
Walter Novak has placed 14 chairs across 11 parking spots he claims to have shoveled at various points during the last three winters.
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NEWSWell. There It Is.
Tom Hennessey had just finished writing that he wasn't getting his hopes up when the Cubs went out and lost 10-4 to the Nationals on Opening Day.
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NEWSI Told Myself I Wasn't Getting Excited About the Cubs This Year
Lifelong fan Tom Hennessey recounts his annual vow of detachment, and exactly when it collapsed.
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OPINIONBears Spend Entire Free Agency Period Buying Things, Fans Cautiously Optimistic for First Time Since Last Time
Ryan Poles has signed a safety, a linebacker, a defensive tackle, and traded for a center, prompting Bears fans to enter the most dangerous phase of the offseason: genuine hope.
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OPINIONChicago Fire Win Consecutive Games, Confuse Entire City
Hugo Cuypers has scored in four straight matches and the Fire look genuinely competitive, leaving fans unsure whether to celebrate or check for signs of an elaborate prank.
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OPINIONLogan Square Board Game Night Ends in Schism Over Settlers of Catan Trade Embargo
What began as a friendly Thursday gathering has fractured into two rival factions that now meet on alternating weeks.
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OPINIONBulls Front Office Reportedly Alarmed After Team Accidentally Wins Four Games in March
After an 0-11 February that had the tank running smoothly, Chicago's basketball team has inexplicably won four games this month, threatening the franchise's carefully cultivated losing strategy.
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OPINIONEveryone Left for Spring Break and Frankly the City Has Never Been Better
With CPS on vacation and half the city decamped to warmer climates, one columnist reports that Chicago has achieved a state of grace he did not know was possible.
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OPINIONHennessey's Take: The Blackhawks Beat Minnesota and I Don't Know What to Do With My Hands
After 19 consecutive losses to the Wild stretching back to 2019, the Blackhawks finally won, and one columnist is not emotionally prepared for it.
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OPINIONHennessey's Take: I Voted on Tuesday and All I Got Was This Lousy Democracy
Tom Hennessey reflects on the Illinois primary, the death of the simple ballot, and why he misses the days when you could vote in under ten minutes and still make it to Schaller's by noon.
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OPINIONUnited Center Begins March Madness Conversion; Bulls Fans Reminded the Building Has Other Uses
With the NCAA Midwest Regional arriving March 27, the United Center is undergoing its annual identity crisis: a hockey-and-basketball arena that must briefly become a different kind of basketball arena.
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OPINIONWhite Sox Catcher Pulls Hamstring Playing for Italy; Sox Fans Unsure If This Counts as Their Problem
Kyle Teel's 4-to-6-week injury in the World Baseball Classic has prompted an existential debate on the South Side about whether suffering for another country's flag still qualifies as White Sox suffering.
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OPINIONIllinois Gets a 3-Seed and Now Every Person I Know Is a Basketball Strategist
The Illini's sixth consecutive NCAA Tournament appearance has transformed a city of nine million Bears opinions into a city of nine million bracket analysts, none of whom watched a regular season game.
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OPINIONMy White Sox Catcher Helped Italy Beat America in the World Baseball Classic and Then Got Hurt Doing It
Kyle Teel, the White Sox's top catching prospect, played for Team Italy in its upset of Team USA, strained his hamstring in the process, and will likely miss the start of the season — a sequence of events that Tom Hennessey is processing in real time.
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OPINIONMarch in Chicago Has Become a Month-Long Emergency and I Would Like It to Stop
Between Pulaski Day, Daylight Saving, tornadoes, Pi Day, St. Patrick's Day, the primary election, and spring training, Tom Hennessey would like to know when he is allowed to simply exist without an obligation.
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OPINIONI Have Watched the River Turn Green 31 Times and I Have One Simple Request
Tom Hennessey on what St. Patrick's Day used to be before it became a content opportunity for people who discovered Chicago six months ago.
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OPINIONI Watched Alex Bregman Take Batting Practice and Now I Need Everyone to Calm Down, Including Myself
Tom Hennessey travels to Sloan Park in Mesa, Arizona to see what $175 million buys you in a Cubs uniform, and returns with feelings he is not fully prepared to process.
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NEWSBears Spend $70 Million on Defense, Remain Philosophically Committed to Offense as Concept
The Chicago Bears signed two defensive starters in a $70 million spending spree this week, completing a free agency period in which the team acquired zero wide receivers and confirmed, once again, that they have a plan.
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NEWSThe White Sox Open in 16 Days and I've Already Bought My Tickets, Don't Ask Me to Explain Myself
With the 2026 season opener set for March 26, Tom Hennessey delivers a full accounting of his feelings about the White Sox rebuild — which amounts to a grudging, eyes-open, completely irrational kind of hope.
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NEWSCubs Lose Spring Training Game 9-5; Fans Activate Annual 'Doesn't Count' Protocol Right on Schedule
The Chicago Cubs fell to the San Francisco Giants 9-5 in Scottsdale on Sunday, a result that the franchise's fanbase has officially designated as 'informational rather than meaningful,' 'too early to say anything about,' and 'actually kind of encouraging if you look at it right.'
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NEWSChicago Hits 54 Degrees Saturday; City Declares It Summer, Opens Everything, Refuses to Discuss March
A high of 54°F arrived in Chicago Saturday, prompting the immediate deployment of patio furniture, the first shirtless jogger sighting of the calendar year, and a collective agreement among residents that this is, for all relevant purposes, warm.
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NEWSBears Trade DJ Moore to Buffalo, Confirm They Have a Plan, Won't Say What It Is
The Chicago Bears sent wide receiver DJ Moore to the Buffalo Bills Thursday for a second-round pick, freeing up $16.5 million in cap space and adding to the team's growing collection of draft assets, future hope, and the comfortable uncertainty that has defined Chicago football since approximately forever.
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OPINIONIndiana Tries to Woo the Bears; Chicago Responds By Pretending Indiana Didn't Say Anything
Indiana lawmakers have rushed through proposals to lure the Chicago Bears across state lines, prompting a masterclass in the Chicago tradition of ignoring an overture so completely that the person making it begins to question their own existence.
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NEWSCity Officials Pitch Bears Stadium Again, As God Intended, For the Millionth Time
Governor Pritzker and Mayor Johnson continued pushing for a new lakefront Bears stadium this week, marking what historians estimate is the 4,000th consecutive week someone in a suit has pointed at a rendering of this building.
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OPINIONThree Illinois Congressmen Quietly Ask Their Districts to 'Hold On' While They Chase Senate Seat
With U.S. Sen. Dick Durbin retiring, three sitting House members have abandoned their congressional seats to run for the open Senate position, leaving their constituents with a form letter and a promise to 'circle back after the primary.'
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OPINIONI Went to North Side Restaurant Week and Everything Had Foam on It
Tom Hennessey braves the North Side Restaurant Week prix fixe menus and discovers that every dish, beverage, and possibly the napkins have been topped with some kind of artisanal foam.
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OPINIONThe City That Used to Work Now Runs on Oat Milk and Anxiety
Opinion columnist Tom Hennessey takes aim at the modern Chicago lifestyle, wondering when the city traded in its blue-collar grit for overpriced lattes and meditation apps.
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LIFESTYLEI Walked to the Lake Every Morning for 40 Years and Now There's a Scooter in My Way
Tom Hennessey recounts his decades-long morning walk to Lake Michigan and the electric scooter menace that has disrupted the sacred routine.