CHGO Ranks: The Top 10 ‘What Ifs’ in Chicago sports history

It’s CHGO Rank Week!

We’re counting down the Top 10 “What If” storylines in Chicago sports history. They’re the moments we go to bed dreaming of in an alternate reality — or nightmare — and the plays we wish we could have back.

Lives ruined, friendships lost — think of all the arguments over whether or not the Bears would’ve won the Super Bowl had Cody Parkey’s double-doink deflected through the uprights.

We’ll never really know how things might be different if these alternative histories were real, but it was a fun exercise nonetheless, and I’ve already spent too much time arguing with friends about what made and missed the cut.

“WHAT IF you made your own list, then, huh?”

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10. What if George S. Halas had shown up to the SS Eastland on time?

WHAT HAPPENED: On July 24, 1915, the SS Eastland, headed for a Western Electric company picnic in Michigan City, Indiana, overturned in the Chicago River, killing 844 employees and family members. To this day, it is still the deadliest day in Chicago’s history. George Halas, 20 years old at the time and an employee of Western Electric, arrived at the dock late, missing the ship’s departure and potentially sparing his life.

Over the next five years, Halas graduated from the University of Illinois, served in the Navy, was named the 1919 Rose Bowl MVP, and even played for the New York Yankees for 12 games — all before moving to Decatur for a job with the A.E. Staley Company, where he became a player-coach of the company’s football team. In 1921, he took control of the team, moved it to Chicago and renamed it the Bears.

WHAT IF Halas was on the SS Eastland? Would the Bears exist? The NFL? Sure, football predates Papa Bear, but the league probably wouldn’t look anything like it does today. I can tell you one thing — without the Bears, CHGO Sports wouldn’t exist. So, thanks to George Halas and his tardiness as a 20-year-old.

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9. What if the White Sox hadn’t traded Sammy Sosa?

WHAT HAPPENED: On March 30, 1992, the Sox traded Slammin’ Sammy Sosa and Ken Patterson to the Cubs in exchange for outfielder George Bell. At the time, Sosa had hit just 28 home runs in 302 games over three seasons with the White Sox.

But after being dealt to the Cubs, Sosa smacked 545 dingers over 13 seasons, becoming an NL MVP, a seven-time All-Star, and a six-time Silver Slugger award winner. Sosa changed baseball for good in Wrigleyville, and his popularity forever widened the gap between the Cubs and Sox, despite his alleged use of performance-enhancing drugs.

[WHAT IF THE SOX DIDN’T RE-HIRE TONY LA RUSSA?]

Meanwhile, Bell played out the final two seasons of his career on the South Side, slashing a dismal .227/.276/.382. The former MVP with the Blue Jays ultimately became one of the most disappointing acquisitions in White Sox history.

WHAT IF the Sox didn’t include Sosa in the trade across town and kept the slugger in their outfield for years to come? Would Sosa have abused steroids in the locker room with Frank Thomas present? Sosa might not have become a member of the 600 home run club, but he might have alternatively made the Hall of Fame with a cleaner résumé.

However, without a trade to the Cubs, the Summer of ’98 home run chase loses a bit of its flair with Sosa and Mark McGwire only meeting once in the middle of June. Would baseball look the same without the summer that put the game back on the map?

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8. What if the Blackhawks lost Game 5 in OT to the Predators in 2010?

WHAT HAPPENED: Locked in a 2-2 series tie, the Blackhawks had their backs against the wall late in the third period of Game 5 of the first round against the Nashville Predators. At one point, the Blackhawks led the game on home ice, 3-1. But two Martin Erat goals in the third flipped the script, leaving the Blackhawks down 4-3 in the waning moments of regulation.

All hope seemed lost when Marian Hossa was whistled for boarding with 1:03 left in the third. A five-minute major. A backbreaker. Shorthanded and with the net empty, Patrick Kane tapped home a rebound in an empty crease vacated by Predators netminder Pekka Rinne, forcing overtime.

The Blackhawks miraculously killed the remaining four minutes of Hossa’s major penalty to open the overtime period. As Hossa left the box and the United Center crowd collectively lost its mind, the Blackhawks’ big free-agent acquisition of the previous offseason parked himself to the side of the crease, perfectly positioning himself for another golden rebound to lift the Blackhawks to a 5-4 victory and 3-2 series lead.

With all momentum on their side, the Blackhawks won Game 6 in Nashville, took down the Vancouver Canucks in six games, dispatched the San Jose Sharks in a four-game sweep, and won their first Stanley Cup in 49 years after another six-game series against the Philadelphia Flyers.

WHAT IF the Blackhawks couldn’t kill Hossa’s penalty and the Predators won Game 5? Does the dynasty ever take shape? The Blackhawks likely would’ve lost Game 6 in Nashville without the momentum in their favor. And after another early playoff exit, and with contracts needing to be paid, there’s no guarantee that the team ever recovers well enough to take another swing at a ring.

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7. What if Derrick Rose didn’t tear his ACL in 2012?

CHGO Bulls‘ Will Gottlieb ran an AI simulation to create an alternate history where Derrick Rose never tore his ACL in the 2012 playoffs.

You can find that here!

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6. What if 1998 wasn’t The Last Dance?

WHAT HAPPENED: After six championships in eight years, Jerry Reinsdorf was sick and tired of winning so much. In a feud between players, coaches and management, Reinsdorf sided with general manager Jerry Krause, effectively ending his relationship with head coach Phil Jackson. No Jackson meant no Michael Jordan, either. And without Jordan in the fold, Krause opted to end the dynasty by shipping out Scottie Pippen and Dennis Rodman.

WHAT IF the Bulls decided to run it back in 1999? The lockout-shortened season ended with Steve Kerr, Will Perdue, and the San Antonio Spurs hoisting the Larry O’Brien trophy; could it have been the Bulls instead? The Bulls were aging, but the Eastern Conference didn’t have many hurdles for the greatest player and team of all time.

Without a doubt, the Bulls would’ve represented the East in the Finals in ’99, and Jackson vs. Gregg Popovich would’ve been a terrifically coached series. But I’m okay leaving Mike’s perfect Finals record intact, and in hindsight, going out on top is rarely ever a bad thing.

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5. What if baseball didn’t go on strike in 1994?

WHAT HAPPENED: The White Sox had the best record in the American League. Frank Thomas had cemented himself as a bona fide star, winning the AL MVP award the season before. He was even better in 1994, slashing .353/.487/.729 with 38 home runs in 113 games.

Then, for the first time in 90 years, the World Series was not played. A disagreement between owners and the MLB Players Association on the implementation of a league-wide salary cap led to the season grinding to a halt on August 12, 1994.

WHAT IF the ’94 Sox got their shot? They were built to win that season. And by the time the game came back in ’95, the magic was gone. The core slowly broke apart, and the window didn’t open for another decade. But given the opportunity, it’s hard not to imagine Frank Thomas becoming baseball royalty and making the White Sox the team of the ’90s in Chicago.

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4. What if Alex Gonzalez hadn’t booted it in Game 6?

WHAT HAPPENED: Up in the series, 3-2, with a chance to clinch their first NL pennant since 1945, all the Cubs had to do was not completely self-destruct with a 3-0 lead in the eighth inning of Game Six against the Florida Marlins in the 2003 NLCS.

Manager Dusty Baker opted to keep Mark Prior in the game after the Cubs’ ace had thrown seven shutout innings, allowing just three hits. Prior quickly retired Mike Mordecai before surrendering a double to Juan Pierre and walking Luis Castillo before Ivan Rodriguez drove in Pierre on an RBI single.

Two-run game, one out in the inning and two runners on, Prior got Miguel Cabrera to hit a sharp grounder to short for a double play that would’ve ended the inning, but Alex Gonzalez squeezed his glove a split-second too early, loading the bases for Derrek Lee. Lee doubled, tying the game, and the Marlins scored five more runs in the eighth to win, 8-3.

The Marlins won Game Seven the next night to advance to the World Series, where they won their second Commissioner’s Trophy in franchise history.

WHAT IF Gonzalez had turned the double play to limit the damage to one run? Could the Lovable Losers’ championship drought have ended against the Yankees two weeks later? Would Steve Bartman, who was infamously and wrongfully accused of interfering with a foul ball in Castillo’s at-bat, be a household name among Cubs fans?

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3. What if the Bears had drafted Patrick Mahomes in 2017?

WHAT HAPPENED: Entering the 2017 NFL Draft, the Bears held the No. 3 overall pick after a dismal second season under head coach John Fox. The Cleveland Browns took future Hall of Famer Myles Garrett with the first pick, leaving the San Francisco 49ers on the clock.

Then, Bears general manager Ryan Pace made the move that would ultimately define his legacy in Chicago. Trading the No. 3, No. 67 and No. 111 picks in the ’17 draft, along with the Bears’ 2018 third-round selection, in exchange for the No. 2 pick, Pace selected quarterback Mitchell Trubisky out of the University of North Carolina.

Pace had also signed former Buccaneers QB Mike Glennon when free agency opened a month earlier. Glennon started four games to begin the 2017 regular season before being benched for Trubisky, and Fox was fired after a five-win season.

Trubisky ultimately flopped in Chicago, winning one division title in 2018 before hitting free agency in 2021, failing to earn a second contract with the Bears. Pace then drafted Justin Fields in the 2021 NFL Draft before he was fired to begin the following offseason.

The choice to select Trubisky was immediately ridiculed, with Clemson’s Deshaun Watson and Texas Tech’s Patrick Mahomes still on the board. And to make hindsight worse, Mahomes has since become one of the game’s greatest quarterbacks of all time with the Kansas City Chiefs, winning three Super Bowls in seven seasons as their starter.

WHAT IF the Bears had drafted Mahomes instead? Would Ryan Pace still have his job with the Bears? Would Mahomes have found the same — or similar — success with the Bears? Everything about Mahomes as an NFL superstar tells us he was an incorruptible prospect and would’ve survived John Fox’s developmental strategy. Would the Bears even have needed Cody Parkey’s game-winning attempt in 2018?

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2. What if it hadn’t rained in Game 7 of the 2016 World Series?

WHAT HAPPENED: After coming back in the series from down 3-1 to force Game 7, the Cubs had blown a lead as large as four runs and were stuck in a glass case of emotion. After Cleveland Indians centerfielder Rajai Davis’ game-tying two-run home run in the eighth inning, the Cubs were lifeless.

Then, a storm cell moved into the area, resulting in a 17-minute rain delay. In those 17 minutes, Jason Heyward rallied the troops with an inspiring speech in the visitors’ weight room at Progressive Field.

When the rain passed, the Cubs emerged from the clubhouse with life, seemingly moved on from what had transpired in the eighth. Kyle Schwarber singled, and Anthony Rizzo was intentionally walked before Ben Zobrist smacked an RBI double down the left field line. Miguel Montero tacked on an insurance run with a single — his first hit of the World Series, and first hit since his go-ahead grand slam in Game One of the NLCS.

Carl Edwards Jr. recorded the first two outs of the bottom of the 10th before Mike Montgomery came in for the first save of his career. Then, the Cubs came pouring out of the dugout, jumping up and down like a bunch of delirious ten-year-olds.

WHAT IF the tarp never came out? Would the Cubs have mentally rebounded in time to mount their 10th-inning rally? Would the World Series drought be approaching 118 years? It’s not a foregone conclusion to assume the Cubs would’ve lost, but the delay and moment to process, grieve and breathe absolutely played a significant role in the Cubs winning their first World Series since 1908.

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1. What if Michael Jordan hadn’t retired in 1993?

WHAT HAPPENED: The Bulls had just completed the three-peat, defeating the Atlanta Hawks in six games to win the 1993 NBA Finals. Michael Jordan had cemented himself as the greatest basketball player in the world, and while Jordan was burning himself out, the Bulls were primed to make a run at a fourth consecutive ring in 1994.

Then, on July 23, Jordan’s father was tragically murdered in Lumberton, North Carolina. Three months later, Mike decided to walk away from the game of basketball. Jordan would eventually scratch his athletic itch by turning to baseball with the Chicago White Sox organization, but the Bulls didn’t have their postseason killer, losing in the second round of the playoffs to the New York Knicks.

Jordan came back to the Bulls in 1995, but his late-season return still led to a second-round exit. The Bulls finally reached the mountaintop again in 1996 (and 1997 and 1998).

WHAT IF Jordan hadn’t retired in 1993? Would the Bulls have won as many as eight titles in a row? Almost certainly not. But it would’ve been impossible to bet against Jordan and the Bulls in 1994 and 1995. And as Big Dave pointed out in our CHGO Sports Top 10 “What Ifs” show, we wouldn’t have seen John Starks’s 2-18 choke job in Game 7 of the ’94 Finals against the Houston Rockets.