The 10 worst decisions in Chicago sports history
If a player, coach or referee makes a mistake, it's easy to move on and forget about it by the next game.
Front office mistakes tend to hurt for decades. The Denver-Miami NBA Finals gives Bulls fans an unpleasant reminder that Jimmy Butler has been to two Finals and Game 7 of the conference finals since being traded by the Bulls in July 2019. The Bulls haven't done any of that since 1998.
At the same time, it's appropriate that Chicago's greatest sports moments were created by other teams' blunders. The Bulls might still be without a title if Portland drafted Michael Jordan instead of Sam Bowie. The Colts took Art Schlichter instead of Jim McMahon. The Blues and Penguins passed on Jonathan Toews in 2006.
With Butler playing Finals Game 2 with the Heat on Sunday, let's take a look at the worst decisions in Chicago sports history. We're talking about moves that ruined good teams, crushed potential championships or both.
1. Cubs trade Lou Brock
The Cubs of the late 60s, early 70s couldn't make the playoffs with four Hall of Famers. Would a fifth have made a difference?
On June 14, 1964, the Cubs fielded a lineup that included Lou Brock, Billy Williams, Ron Santo and Ernie Banks from two through five in the batting order. Brock hit a 2-run homer in a victory over Pittsburgh.
The next day, the Cubs traded Brock to the Cardinals for pitcher Ernie Broglio, which nearly 60 years later is still the Willis Tower of terrible decisions.
Some have said the deal didn't seem so bad at the time, since Broglio had gone 18-8 with a 2.99 ERA in 1963. At the time of the trade, the Cubs were 27-27, 5½ games out of first place and things went south quickly. They lost Broglio's first six starts and were out of contention by July 1. The right-hander went 3-12 with a 6.61 for the Cubs the next two years and was done.
Brock helped the Cardinals win the World Series in '64 and '67, finished second in MVP voting in '74 and collected his 3,000th hit against the Cubs in '79. So good for him.
2. Blackhawks trade Phil Esposito
After having the good sense to sign both Esposito brothers, the Hawks traded Phil to Boston on May 15, 1967. The Blackhawks twice lost the Stanley Cup Finals to Montreal in 1971 and '73, and Phil Esposito was the NHL's leading goal scorer both seasons. They did get Pit Martin in the deal, but it wasn't the same.
There's a story about Esposito being traded because after having a few drinks at a Christmas party, he blurted toward coach Billy Reay and GM Tommy Ivan something along the lines of, "We have a great team here, but you two are going to screw it up." Turns out, Esposito was right.
3. Bears pass on Patrick Mahomes
On the surface, this was a horrendous decision. The Bears wanted a QB and traded several picks in the 2017 draft to unnecessarily move up one spot to take Mitch Trubisky, when they could have had Patrick Mahomes, who's already become an NFL legend.
Realistically, though, Mahomes might have failed in Chicago since Travis Kelce, Tyreek Hill and Andy Reid weren't here waiting for him. The Ryan Pace drafts were a mess.
4. Bulls trade Jimmy Butler
This decision wasn't necessarily about the Bulls thinking they made a great trade. The management team of Gar Forman and John Paxson were feeling some heat after canning coach Tom Thibodeau and wanted to buy time by launching a rebuild. Also, Butler is a challenging personality and the Bulls prefer players that won't complain about the franchise's low desire to build a great team. The Heat doesn't worry about stuff like that.
5. Bulls fail to sign Maurice Lucas
Lucas was the Bulls first-round pick in 1974 out of Marquette and not only would have been a perfect complement for the final year of the Jerry Sloan, Norm Van Lier, Bob Love, Chet Walker lineup, he also handed the Bulls a heartbreaking first-round playoff loss while playing for Portland in '77.
But the Bulls somehow got outbid by the ABA's Spirits of St. Louis, who paid him a reported $120,000. The Bulls didn't sign 1973 first-round pick Kevin Kunnert, either.
6. Blackhawks give away goalie
Yeah, the Hawks made bad trades for Jeremy Roenick and Ed Belfour, but at least the ensuing 10-year slump led to the draft picks that created the three Cup-winning teams. Sending future Hall of Fame goalie Dominik Hasek to Buffalo in August 1992 for a fourth-round pick and Stephane Beauregard happened at point where they could have won something in the 1990s.
7. Cubs can't settle on reliever
Rafael Palmeiro is linked to the steroid era now, but he also hit 569 home runs. The Cubs traded him (and pitcher Jamie Moyer) in 1988 to Texas for reliever Mitch Williams and a few others. Williams helped win a division title in 1989, but was a one-year wonder with the Cubs.
They wouldn't have been in such dire need of a reliever if they didn't trade Lee Smith and Dennis Eckersley a few years prior. Smith was an all-star five times after leaving the Cubs, while Eckersley piled up 390 saves after being traded in '87.
8. Ditka for Concannon
Mike Ditka's best days were over by 1967 and the Bears needed a quarterback, but Jack Concannon wasn't the answer. Neither were Bobby Douglas, Kent Nix, Larry Rakestraw or Gary Huff. Virgil Carter might have been the answer, but the Bears cut him.
This is all just fodder within one of the worst failures in American sports history: The Bears drafting both Gale Sayers and Dick Butkus in 1965, then never making the playoffs.
9. White Sox name Hawk Harrelson GM
His reign was brief (from 1985-1986), but Harrelson is credited with a trio of bad moves -- firing manager Tony LaRussa, firing assistant GM Dave Dombrowski and trading Bobby Bonilla to the Pirates for Jose DeLeon. Dombrowski might have been the worst of the three, since he's led teams to five World Series appearances and won two.
The Sox still went on to a mini-glory era led by Frank Thomas and Robin Ventura. They flipped DeLeon for Lance Johnson, won a division title in 1993, and it's hard to say if LaRussa would have made a difference.
This could also be wrapped into an outside bad decision -- American League owners rejecting Bill Veeck's plan to sell the White Sox to Ed DeBartolo in 1980, forcing Veeck to turn to the Jerry Reinsdorf-Eddie Einhorn group.
10. Gone too soon
Two more terrible baseball trades deserve consideration. The White Sox giving up Fernando Tatis Jr. for James Shields on June 4, 2016 is already a disaster, even if the jury's out on how good Tatis will be.
The Cubs trading two-time batting champ Bill Madlock to San Francisco in 1977 represents the era of when the Cubs had a good player, they'd trade him for two mediocre players to save money. In this case, it was Bobby Murcer and Steve Ontiveros, who had some decent years on the North Side while Madlock won a World Series with a team that could afford to pay him, the Pittsburgh Pirates.