10 Worst Contracts In Chicago Sports History

With news on Sunday night that the Cubs were designating Edwin Jackson for assignment, I immediately jumped into a Twitter conversation with a bunch of folks about what the worst contracts in Chicago sports history have been.

Sadly, Chicago has a pretty tremendous track record of throwing away money on mediocre/over rated/old players, so the hardest part of putting together a top ten wasn’t coming up with ten but cutting the list down.

Here are a few that just missed the cut:

Carlos Boozer – Bulls
5 years, $80M

Orlando Pace – Bears
3 years, $15M

Brian Griese – Bears
5 years, $20M

John Danks – White Sox
5 years, $65M

Bryan Bickell – Blackhawks
4 years, $16M


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  • So Edwin didn't even make the list? Come on, he's worse than Brandon Manumaleuna and even Fukudome.

  • In reply to Jimmy Greenfield:

    Manumaleuna received roughly $300k PER RECEPTION. Edwin is part of my honorable mention list; see him as similar to John Danks but the Cubs, unlike the White Sox, are at least smart enough to cut their losses and move on at this point.

  • In reply to Tab Bamford:

    Edwin is going to end up with $3 million per win! 16-34 with a 5.37 ERA! That has to be top 5 worst.

  • In reply to Jimmy Greenfield:

    but wins are over rated, Jimmy. I kid...

    when the Cubs signed Jackson, they needed an arm and expectations were that he'd suck from most realistic fans. The difference for me w/ others is that the Bears had 2 good TEs on the roster when they signed Manumaleuna, the Cubs didn't need an OF w/ Bradley and hope was irrationally thru the roof w/ Hundley & Fukudome. In my eyes, Jackson was somewhere in between Danks & Huet...

  • In reply to Tab Bamford:

    They didn't actually need an arm with Jackson, it was a foregone conclusion the Cubs would be awful in 2013 and 2014. There was no reason to pay him that money, and you can even argue if he was better it would have been worse for the Cubs. I still have no idea why they felt the need to fork over $48 million in this case. Just an unbelievable waste of money.

  • In reply to Jimmy Greenfield:

    no denying it's an all-time dump of a deal... will be interesting to see if/when/where he ends up next

  • In reply to Tab Bamford:

    He's healthy and, now, cheap. He'll go to a contender trying to capture lightning in a bottle. Bet he goes to play for a manager he previously had success with.

  • In reply to Jimmy Greenfield:

    Sveum in KC?

  • Big Ben: Not to mention that he took it on himself to f--- with Joakim Noah.
    Manymany: At least most football money isn't guaranteed. I'm somewhat surprised that with all his vested money, Cutler's current contract isn't on the list.

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