The Five Worst Contracts

Many things have been written about terrible contracts, but none this poorly. Let’s cut to the chase, here are the five worst contracts in MLB history, according to me.

5. Carl Crawford – 7 Years, $142 M

Why Horrible: Here’s a really nice breakdown the Business Insider did of why it’s so bad. Here’s another reason. He had 87 at bats this season. That’s $241,379 per at bat. Christ almighty, just give me one of his at bats. And I can’t do that much worse, he hit a dicks-out .185 for the season.  I could accidentally hit .185 with my dick out.  He had 1 (one) triple worth $21 million.  If you look at doubles, he had two, worth about $11 million a pop. They paid him $2 million for every strikeout (11). No matter how you slice it, it’s a dog shit taco.

4. Kevin Brown – 7 Years, $105 M

Why Horrible: So here’s the deal with Kevin Brown – he was actually pretty good for the Dodgers.  He has arguably a Hall of Fame career. If you look at the value they got from him, most breakdowns I’ve seen estimate the Dodgers lost somewhere between $10-$15 M on the deal, which in the grand scheme isn’t so bad.

I think it was a shitty deal because at the time, they clearly needed more help, and they would have been better off spending less money for good young talent that ultimately would have paid better dividends. Plus, I just think it’s a tough pill to swallow when the highest paid player only plays one out of five days. Was it as bad as Mike Hampton? Probably not from a pure value standpoint, but I think during the time frame it was a bad deal.

3. Alex Rodriguez – 10 Years, $275 M; paid roughly $317 M

Why Horrible: $904,184.76. That’s what the Yankees paid him per home run. Was he one of the best players on the field? Yes. Did he crap the crib during the playoffs? You know it. Did he miss time and tarnish the game through implications he used steroids or worse? Of course.

I believe Alex was a really good player and maybe one of the first guys to make it tarnished into the Hall. I also think Alex may be one of the smartest baseball players of all time. But I don’t care what menu you order dong soup off of, it isn’t worth 9/10ths of a million dollars. #overpaid.

2. Ryan Howard – 5 Years, $125 M extension with two years left

Why Horrible: This was a really bad idea from the beginning. Then it got worse. I think Howard is a nice guy, but he for sure won this deal.


1. Jason Heyward – 8 Years, $184 M

Why Horrible: This is year one of  eight. He had an okay season as far as outfielders go. Played in just over 140 games, had 120+ hits. But at the $23 M a year average price tag, that’s almost $500 K for each RBI he drove in. Plus, this post season he’s only played in four games. That’s star powered money to be paying a bench player. I know it’s early in the deal, but this has the potential to be awful. When the smoke clears, the Cubs will regret paying an average outfielder star money.

A few honorable mentions go to Mo Vaughn, Jason Bay, Prince Fielder, Alex Gordon, Carl Crawford again and Pablo Sandoval. At least Pablo can afford new belts with his epic deal.


4 thoughts on “The Five Worst Contracts

    1. For real though, I feel like he was miscoached a little and not everything was his fault. I mean, try harder of course. But sometimes you catch a shitty run of coaches. Look at Alex Smith for the Chiefs.


  1. You said it so I didn’t have to. When you make that much money you have to at least try hard. If that doesn’t work the answer is to try harder. He didn’t do that.
    By the way, 3am is too late ro be commenting on my comments. Go to bed for pete’s sake.

    Liked by 1 person

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