MLB Free Agency: Ranking the 10 Most Crucial Contract Mistakes of the Winter

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Why are human beings drawn to failure?  What makes major mishaps so maliciously magnetic?

The effect seems especially pronounced when it comes to professional sports.  Provided that it's not OUR team making that bone-headed move—fans find a sickening joy in delighting over another team's mistakes.

This twisted logic takes us directly to Major League Baseball's annual winter meetings.

The winter meetings are a place of hope—a small refuge that allows even the worst of teams a moment to dream of a playoff run the following season.  Deals made in the winter can change the fortune of a franchise forever.  GMs can become legends. Dynasties can be built.

It's also where some of the next season's (or decade's) worst moves happen.  Franchise-killing moves. Moves that get GMs fired.  Moves that can cause an entire fan base to lose hope.

So naturally, we focus our attention on those.  Yeah, the head banging, chair throwing, fist-through-wall type of moves.

Why?

Because they're more fun.  (Admit it).

10. Jimmy Rollins

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The Philadelphia Phillies re-signed Jimmy Rollins to a three-year, $33 million dollar contract this offseason, which locked up their shortstop through 2014.

For Philadelphia fans, keeping their beloved "J-Roll" might have seemed like the correct move—but in reality that is just a sentimental thought.

You see, the Phillies are now stuck paying an aging shortstop $11 million dollars per year, until he is 36.  That looks bleak when you consider that he is currently batting .255 with just 4 home runs and 19 RBI through 65 games.

And he hasn't even been injured yet.

Compare that with the Cardinals nabbing the resurgent Rafael Furcal for $4 million dollars per year less than Rollins and it's clear that the Phillies did not come out on the correct end of this deal.

9. David DeJesus

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The Cubs signed David DeJesus coming off of his worst statistical season of his career hoping they had found a bargain.

$4.25 million dollars, 63 games and a mere 2 home runs later, the Cubs are still hoping but not finding.  DeJesus currently holds a subpar .260 batting average to go along with diminishing speed, and the Cubs look to be stuck with him until 2013.

Additionally, DeJesus's woeful presence in the lineup is also contributing to the delay of exciting top prospect Anthony Rizzo's big-league promotion.  Ouch.

8. Francisco Rodriguez

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Francisco Rodriguez's days as "K-Rod"are long gone. 

That's why the Brewers' decision to give him an $8 million dollar contract to serve as a setup man seemed a bit questionable.

It looks even more questionable now.  Through 30.1 innings of relief this season, Rodriguez sports a pedestrian 4.12 ERA and an uglier 1.48 WHIP.

Eight million dollars for that kind of production is just not going to cut it.  On the bright side, it was only a one-year deal.

7. Ryan Madson

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Sometimes, despite one's best efforts, unfortunate events take place.

Such is the case of Ryan Madson. 

Signed during the offseason in what seemed to be a promising move, the Reds and Madson agreed to a one-year, $8.5 million dollar deal.

And then a ligament was torn off his elbow.  Tommy John surgery.  Done for season.  Good-bye, $8.5 million dollars.

Paying for closers is always a risky proposition.

6. Jason Marquis

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This offseason, the Minnesota Twins gave starting pitcher Jason Marquis a one-year, $3 million dollar contract. 

Boy, was that a mistake.

In what amounted to about $430,000 per start, Marquis gave the Twins an 8.47 ERA and a disastrous 1.941 WHIP over seven games before he was mercifully released.

Good grief.

5. Heath Bell

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Remember my advice about paying for closers?

Well, the Miami Marlins learned the hard way.

Heath Bell was signed by the Marlins to a three-year, $27 million dollar contract, and he's responded by posting a 5.68 ERA to go along with a 1.82 WHIP through 30 appearances.  He's still the Marlins de facto closer despite blowing four saves and being removed from the role once already, because quite frankly, the Marlins have limited other options. 

But with two years and $18 million dollars still remaining on the 34-year-old's contract, there is not one Marlin fan smiling about this offseason signing.

4. Casey Kotchman

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It's not a good sign when you are in the discussion for the league's LVP—or least valuable player.

What makes it worse is when you were paid $3 million dollars in the offseason and expected to build upon a breakout season from the year prior.

Casey Kotchman would be the player I am referring to, who is sporting a dreadful .221 batting average through 57 games with the Cleveland Indians so far this season.  Despite his defensive prowess, it's safe to say that the Indians are surely regretting this offseason addition.

3. Coco Crisp

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The Oakland Athletics signed Coco Crisp to a two-year, $14 million dollar deal in the offseason—a move that very nearly makes him untradable.

There are just not many suitors for a 32-year-old batting .199, with declining speed.  In fact, he only has five extra-base hits all season—three doubles, one triple and one home run.

At least he still has the best name in the big leagues?

2. Bruce Chen

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My favorite part about this article is that the writer, the Royals GM and the Royals manager sound delighted over the fact that they just signed Bruce Chen to anchor their staff for two years and $9 million dollars.

Uhhhh. 

If by anchor you mean firmly tie down your team and prevent it from winning ball games?  Then yes.

However, I don't think that's the definition the Royals' front office had in mind.

But unfortunately, that's what they have gotten from the 35-year-old left-hander (happy birthday, by the way), who was never really that good in the first place (see career 4.53 ERA).

He's been especially poor this season, posting a 5.05 ERA to go along with a 1.29 WHIP, and things only seem to project negatively from here.

1. Albert Pujols

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The biggest news this offseason was when the Los Angeles Angels signed Albert Pujols to a 10-year, $250 million dollar deal.

And that's not all.

Hidden in the deal is this list of added perks.  He's got four season tickets for the next 10 years, a guaranteed $1 million dollar per year job after he retires from baseball and a hotel suite on all road trips—just to name a few. 

Seriously?  I didn't even know that they made contracts so obnoxiously gluttonous.

And you think his .256 batting average with 10 home runs for the $12 million dollars they are paying him this year looks bad enough?

It gets better.

You see, his contract only gets fatter as the years roll by.  Not happy with 32-year-old Albert for $12 million?

Just wait until you get 38-year-old Albert for $27 million.

And then 41-year-old Albert for $30 million.

Remember those franchise-killing deals I was talking about?  The Angels are just about to experience what one feels like.