Home MLB The 5 WORST Signings In MLB HISTORY!

The 5 WORST Signings In MLB HISTORY!

The 5 WORST Signings In MLB HISTORY!

It’s no secret that sports contracts, especially baseball contracts can blow up in your face.

Unlike football, baseball contracts are fully guaranteed and the value of contracts keeps going up and up and up each and every year.

That’s great for the players – but for teams, if they’re not careful (and smart), they can find themselves on the hook for some pretty ridiculous money.

There is no salary cap in baseball, so every team should spend.

But there’s a difference between spending smartly and spending recklessly – especially on players with red flags.

Whether it’s bad luck with injuries, massive underperformance or just dishing out stupid years and dollars – here are the five worst contracts in baseball history…

#5. Albert Pujols – 10 Years, $240 Million (Angels, 2011)

Some debate whether he was clean or not – but no one can debate Pujols was a great player on the field and a respected leader in the clubhouse.

This wasn’t even about the quarter billion dollars – it was ALL about the years. 

Giving out a TEN YEAR contract to a 32 year old player on the wrong side of his prime with injury concerns???


#4. Carl Crawford – 7 Years, $142 Million (Red Sox, 2010)

This was a horrible fit in every single way.

Everyone knew it, except Red Sox general manager Theo Epstein.

There was a feeling Crawford never wanted to play in Boston in the first place – as the rumor was he hated cold weather.

Injuries and underperformance plagued his short-lived tenure – but adding salt to the wound was the disgust the fan base had for Crawford… He never fit in.

Money down the toilet.

#3. Jacoby Ellsbury – 7 Years, $153 Million (Yankees, 2013)

On paper, this signing made a lot of sense at the time for the Yankees – Purging a five-tool MVP candidate from the rival Red Sox.

But general manager Brian Cashman doesn’t get graded “on paper” – and sure enough, Ellsbury tenure in the Bronx was nothing short of a nightmare.

Simply put, Ellsbury was ALWAYS hurt and could never, ever, ever get on the field.

And the very few times we actually did see him, he resembled absolutely nothing of the player he once was in Boston.

#2. Pablo Sandoval – 5 Years, $95 Million (Red Sox, 2014)

Total disaster.

Yes, the “Kung Fu Panda” was as beloved in San Francisico as he was clutch.

But he was flat-out uninterested in respecting the game or his teammates in Boston.

Look no further than the fact that he never once could be bothered to get into even halfway-decent shape.

His defense suffered. His bat suffered. He was a non-competitive player.

#1. Josh Hamilton – 5 Years, $125 Million (Angels, 2012)

The Angels signing of Josh Hamilton takes the cake.

Hamilton is a great story, but unfortunately a tragic one as well.

He won the MVP with the Texas Rangers and put on one of the greatest Home Run Derby displays we’ve ever seen.

But it was well known that he had his demons.

Unfortunately those demons got the best of him during his time with the Angels.

When he was on the field, his performance lagged tremendously – marred by disappointment and deep slumps.

When it was all said and done, owner Arte Moreno traded Hamilton back to Texas, swallowing a lot of money in the process – with absolutely nothing to show for it.



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