As the MLB season heads into the dog days of summer, we all sit in anticipation to see what big names will be moved at the deadline.

Will the New York Yankees get their top of the line pitcher? Will the Milwaukee Brewers make another surprising splash like they did in acquiring C.C. Sabathia in 2008?

We will find out soon.

At this point, we can just sit back and hold out hope that our respective teams can keep winning ballgames—pleading that they are in position to make a bold move at the deadline.

On the other hand, it doesn’t always work out as planned—as no one wants to be on the losing end of a bad deal.

We’ve seen many lopsided deals over the last 20 years—although in most cases it takes years to determine the winner.

Here are the 13 Most Lopsided Deals Since 1990.

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