MLB free agency: The future faces of regret

BOSTON - AUGUST 19: The Boston Red Sox introduced Dave Dombrowski as their new President of Baseball Operations during a press conference held in the State Street Pavilion at Fenway Park. Pictured are, left to right, John Henry, Tom Werner, Dombrowski, and Sam Kennedy. (Photo by Jim Davis/The Boston Globe via Getty Images)
BOSTON - AUGUST 19: The Boston Red Sox introduced Dave Dombrowski as their new President of Baseball Operations during a press conference held in the State Street Pavilion at Fenway Park. Pictured are, left to right, John Henry, Tom Werner, Dombrowski, and Sam Kennedy. (Photo by Jim Davis/The Boston Globe via Getty Images) /
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At the beginning of MLB free agency, fans and teams believe that some players deserve a lot of money, but as the season goes on and as the team has to give that player their money, they begin to dislike the decision that was made a year or two ago.

There have been decisions that general managers have come to regret when it comes to MLB free agency.

These noteworthy deals come to mind: the Angels signing Josh Hamilton, Boston signing Pablo Sandoval, Carl Crawford going to the Red Sox, the Mets signing Jason Bay, the Braves getting B.J. Upton for five years, and just last year the Phillies signing Carlos Santana, the Cardinals signing Greg Holland, and of course the Yankees signing Jacoby Ellsbury.

Free agent signings can make or break your team’s plan for years to come because of payroll flexibility, and then other free agents wanting or not wanting to play with that player your team just signed to a mega-contract.

The cornerstone player your team signs will be on banners all around the ballpark, there will be jerseys of him all over the team store, and when your team is not playing well, it falls on him.

It is a difficult job for these superstars to live up to the hype, and a majority of the time they do not live up to the hype, which then falls on the general manager’s shoulders for committing a huge amount of money to that player in the first place.

Every offseason there are players that we will look back at next offseason and know that they got overpaid for various reasons including their individual stats, their leadership, or sadly the team’s record.

Now it’s impossible to know when a free agent signing will backfire on a club, but let’s go through some that I am confident will go wrong.