The rumors are swirling and it seems evident that the Red Sox will break the bank to sign a much-needed bat.

Despite the need, these big contracts have seldom worked out.

1. Manny Ramirez to Boston

In 2000, then Red Sox general manager Dan Duquette, signed free agent Manny Ramirez to an 8 year / 160 million dollar deal. The move, at the time, was a massive deal with epic financial implications.

Ramirez lived up to the contract he signed that winter, hitting a home run in his first appearance at Fenway. He was a key member of two World Series titles in 2004 and in 2007, before being traded in 2008 to the Los Angeles Dodgers.

Manny Ramirez success set the bar for future Red Sox contracts.

Verdict: Win – Manny was everything Boston could have hoped for.

2. Adrian Gonzalez to Boston

In 2010, Theo Epstein signed both Carl Crawford and Adrian Gonzalez to seven-year contracts at 142 million (Crawford) and Gonzalez (154 million).

Adrian Gonzalez had a few solid seasons in Boston before being sent to the Dodgers, along with Crawford.

Verdict: Draw – Gonzalez was solid in Boston, but there were plenty of negatives as well.

3. Carl Crawford to Boston

The Crawford signing was a knee-jerk reaction to his dominance in the AL East. The speedy outfielder emerged as a top-tier threat as a member of the Tampa Bay Rays, before signing with Boston. In Boston, a mix of injuries and inefficiency led to immaculate disappointment.

Carl Crawford will go down as one of the worst free agent signings in Red Sox history.

Verdict: Loss – Crawford never produced in Boston.

4. Pablo Sandoval to Boston

In 2014, Ben Cherington signed both Hanley Ramirez and Pablo Sandoval to free agent contracts for 4 years / 88 million (Hanley) and 5 years / 95 million (Sandoval).

Sandoval, like Crawford, was a giant bust while his weight ballooned and his range and average plummeted. The third baseman was finally released by Boston this past July.

The damage was done; however, as the Red Sox still owe him 42.2 million of the remaining money on his contract, which includes a $5 million buy-out in 2020.

Verdict: Major Loss – What can even be said? He broke the bank AND his own belt in the process…

5. Hanley Ramirez to Boston

The jury is still out on Hanley Ramirez as he has flashed potential, but has not been worth the massive contract.

Verdict: Draw – Hanley’s legacy in Boston still has time to be written.

6. David Price to Boston

Despite the lackluster track record, Dave Dombrowski, was able to sign free agent pitcher David Price in 2016 to a record 7 year / 216 million dollar deal.

The highly paid lefty has not lived up to his contract in Boston. After failing to capture a win in the 2016 playoffs, Price was forced to the bullpen in 2017. Though he had solid success, the Red Sox are not paying him to eat bullpen innings.

Verdict: Loss (For now) – The distraction of David Price results in a loss temporarily. The production hasn’t been terrible, but the issues with the media have been.

Looking Forward

The Red Sox at the beginning of this past season had a total team payroll of $199,805,178, only behind the Yankees and LA Dodgers for highest in baseball.

This is a team that stayed under the luxury tax threshold this past season and by doing so was able to reset the payroll tax penalties that they potentially could accrue if they went over in future years including this upcoming season.

With the past deals, as well as potential issues of exceeding the payroll tax this season, it boggles my  mind that the Red Sox would even entertain trying to trade for Miami Marlins superstar Giancarlo Stanton. The NL MVP finalist is only two seasons into a record-setting 13 year / 325 million dollar deal that he signed in 2015.

The idea of signing a free agent to a monster deal always sounds appealing, but they rarely work out. Dave Dombrowski must keep that in mind moving forward.