Harper, Machado, and more: Reassessing the 2018-19 MLB free agents

Sep 22, 2021; Philadelphia, Pennsylvania, USA; Philadelphia Phillies right fielder Bryce Harper (3) waits in the outfield before the third inning against the Baltimore Orioles at Citizens Bank Park. Mandatory Credit: Bill Streicher-USA TODAY Sports
Sep 22, 2021; Philadelphia, Pennsylvania, USA; Philadelphia Phillies right fielder Bryce Harper (3) waits in the outfield before the third inning against the Baltimore Orioles at Citizens Bank Park. Mandatory Credit: Bill Streicher-USA TODAY Sports /
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Sep 26, 2021; Detroit, Michigan, USA; Detroit Tigers designated hitter Miguel Cabrera (24) hits during the first inning against the Kansas City Royals at Comerica Park. Mandatory Credit: Tim Fuller-USA TODAY Sports
Sep 26, 2021; Detroit, Michigan, USA; Detroit Tigers designated hitter Miguel Cabrera (24) hits during the first inning against the Kansas City Royals at Comerica Park. Mandatory Credit: Tim Fuller-USA TODAY Sports /

Given the MLB lockout, it may not seem like it, but we’re dead in the middle of the winter free agent signing season.

It is a time of year filled with faith and hope, not to mention plenty of money. Already this offseason, teams have committed $1.7 billion to the signing of available free agent talent in the hope that talent will produce a contender.

But it is also a season filled with peril. Despite the best intentions of players and team execs alike, history tells us that not all free agent signings will look as rosy one or two years from now as they did at the time the deals were agreed to.

Sometimes injuries interfere. In other cases, the problem is that reality comes up short of expectations. The player simply turns out not to be as good as he or the team expected.

On a few occasions, too, the player’s performance justifies the investment, but the weight of the contract hamstrings his team to the degree that it cannot surround him with talent.

There is no better illustration of this potential problem than the Detroit Tigers’ signing of Miguel Cabrera to an eight-year, $248 million free agent deal prior to the 2014 season. Cabrera, who was 33 when the deal took effect, has delivered a series of credible seasons for a player in his age category, averaging .256 with 94 home runs and 359 RBI.

But that contract, which works out to about $30 million per season, has hamstrung the maneuvering to the small-market Tigers. Last year, Cabrera’s deal ate up fully 37.5 percent of the team’s entire player payroll.

And no, the Tigers aren’t cheap. Last year, they committed about 57 percent of revenues to player payroll, probably the highest percentage of any major league team.

To judge how frequently free agent deals work out, all we need to do is hop back to the winter of 2018-19. It was a turbulent free agent signing period, consumed by negotiations over some of the game’s biggest stars.

Here’s an assessment of the 10 most costly free agent deals signed that winter and how those deals worked out.