15 worst Detroit Tigers free agent signings in franchise history

The Detroit Tigers have given out a lot of bad money over the past few decades, whether it be in free-agent contracts or extensions that didn’t turn out. Unfortunately over the past 10-12 years, we have quite a few to choose from.

You will see familiar, frustrating free-agent signings like Jordan Zimmermann, Victor Martinez, Mike Pelfrey, and Mark Lowe, to name a few obvious ones. 

Many of them come from the recent past, as Al Avila’s time helming the franchise resulted in more than a few big misses.

There may be a few surprises from a little further back, too, as it’s not as if Dave Domrbrowski were totally perfect himself. And the losing Tigers from the 1990s didn’t often spend much money, but still managed to make a few high-profile whiffs of their own. 

Before we dive in, a big thank you to stories at Bless You Boys, Vintage Detroit, and here at Motor City Bengals for being valuable resources that made researching and thinking about the list so much easier.

Now, let’s re-live some of the worst free-agent contracts in Detroit Tigers history. 

Detroit Tigers Worst Free Agent Signings in Franchise History: Which was Motown's worst deal?

Honorable mention:

HM: Miguel Cabrera, 2016-23

We’re kind of breaking the premise here before we settle into the list of worst free agents, but we’d be remiss if we didn’t mention this as not just one of the worst Tigers contracts of all time but one of the worst in MLB. 

Rewarding a Triple Crown winner, multiyear MVP, and sure-thing future Hall of Famer seemed like a good idea. He was a fan favorite and one of the biggest names in baseball in 2014 when the Tigers announced an eight-year, $248 million deal that would carry him from 2016 to 2023 with a mutual option for 2024 and 2025. Imagine how the fans would have reacted had the Tigers began tearing down the team and letting superstars walk. 

A combination of unaffordable stars leaving, whether through free agency or by trade, and winning World Series titles elsewhere happened anyway. Meanwhile the Tigers were stuck with one of the worst contracts in baseball history.

It started off well. In 2016 Cabrera played in 158 games, was worth 5.1 WAR. He had 38 home runs and .956 OPS (155 OPS+). He never played in that many games again.

Various injuries took a toll, from groin issues to hamstring pain to a torn tendon in his left biceps and beyond. From 2019 to 2022, Cabrera’s OPS dropped to .700 with 94 OPS+ (100 is average). He has been worth at best 0.2 WAR in 2018, per Baseball Reference, and at worst -1 in 2022. He has earned $30 million or more each year. 

There have been highlights – the 3,000th hit, the 500th home run. A fan favorite will retire a Tiger. But overall it’s been an expensive, costly mistake. It’s hard to watch his career end like this.

Now let’s begin our list with some much less costly mistakes and work our way back up.

Other HM

For the same reasons, Gary Sheffield (signed an extension in order to agree to the trade in 2007) and Dontrelle Willis (extension) may otherwise have made the list, but don't technically qualify for this particular list.