Joe Nathan certainly belongs on the list for a number of reasons. Nathan had put together a really nice career and was coming off two excellent seasons for the Rangers when the Tigers signed him to a two year, $20 million before the 2014 season which was a lot of money for a reliever back then. Most Tigers fans thought the days of getting Jones-ed or Valverde-d were finally coming to an end. Sadly, that was not the case.
Nathan did put up 35 saves in 2014, but his ERA jumped to 4.81 and the inconsistency he showed gave Tigers fans a strong sense of deja vu. Worse than that, though, was that Nathan did not respond well to fans' frustration with his play as he made a decidedly rude gesture to fans during a game in August 2014 that he ended up having to apologize for. 2015 was no better as he made one appearance before hurting his elbow and having to undergo Tommy John surgery which cost him the rest of the season.
This was pretty much a peak "he made a lot of money and didn't play well" problem when it comes to Jordan Zimmermann. Zimmermann was actually one of the jewels of that offseason where the Tigers inked him to a five year, $110 deal as he had been very consistently good with the Nationals up until that point. Unfortunately, the laws of physics and the human body often don't get along that well.
In 99 appearances with the Tigers from 2016-2020, Zimmermann posted a 5.63 ERA which isn't exactly what you want from a guy the team is giving nine figures. There were multiple injured list stints along the way that hampered Zimmermann and his stuff declined significantly from his time in Washington. While never a guy that struck out a million batters, the soft contact he used to be good at getting turned into hard contact and those routine fly balls started turning into home runs. All in all, it was a bad time for all those involved and Tigers fans certainly don't remember him (or his contract) fondly.