January 20, 2016 – Detroit Tigers sign Justin Upton
Seasons with the Detroit Tigers: 2
Career WAR with the Detroit Tigers: 7.1
The surprise signing of Justin Upton in 2016 mirrored the events of the #2 move on this list in many ways. Detroit’s newly minted GM Al Avila had already made a splash that offseason, trading for Francisco Rodriguez and Justin Wilson, signing Jordan Zimmermann to a huge free-agent contract, and inking multi-year deals with Mike Pelfrey and Mark Lowe. The team still had a hole in the outfield, with one of the corners set to be handled by a combination of Mike Aviles, Tyler Collins, and Steven Moya, but most fans assumed Avila was done.
Then Mike Ilitch decided the outfield wasn’t good enough, and the Detroit Tigers signed Justin Upton to a massive, 6-year, $133 million contract. The early returns weren’t very promising. Upton, the #1 overall pick in 2005, began 2016 in a horrible slump, and by the All-Star break he was a negative WAR player hitting just .235 with 9 home runs and a brutal 31.5% strikeout rate.
He turned things on in the second half, however, and he was the hottest hitter on the planet down the stretch, batting .292 with 13 home runs in September and October to almost single-handedly keep the Tigers in the playoff race. Upton was very good in 2017, making the All-Star team and batting .279/.362/.542 over 125 games, but the Tigers decided it was time to rebuild, and they offloaded Upton’s salary before he could have a more lasting impact on the franchise.