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5. Justin Upton: Five Years, $106 million, 2017
The Angels traded for Justin Upton from the Tigers in the second year of his big contract with the Tigers. Upton had an opt-out after the season and used it as he was an all-star. Upton ended up signing a five-year $106 million dollar deal to remain an Angel. It started out fine, but ended poorly.
Upton hit 30 home runs in his first year of this new deal and had a 121 OPS+. He played in 145 games that season. He'd play in just 194 total over the next three seasons.
In those three seasons, Upton would slash .211/.299/.414 with 38 home runs and 103 RBI. He had a 90 OPS+. He struggled to stay on the field and when he played he was a shell of his former all-star self.
Upton ended up getting released prior to the 2022 season. The Angels got one good season out of Upton, and then he just disappeared. They wasted four years of big money on this contract.