5) Justin Upton
5-years, $106 million
We start with a verdict that isn’t complete. After acquiring Justin Upton in a late season trade in 2017, the Angels signed the veteran outfielder to a five-year, $106 million contract a few months later. The four-time All Star still has three years remaining on his deal, so it’s possible he could remove his name off lists like this one in the future, but the early results are not promising.
Before signing a new contract with the Angels, Upton was considering opting out of his existing pact that had four years, $88.5 million remaining on it. Instead, he negotiated new terms with the Halos which also earned him a full no-trade clause.
The four-time All Star played mostly as expected during the first year of his deal in 2018, suiting up for 145 games and hitting 30 home runs. But a knee injury slowed him down considerably the following season in which he played in only 63 games and batted a career-worst .215 with only 12 long balls.
Upton will need to bounce back in a big way to justify the hefty price tag on his contract.