A one-year deal for Upton makes sense since it would further allow him to build his value in a “make it or break” type of season.
However, a one-year deal for Upton does not make sense for most teams involved since signing the veteran outfielder would result in a team having to part with a draft pick.
Teams that make sense for Upton would be the ones with a protected first-round draft pick. A team in that category is the Chicago White Sox, who have been reported to have interest in Upton.
Signing Upton to a one-year deal would fill a need for the White Sox, given how they have a need for another outfielder. They have shown interest in some of the top remaining free agent outfielders, but are hesitant to go over four-years for one of them, as reported by Bob Nightengale of USA Today.
If the White Sox were to sign Upton, it’s possible a deal could be worth $20 million or somewhere in that range. Losing their second round pick would hurt, but it wouldn’t be the end of the world.
Signing Upton to a one-year deal would put him right back on the free agent market in 2017. The White Sox could then extend Upton the qualifying offer and potentially receive a first- or second-round pick in that years draft.
There are a lot of “ifs” in this column, but adding Upton would be wise of the White Sox on multiple levels.