MLB free agency: Ranking the 3 worst contracts of the 2022 offseason

Second-worst contract: Andrew Benintendi, Chicago White Sox

Contract: 5 years, $75 million.

Immediately after the Andrew Benintendi to the White Sox deal was reported, one rival executive texted: “What an insane deal. Feels like a lot.”

That executive was not alone in that feeling. What ultimately won the White Sox the bidding for Benintendi was their willingness to go to five years. Another team involved in the bidding, the New York Yankees, were not willing to go that far and at that annual average value. But the White Sox were in position where they had to spend and felt that Benintendi, a talented outfielder with very good plate discipline, was the right investment — especially after losing Jose Abreu in free agency.