The great talent and the Chicago White Sox finalized the biggest contract in the team’s history. Yes, the $75 million deal reached was the biggest contract the White Sox have ever given out.

On January 3, 2023, the Chicago White Sox finalized the largest contract in franchise history with… Andrew Benintendi. Yes, the largest contract the White Sox have ever given out was a $75 million agreement with a player who is currently one of the worst in the league, less than a month into his second season with the club.

At the time, $15 million a year for a player like Benintendi may have been a slight overpay, but you could see the thought behind it to an extent. A year and change later, it looks like a huge mistake, as Benintendi’s production has fallen off a cliff in comparison to the peak seasons of his career.

Benintendi was selected seventh overall in the 2015 draft and quickly became one of the top prospects in MLB. He made his debut with the Boston Red Sox at just 21 years old the following year.

After a solid yet unremarkable first full season in 2017, Benintendi was a core piece of the 2018 championship team in Boston and looked to be on track to become one of the top young players in the game.

In 2018, Benintendi slashed .290/.366/.465 while accumulating 4.4 fWAR due to his approach at the plate and strong defense in the outfield. Additionally, he stole 21 bases that season while walking more than 10% of the time and hitting 16 home runs. He was a well-rounded asset with a huge career ahead of him at just 23 years old.

The season that followed was a disappointment for Benintendi. His production fell across the board in 2019, and he finished the year with just 1.2 fWAR and a strikeout rate much higher than the year prior. Still, that was of minimal concern at the time in terms of the scope of his career, given his young age and abundant success over his first two seasons.

However, Benintendi struggled out of the gate in the shortened 2020 season before suffering a season-ending injury. He played in just 14 games that year. Then 26 years old, he was subsequently shipped to the Kansas City Royals in the offseason to begin the next chapter of his career.

Benintendi’s 2021 season was solid, but it was 2022 when he turned in a huge first half, earning the first All-Star selection of his career. He was then traded to the contending Yankees at the deadline. The switch-hitter finished that season with a 122 wRC+ between the two teams, just a notch below his career-best mark in 2018.