I wrote in my free agent rankings that I thought Andrew Benintendi would get the biggest contract ever for a player who didn’t hit 10 batters or steal 10 bases in the year of his walk. I didn’t think it would be (waving hands around frantically) this big. The White Sox just gave Benintendi five years and $75 million worth of podium season this season, and while I think there’s still more humiliation here for a new team to open, this contract assumes Chicago will find him.
The 2022 Nintendo Switch was a throwback, of sorts, but it comes with all kinds of caveats. It was his best offensive season since 2018, and for only the second time in his career he was clearly above average as a hitter. He did it without power, pulling more walks and hitting the ball the other way, often sacrificing the possibility of extra bases in favor of soft contact, even on pitches he should be able to drive. He is a medium defender on the left flank and can probably stand in the middle but would be a few times below average if he played there regularly.
He was a 3 WAR player in 2022, which would justify the contract, but a five-year commitment assumes he’ll keep all or most of that value for at least the next four years, and I’m not sure I’m looking at that. Benintendi’s performance in 2022 was largely driven by a huge BABIP spike while with Kansas City, where he had a . 366 BABIP, returning to his career standard of .303 (.307 career, incl. 2022) after he was traded to New York. He showed a bit more power double after the trade, so that mitigated some of his offensive touchdowns, but the hitball data doesn’t suggest that continues.
That’s a bet that the White Sox can figure out something here that his last two employers couldn’t — get him to drive pitches in the area he’s currently hitting softly, and often the other way around. This is easier said than done, but I believe it is imperative to make this contract work for Chicago. Worst case scenario here is he’s a .305 BABIP guy who has a lot of weak contact and posts 104 wRC+ because he walks a lot, plays strong left defense and deserves 1.8 WAR and the deal is neither a win nor a disaster. In fact, I don’t think Benintendi will be zero before perhaps the final year of the decade, but he’s more likely to be reliably mediocre, and so may leave the White Sox unwilling to move on from him when replacing him is the better option. Three years and the same AAV would have limited the downside risk while still giving them a chance to pick up any upside if they helped him improve the quality of his call. Five years increases the downside risk enough that it feels like too much.
The White Sox essentially traded Benintendi for José Abreu, although the exchange also moved Andrew Vaughn from left field, making Ryan Klesko look like a Gold Glover, to first base. That probably still leaves the White Sox in a marginally worse position, even assuming Abreu and Benintendi repeat what they did last year or, I think, both wane in 2023.
They will see improvement from a full season of Eloy Jiménez, and should get more Lucas Giolito in 2023, but it’s not enough to make this team a potential contender. They still have a huge void at second base and could use an upgrade at the designated hitter, or at least a platoon mate for Gavin Sheets, and the free agent market offers none of those. I’m not sure where they’ll go from here if they want to get back into the playoffs in 2023, though I may be short on changing the huge improvement they’ve made with the change of managers.

Chris Bassett (Darren Yamashita / USA Today)
• The Blue Jays needed some length in their rotation, someone to pitch only mid-league innings, or even a touch below league average, with Hyun-Jin Ryu hitting a season with 6 starts and both Yusei Kikuchi and José Berrios striking out 5 + ages. Chris Bassett fits into this law, as he is a very effective player who should eat innings as long as he stays healthy, sink the ball to get out fast and generally keep a walk. He pitched just enough to qualify for the ERA title twice, including 2022, though he would have done so in 2021 had he not been hit in the face by a forward.
I’d like him more if he had a little better command and control, given his lack of real ballpark, but I’d love him to be a good fit for Bassett in Toronto, though I think AAV’s $21m (3yr, $63m, do the math) values him It is a much more durable jug than it was. It’s nice to see someone who had Bassett’s career, only become a true starter in the league when he was 30, and then come back from a potentially life-threatening injury in 2021, get paid like that.
(Top photo: Denny Medley/USA Today)
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