Law: White Sox pick curious target for largest deal in franchise history

I wrote in my free-agent rankings that I thought Andrew Benintendi would get the largest contract ever for a player who didn’t hit 10 homers or steal 10 bases in his walk year. I didn’t think it would be (*waves hands around frantically*) this large. The White Sox just gave Benintendi five years and $75 million off that platform season, and while there could still be some more offense here for a new team to unlock, this contract all but assumes Chicago is going to find it.

Benintendi’s 2022 season was a bounce-back of sorts but comes with all sorts of caveats. It was his best offensive season since 2018 and only the second time in his career that he was clearly above average as a hitter. He did it without power, drawing more walks and hitting the ball the other way, often sacrificing the potential for extra bases in favor of soft contact, even on pitches he should be able to drive. He’s an average defender in left who could probably stand in center but would be a few runs below average if he played there regularly.

He was a 3-WAR player in 2022, which would more than justify the contract, but a five-year commitment assumes he’s going to hold all or most of that value for at least the next four years, and I’m not sure I see that. Benintendi’s performance in 2022 was driven in large part by a spike in his BABIP while with Kansas City, where he had a .366 BABIP, and that dropped to .303 (.324 career, including 2022) after he was traded to New York. He did show a little more doubles power after the trade, so that mitigated some of his offensive drop, but the batted-ball data doesn’t point to that continuing.

This is a bet that the White Sox can figure something out that his last two employers, at least, could not: getting him to drive pitches in the zone that he currently hits softly, often just the other way. That’s easier said than done, but it’s essential to make this contract work for Chicago. The worst-case scenario is he’s a .305 BABIP guy who makes a ton of weak contact and posts a 104 wRC+ because he walks a lot, and he plays solid defense in left, and he’s worth 1.8 WAR and the deal is neither a win nor a disaster. I don’t think Benintendi is going to be a zero before maybe the last year of the contract, but he’s more likely to be reliably mediocre and thus might 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 their downside risk while still giving them a chance to capture any upside if they do help him improve his contact quality. Five years increases their downside risk enough that it feels like too much.

The White Sox have essentially swapped Benintendi into José Abreu’s spot, although the exchange also moves Andrew Vaughn from left field, where he made Ryan Klesko look like a Gold Glover, to first base. That probably still leaves the White Sox marginally worse off, even if we assume Abreu and Benintendi repeat what they did last year or, as I believe, taper off some in 2023.

They will see improvement from a full season of Eloy Jiménez and should get more from Lucas Giolito in 2023, but that’s not enough to make this team a potential wild-card contender. It still has a huge void at second base and could use an upgrade at designated hitter, or at least a platoon mate for Gavin Sheets, and the free-agent market doesn’t offer any of those. I’m not sure where they go from here if they want to return to the playoffs next season, although I might be short-changing the substantial improvement they made with the change of managers.

Chris Bassitt (Darren Yamashita/USA Today)

• The Blue Jays needed some length to their rotation, someone to provide just league-average innings, or even a touch below league average, with Hyun-Jin Ryu coming off a six-start season and Yusei Kikuchi and José Berrios coming off 5+ ERAs. Chris Bassitt fits that bill; he’s a pretty efficient starter who should eat innings as long as he stays healthy, sinking the ball for quick outs and generally keeping the walks down. He has pitched enough to qualify for the ERA title only twice, including 2022, although he would have done so in 2021 had he not been hit in the face by a comebacker.

I’d like him more if he had just a little better command and control, given his lack of a real out pitch, but I like the fit for Bassitt in Toronto, although the AAV of $21 million (three years, $63 million, you do the math) likely values ​​him as a more durable pitcher than he’s been. It’s good to see someone with this kind of career — only becoming a bona fide big-league starter at age 30, then coming back from a potentially life-threatening injury in 2021 — get paid like this, though.

(Top photo: Denny Medley / USA Today)


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