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White Sox sign Andrew Benintendi to five-year deal

The Yankees will need a new left fielder in 2023.

Kansas City Royals v Chicago White Sox Photo by Nuccio DiNuzzo/Getty Images

The Yankees have done a good job this offseason at checking off important items on their to-do list. They brought back Anthony Rizzo to fortify first base, and more importantly, they also convinced MVP Aaron Judge to return as well, thanks to a big nine-year contract. They took steps to improve their already-accomplished pitching staff as well, replacing Jameson Taillon with Carlos Rodón just last night, and to a less-important extent, swapping in old friend Tommy Kahnle for the likes of Aroldis Chapman, Miguel Castro, and Zack Britton in the bullpen.

One obvious void remains, however, and that is out in left field.* The Yankees acquired Andrew Benintendi from the Royals at the trade deadline to make up for what the departed Joey Gallo (who coincidentally also signed with an AL Central team today) wasn’t providing, and after a slow start, Benintendi really began to pick it up in late August as the Yankees snapped out of their midsummer funk. But a painful hit by pitch a couple weeks later effectively ended his season on September 2nd. So New York had to make do with out-of-position rookie Oswaldo Cabrera and over-the-hill Aaron Hicks down the stretch.

*No, I don’t believe that the Yankees are actually going to ditch Josh Donaldson at third, much to my personal chagrin.

Benintendi’s bat was missed during the playoffs along with DJ LeMahieu’s, and the season went down in flames during an ALCS sweep. Benintendi alone wasn’t going to be enough to make up the difference between New York and Houston, but it hurt nonetheless. Thus, there was some serious thought to the Yankees re-signing Benintendi to a new contract, as both sides seemed to like each other and there was a clear fit.

That won’t come to pass though. Instead, Benintendi is reportedly heading to the White Sox on a five-year, $75 million deal:

My initial reaction was “Well, that’s too bad.” I did enjoy Benintendi’s approach at the plate, and his defense was justifiably enough to be a Gold Glove finalist.

But even acknowledging that owners have all the deep pockets in the world and can afford anything ... that is a long contract for a guy coming off a major wrist injury and who I think only qualifies as a solid player at best. Per Jack Curry, the Yankees’ front office seemed to have the same inkling:

I wish him all the luck in the world and am happy that he is taking money from Jerry Reinsdorf’s coffers, but the Yankees can probably find a better way to fill the gap in left field. Maybe it’s someone on the Twins or Diamondbacks, as rumored the other day, or maybe it’s another free agent. It seems highly doubtful that it will be Hicks or Cabrera.

If told that the Yankees would miss out on any of Judge, Rodón, or Rizzo at the expense of Benintendi ... yeah, sorry to Super Benintendo Chalmers, but I’m making that swap. The offseason rumbles on.