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Yankees potential trade partner: Chicago White Sox

The White Sox could be this year’s source of rotation and bullpen help at the deadline if they do indeed sell.

MLB: Los Angeles Angels at Chicago White Sox Kamil Krzaczynski-USA TODAY Sports

Somehow, we’re hardly a month out from the trade deadline, and we’re still trying to get a handle on who the buyers and sellers will be at the trade deadline. Barring a catastrophic next month, the Yankees, of course, will be buying, but the White Sox find themselves in a weird position. Their 34-47 record is the third-worst in the AL — sixth-worst in MLB — but the cesspool that is the AL Central has left them still just six games out of a playoff spot with three months and change to play.

With the division still just one red-hot streak away and a front office whose seats are hotter than they’ve ever been in their nearly 25-year tenure, the Sox will be under tremendous pressure to stand pat or even buy. But if the downward trend of their season continues through July, they have a few players who might be of interest to the Yankees.

A playoff team can never have enough good relievers, and in spite of their disaster of a season, the White Sox have quite the stable of high-octane bullpenners coming in at a variety of contract and career stages, and cost. Even if he wasn’t out at least until mid-July with elbow inflammation, it seems unlikely that Liam Hendriks, a clubhouse leader and perhaps the team’s most popular player among fans, would have been on the move in any case, but at least one (if not both) of the other two high-priced arms in the back of their bullpen are likely to be elsewhere by the end of deadline day.

Kendall Graveman (owed $8 million next season) and Joe Kelly ($4 million buyout of a $9.5 million club option) both have arsenals that would be at home in Matt Blake’s repertoire, each armed with a high-90s four-seamer/sinker combo as well as multiple breaking balls. Neither would come at a very high cost to the Yankees farm system. If Chicago’s primary goal is to free themselves of the payroll hit, any player going back their way probably isn’t going to be among the Yankees’ 20 best prospects.

If Chicago wants a decent prospect back, the name they might offer is Keynan Middleton, who’s rediscovered the velocity on his fastball and has a 2.33 ERA and 33-percent strikeout rate on a league-minimum contract. If they want to aim for more upside, lefty Aaron Bummer (owed $5.5 million next season with $15 million in club options between 2025-26) might also be available for a relative pittance. The lefty with two nasty, outlier pitches — a bowling ball sinker that generates Clay Holmes-esque ground-ball rates and a sweeper with 18 inches of side-to-side break — worked to a 2.59 ERA between 2019 and 2022 but has struggled with control this year, working to a 6.58 ERA this year.

On the rotation side, a Lance Lynn reunion feels quite unlikely, and there have been no whispers of Michael Kopech’s availability, but their staff does boast a pair of interesting possible targets (with different costs) in Lucas Giolito and Dylan Cease. Giolito is a free agent at the season’s end and is not expected to re-sign with the White Sox, while Cease has two more seasons after this one left to play before reaching the open market.

MLB: Boston Red Sox at Chicago White Sox Jamie Sabau-USA TODAY Sports

Chicago hasn’t indicated any willingness to embark on another rebuild so soon. Thus, a deal for Cease is far-fetched unless a team wants to offer a package substantial enough to convince the Sox to forgo two more years of the reigning Cy Young runner-up.

Giolito, however, is a name they may be connected with. He struggled with COVID-19 and a velocity dip to a 4.90 ERA last year after accumulating the seventh-most fWAR of any qualified pitcher between 2019 and 2021, but has once again found his form this season, running a 3.41 ERA (4.20 FIP) nearly perfectly in line with his 19-21 rate. Although the crackdown on sticky substance robbed Giolito of a few strikeouts, he’s compensated with improved command of his slider and bugs bunny changeup this season. However, his fly ball-heavy approach isn’t an ideal fit for Yankee Stadium, and his trade return would likely have to be compelling enough to make the White Sox choose it over whoever they’d get with the compensation pick earned with a rejected qualifying offer, so ultimately, this might not be the greatest fit.

There’s not a whole lot the White Sox can do for the Yankees on the offensive side. Nobody in the infield who would be an clear upgrade over what the Yankees have now (Tim Anderson has had a tough 2023), and if they wanted Andrew Benintendi at five years and $75 million, they would have given it to him as a free agent last offseason. At the height of the dysfunction in Chicago this season, there may have been a world in which a Godfather buy-low offer for Luis Robert Jr. was in the realm of possibility, but the 25-year-old has since rebounded with a monster May and June to nix any thought of that.

MLB: Chicago White Sox at Los Angeles Angels Jayne Kamin-Oncea-USA TODAY Sports

If the White Sox did want to cut bait on an outfielder, and if the Yankees were to be involved in it, Eloy Jiménez presents a intriguing possibility. The 26-year-old is under contract through 2026 and has struggled with consistency in recent years, missing significant time with injury each of the last three seasons and sandwiching a 140 OPS+ in 2022 with a pair of 99s in 2021 and 2023. On the one hand, Jiménez is a lumbering, awkward right-handed hitter with plate discipline issues and poor left field defense. The Yankees already have enough of those, and in many ways, Jiménez would be redundant to Giancarlo Stanton.

On the other hand, Jiménez is also possibly a swing change away from unlocking Stanton-esque power. His contact quality is tremendous, but he’s run ground-ball rates over 50 percent in three of the last four seasons, and whoever can get him to put the ball in the air more will be getting a hitter resembling Edwin Encarnación in his prime. If the Yankees think they know what he needs to do to make that happen, it might be worth losing whatever prospect package it would take to get him here.