Exploring unlikely ways Yankees and White Sox could work out a Tim Anderson trade

CHICAGO - OCTOBER 10: Tim Anderson #7 of the Chicago White Sox looks on during Game Three of the American League Division Series against the Houston Astros on October 10, 2021 at Guaranteed Rate Field in Chicago, Illinois. (Photo by Ron Vesely/Getty Images)
CHICAGO - OCTOBER 10: Tim Anderson #7 of the Chicago White Sox looks on during Game Three of the American League Division Series against the Houston Astros on October 10, 2021 at Guaranteed Rate Field in Chicago, Illinois. (Photo by Ron Vesely/Getty Images) /

The New York Yankees reportedly taking a step back from the star-studded shortstop market really has us exploring every possible scenario that may exist in the entire world. Universe? It’s close. The one thing we know we don’t want is a one-year free-agent stopgap option. They’re all bad, and such a move would be a sign that the franchise isn’t taking 2022 seriously.

That leaves us with some potential trade options. Aside from Elvis Andrus of the Oakland Athletics, it’s unclear who might be available this offseason — both pre- and post-lockout. But we can dream. And you cannot stop us. Keep quote-tweeting this and saying “stupid.” You’re wasting your own time.

That got us thinking about the Chicago White Sox. They just spent big on reliever Kendall Graveman, who will ostensibly set up Liam Hendriks assuming Craig Kimbrel is likely traded after faltering in a non-closer role when he was acquired at last year’s deadline.

That got us thinking again about the White Sox making further upgrades and re-tooling a bit to further boost their World Series aspirations. At the moment, they have no second baseman, so that’ll likely be the top priority this offseason, but what if they consider spending big on a shortstop to really switch things up? Would they shop Tim Anderson, given the value they could get in return? Probably … not, but can we really rule out anything in one of the most uncertain offseasons ever? And with the dunderheaded Tony La Russa at the helm in Chi-Town with a plethora of shortstops available?

Anderson’s still under a team-friendly deal and will make just $9.5 million in 2022, but the White Sox can afford to spend more with just $155 million committed to next season. Originally, we actually thought the Sox might’ve went after Javier Baez or Marcus Semien to play second base, but those upgrades are no longer available.

Do we know they’re not exploring the shortstop market? Can we really discount any big market team from poking in and sniffing around? Trevor Story and Carlos Correa remain there for the taking.


Tim Anderson would be a dream trade target for the Yankees.

Again, we know that this is most likely off the board. We’d give it a 5% chance. But what if the Yankees and White Sox talked a deal for Anderson? What if that deal included Gleyber Torres (and other pieces) going to the White Sox? Put him at second base for the next few years and pair him with Correa/Story? White Sox fans are in love with Anderson, and for good reason. He’s the glue guy — he brings the intensity and energy in ways so many other players cannot.

But he’s not better than any of those aforementioned options. His three best seasons came in 2019, 2020 and 2021, during which he played 295 out of a possible 384 games. He’s yet to provide longevity and top-notch play. Might the White Sox be considering that, coupled with the fact he could start growing dissatisfied with his upcoming team options of just $12.5 million in 2023 and $14 million in 2024 — both of which carry a TOTAL buyout of $1 million? It’s quite possible. He was an All-Star in 2021 and won the batting title in 2019. If he sees this entire contract through, he won’t hit free agency until he’s 32 years old.


Or what if the deal requires the Yankees to amend Anderson’s contract to make his 2023 option of the player variety? That would give him the opportunity to opt in if he had a bad season and get one more try to build his value, or allow him to hit free agency if he stars yet again so he can enter a free agent class as the likely top option at shortstop. We’d still be open to either offer including Torres, but it probably wouldn’t be much more than that if Anderson has the chance to depart after 2022. Maybe they drop the options altogether.

And it’s a win-win for the Yankees. They likely want a one- or two-year option at shortstop — at least, that’s what we’re gathering if they’re going to be out on the market’s best shortstops.

We know. This exercise is exhausting and complicated. But it’s only because the Yankees have chosen this route by seemingly entrusting unproven prospects and passing on generational talents.

Again, we know this probably won’t happen. But it’s an extremely unlikely option potentially worth exploring if the White Sox want to re-tool by upgrading at shortstop with all the money they have at their disposal, and if the Yankees want to find a way to acquire a near-elite shortstop for 1-2 years before going forth with their desired plan.