3 trades Yankees should pursue with Chicago Cubs

The Yankees and Cubs match up too well not to talk trades this offseason.

When the Theo Epstein is away, the Yankees will play.

For years, the baseball world has anticipated an eventual Yanks-Cubs clash in October, with both budding dynasties hitting their playoff peak around the same time.

Unfortunately, the rivalry that was foretold in 2017 has not come to pass, and the cash-strapped Cubbies are in the process of dismantling everything, with their roster-building wizard Theo Epstein foregoing the final year of his contract.

Does that mean it’s time to pounce? The Yankees match up well with Chicago, both in terms of roster needs and literal trade targets, currently floating in the rumor mill. After what feels like an eternity of these two teams being thrown into rumors together (it’s been a while since the Aroldis Chapman-Gleyber Torres trade, after all), let’s try to sort things out and figure out a few deals that make sense for both sides.

3. Kyle Schwarber to the Yankees

The world has been sending Kyle Schwarber to the Yankees forever, so we’ll help them out and drag this to the finish line.

Kyle Schwarber is by far the most likely Chicago Cub to end up elsewhere in 2021, and at this point, we’ve seen him connected to the Yankees too many times to count. Even though Schwarber profiles as the most prototypical DH to ever hit in a designated fashion, and even though the Yankees have Giancarlo Stanton clogging that position for the foreseeable future, the world is still manifesting the fit.

I guess, at some point, where there’s smoke, there’s a square peg of fire attempting to fit into a round hole.

Schwarber’s power bat would certainly play well with the short porch at Yankee Stadium. Famously, as a Cub youngster in 2015, he drove a ball out to right field at Wrigley that landed on top of the mega-scoreboard and laid there, encased under plastic, for the remainder of the team’s playoff run. He’s a powerful pop, high-OBP slugger, and if the Yanks could figure out a rotation for the 27-year-old (part-time LF, part-time DH, part-time 1B?), he’d help with their patience and slugging.

Remarkably, this is Schwarber’s final year before hitting free agency in the 2021-22 offseason, and he could likely be had for a semi-song. Perhaps top pitching prospects Luis Gil (No. 5, per MLB Pipeline) and Miguel Yajure (No. 15) would be enough? That’s plenty of controllable pitching in return for a bat-first slugger who’s about to be lost for nothing.

Not sure we get it either, but the world is crying out for Schwarber in the good color of pinstripes, and we have to give the world what it wants.

2. Javier Baez to the Yankees

Javier Baez could be a flashy just-before-free-agency fit for the Yankees at shortstop.

Yeah, we’re taking stars and giving back prospects across the board. It’s what we do here. Don’t question it.

Remember when the Yankees made Gleyber Torres their official shortstop of the future prior to the 2020 season, instead of simply using him at shortstop without the official designation? 60 games later, the questions about his long-term fit at the extremely important position are reverberating loudly.

With just one year left before he hits free agency among a cloud of star shortstops, Javier Baez’s future is uncertain in Chicago (join the club!). While more likely to be extended than Kris Bryant (LOL), Baez is also coming off a poor 60-game sample that may have clouded his future value. But the 28-year-old free-swinger is an elite defender and arguably the best power-hitting shortstop in the game.

An extension will likely be attached to Baez no matter which team deals for him, and such a move would result in the Yankees disavowing DJ LeMahieu in order to permanently roll forward with a middle infield of their new acquisition in the hole and Torres at the position he held down through 2019. Though there’s only one year of control here, Baez’s current contract would exist in name only — rest assured, there’d be a handshake involved here that would pump up his trade value immensely.

This is an instance where either Deivi Garcia or Clarke Schmidt would lead the package, followed likely by a bonafide big-league bat in Miguel Andujar. Throw in Gil and outfield prospect Canaan Smith (No. 21, per MLB Pipeline), and you just might have a deal here.