Yankees potential trade partner: Chicago Cubs

The Yankees and Cubs have had a fairly rich trade history in recent years, striking several high-profile deals, the effects of which are still very apparent for both rosters. At last season’s deadline, New York acquired Anthony Rizzo in exchange for two prospects. There was, of course, the Aroldis Chapman rental that netted the Yankees Gleyber Torres, and even the deal that sent Starlin Castro to New York had plenty of impact. The Yankees and Cubs are, evidently, not afraid to send some big names to each other, particularly in recent years.

As the 2022 deadline looms on the horizon, another deal between the storied franchises seems well within the realm of possibility. The Yankees are about as legit a contender as there can be, with some holes on the roster that the sell-minded Cubs may be able to fill. The most obvious of these needs are likely at shortstop and in the outfield. And although Jose Trevino has been excellent, there could be improvements at catcher; the same goes for the pitching staff. There are some bigger names that would improve most rosters, as well as some lower-profile acquisitions that could help tighten up parts of this Yankee team.

Cubs catcher Willson Contreras has long been surrounded by trade rumors, and this year is no different, as he will enter free agency this coming offseason. The slugging backstop is in the midst of a career year, posting a 156 wRC+ and slashing a stellar .280/.394/.519. He has ranked as the second-best backstop in the majors at the plate by wRC+, behind only Toronto’s Alejandro Kirk. Contreras would be a huge add to almost any team in the league, and although Trevino has been a pleasant surprise, this would still likely ring true for the Yankees. Contreras would not be cheap as far rentals go, and the Yankees may be content with their Trevino/Higashioka tandem behind the plate, but he is certainly worth keeping an eye on.

Another top-notch target the Bombers could look into on the North Side would be switch hitting outfielder Ian Happ. Similar to his aforementioned teammate, Happ would have a decent price tag, as he too is playing as well as ever. His 131 wRC+ would be a career high, and he is posting career-best walk and strikeout rates, cutting the latter by a significant amount relative to career numbers. Happ also has another year of team control, not entering free agency until the conclusion of the 2023 season. With Aaron Hicks and Joey Gallo showing some inconsistency, or downright poor play, filling that void with a 27 year-old switch-hitting outfielder would be a noticeable upgrade. Whether New York is willing to pay the price it would take will be seen, but Happ is undeniably a tempting player.

They say you can never have enough pitching, and this of course tends to be true. Despite the fact that the Yankees have had the best pitching staff in baseball this season, it never hurts to tighten up whatever loose ends there may be. Chicago’s rotation doesn’t boast many appealing pieces, but there are some intriguing arms in the Cubs’ bullpen.

Mychal Givens and his high-spin fastball are putting up some somewhat pedestrian numbers, in the form of a 3.68/4.42 ERA/FIP. But he has upped his slider use this year and is seeing solid success with it, and could be an intriguing add to a bullpen with some worthwhile pitches. Chris Martin is continuing a solid run as a decent bullpen arm, with a 3.26 FIP this year. And David Robertson is having a bit of a renaissance, posting a 1.86 ERA thus far and a strikeout rate reminiscent of his better days. Regardless, who doesn’t love a good reunion?

The Cubbies have an interesting mix of high-end trade targets, and lower-profile fill-in pieces that could be intriguing to the Yankees. Contreras and Happ would be significant additions for nearly any roster, but also come with a price. New York and Chicago have not shied away from big deals, especially in the recent past, whether that trend continues will become more evident as we approach the deadline.