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.