Realistically, there's not many scenarios where the Chicago Cubs are going to trade Matt Shaw this offseason. For one, the Cubs seem to still believe in Shaw's ceiling, and two, right now, Shaw is slated to have an important role in the outfield. That doesn't mean a trade won't happen, and it's possible the path to one is with the New York Yankees.
We must rewind back to the trade deadline. There was a one-for-one trade between the Washington Nationals and Boston Red Sox that had the Cubs' attention. The Red Sox swapped a controllable starting pitcher in Connelly Early for a controllable bat in Curtis Mead.