Cubs are setting up for a potentially massive winter

There is an opportunity for the Chicago Cubs to get better in a hurry if they want to be aggressive in the next six-plus months.

Despite not making any trades so far this season, it is evident the Chicago Cubs are on the cusp of another heartbreaking trade deadline. However, if they approach the coming months properly, this could be the last time fans are forced to endure that sort of pain.

Willson Contreras is the biggest trade chip this roster has to offer and there will be plenty of suitors over the next two weeks. Contreras is perhaps the best offensive catcher in baseball and has the defensive talent to be the missing piece on so many contenders.

With the deadline looming, Contreras has made it very clear that he wishes to remain a Cub but would be open to returning to Chicago in the offseason if he does get moved to a contender. That said, the Cubs could position themselves to have an incredible offseason by trading Contreras as a rental and bringing him back in free agency.

Juan Soto would be the main target of any massive trade in which the Cubs would be the buyers. There is a chance Soto is dealt at the deadline this season but it might be easier to deal the 23-year-old star in the winter. If he survives this season, the Cubs should be all over a trade to bring him in.

It will take a massive haul of prospects and potentially even MLB-ready players to land a player of Soto’s caliber. The Cubs have a nice crop of players that could make a deal happen and they would be even better off if they are able to swing a massive deal for Contreras.

This is a multi-step plan for the offseason but let’s take a look at a scenario in which the Cubs enter the 2023 season with Willson Contreras, Juan Soto, and perhaps even more stars on the roster.