Cubs are setting up for a potentially massive winter

Cubs: Acquiring Juan Soto would signal an immediate shift in spending

In order the grab Soto, the Cubs will have to come to terms with a long-term deal that locks him in for over a decade. It will also cost the Cubs a large sum of money to make Soto happy but they have already given that sort of cash to Jason Heyward so there’s no real reason to assume they wouldn’t do it again.

From there, the Cubs can go back and grab Willson Contreras to make things right. He returns on a long-term deal to finish his career with the Cubs while giving them insurance behind the plate and as a DH.

The last major question for the Cubs will be their starting rotation. Marcus Stroman seems like a lock to be in the mix, as well as Justin Steele and Keegan Thompson. However, Chicago needs a true ace in free agency – or via trade – that can take that unit over the top.

If they can land one of the top pitchers available in the winter, the Cubs will be in a good spot. Going after Soto would lend the idea that the Cubs are ready to spend and win, so I would doubt that they get complacent after that move.

The Cubs can play their cards right and be right back in the mix to compete in 2023 with a strong offseason plan. It all starts with the right decision regarding Willson Contreras at the trade deadline, a scenario that is very plausible given his recent comments.