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.

The Cubs can add enough farm talent to trade for Juan Soto

A package of Baty or Triantos, Caleb Kilian, Kevin Alcantara, and Cristian Hernandez would be a decent starting point for a deal with the Nationals. With how heavily the Cubs attacked pitching in the draft earlier this week, they could even part with more pitching prospects to sweeten the pot.

Aside from Jordan Wicks and DJ Herz, the Cubs should be willing to move almost any pitching prospect in the organization. They have added enough arms to provide depth through the ranks and could look to flip some of them for a bat, which would make the most sense.

Their first two selections from this year’s draft, Cade Horton and Jackson Ferris, will both probably land among the top-15 prospects in the organization once the rankings are updated. That would give Chicago seven pitching prospects at the top of their rankings to go along with Keegan Thompson and Justin Steele already in the big leagues.

Caleb Kilian was the prize of the Kris Bryant trade last summer and could be flipped for another big name if the Cubs get aggressive, which they should. It is time to spend the money and make this club competitive at the highest level.

They could possibly acquire Juan Soto and have a farm system that still features Brennan Davis, Brett Baty, DJ Herz, Cade Horton, Jackson Ferris, Brailyn Marquez, and Jordan Wicks. That would give the Cubs plenty of ammo to either make another splash in the winter or hold off and get a final piece at next year’s deadline.

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.