Cubs are setting up for a potentially massive winter

Willson Contreras will get the Cubs a huge haul in return

Several contenders could use a proven star behind the dish and at the plate like Willson Contreras. The Mets, Yankees, Red Sox, Astros, and Giants are all potential partners for a trade and they have the prospects to make it interesting.

Let’s say hypothetically, the Cubs trade Contreras to the Mets for a package that features Brett Baty and another prospect or two. Francisco Alvarez is probably far too valuable of a prospect to get for a half-season rental of Contreras but he would be a remarkable addition at the deadline as well.

This deal would allow the Cubs to get a better look at P.J. Higgins behind the plate. Unfortunately, Miguel Amaya has not risen at the rate they believed he could a few years ago and he is just now returning from Tommy John surgery in the Arizona League.

Baty, the 20th-ranked prospect on MLB.com, would be the top prospect in the Cubs’ organization upon arrival. He would also join a list of infield prospects that includes James Triantos, Christian Hernandez and Reginald Preciado.

The Cubs have recently improved the farm system and could do some serious damage with that group if they want to try to improve the Major League roster immediately. Baty could be part of the rebuild or he could help facilitate another trade in the future.

Even if Baty is not involved in a future trade, his presence in the organization could allow the Cubs to move on from other prospects.

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.