4 way too early Chicago Cubs offseason predictions

With the trade deadline over and the Chicago Cubs way outside the picture when it comes to thinking about October baseball, it is time to talk about the some way too early offseason predictions.

This offseason’s major free agents include the likes of Aaron Judge, Dansby Swanson, Trea Turner, and Jacob DeGrom, and it would be great if the Cubs could sign one of them. But if that’s now how things play out and ownership waits one more year to spend big money, there are still guys out there who could help this team start to turn the corner.

Furthermore, there are guys on this roster right now whose future is uncertain. Figuring out the best path forward for them will be near the top of Jed Hoyer and Carter Hawkins’ offseason to-do list, as well.

Willson Contreras (C)

Chicago not trading three-time All-Star catcher Willson Contreras ranked as one of the biggest surprises of the deadline, but it also gives me hope the Cubs might work out an extension with him.

As Contreras could arguably be the best offensive catcher in baseball right now, he will not be cheap. His next contract  could be similar to J.T. Realmuto’s 5-year, $115.5 million deal with the Phillies, Buster Posey’s eight-year, $159 million deal with the Giants or Yadier Molina’s three-year, $60 million pact with the Cardinals.

All three of these players lived up to their contract with their respective teams, despite ranking among the league’s best-paid backstops. It would not surprise me if Contreras tries to become the highest paid catcher ever, but with his skillset and leadership, he’s worth every penny in my mind.

Patrick Wisdom (3B)

Patrick Wisdom is an interesting case for the Cubs, as he is currently in pre-arbitration and will not be a free agent until 2027. But Wisdom is 30 years old and, now that the entire league uses a designated hitter, there must be teams who’d love to add him to their lineup in 2023. We have seen how other teams will trade, especially for a pure power hitter. As Wisdom is locked up for years, trading him in the offseason in order to call up one of the younger players may be worth it.

Just look at what the New York Yankees gave up for Joey Gallo. In 2021, Gallo hit 38 homers with 77 RBI, whereas Wisdom hit 28 homers with 61 RBI. Gallo played in 153 games and Wisdom played in 106. Their numbers are incredibly similar. The Yankees gave up their #17, #22, #23, and #27 prospects for Gallo, whom they wound up trading to the Dodgers a year later. Trading Wisdom seems almost necessary with the amount of minor league talent the Cubs have in the infield mix.

Jameson Taillon

With the signing of Marcus Stroman, Hoyer showed that he wants to spend money on pitching, as well as continue to develop it. This year’s starting pitching free agent class is not that strong, with Noah Syndergaard, Tyler Anderson, Mike Clevinger, Sean Manaea and Jameson Taillon being the top arms available.

Even though Taillon’s numbers are not too flashy, he is consistent. During Taillon’s first four seasons with the Pittsburgh Pirates, he worked to a 3.67 ERA. Then Taillon was traded to the Yankees and, in two seasons, he carries a 4.14 mark. Even though that isn’t as low as I’m sure he or New York would like it to be, he has proven himself to be consistent.

So far this season, the Cubs starter with the most innings pitched is Keegan Thompson with 99.0 innings, whereas Taillon is already at 120 2/3 innings. Being able to sign a pitcher that eats innings will make the team better, even if his ERA is not as low as we would like.

Rich Hill

Similar to what Zack Greinke and Albert Pujols are doing now, it is not surprising when a veteran player goes back on a one-year contract to play for the team where their career started before riding off into the sunset. Rich Hill first came up with the Cubs to start his career in 2005, staying with them for four years. Eighteen years later, the 42-year-old seems like his career is close to being done, posting a 4.52 ERA in just 73 2/3 innings this season with the Boston Red Sox. If the Cubs are to sign Hill, it would likely be for bullpen depth or even on a minor league contract. It is also beneficial for the younger players to have a veteran on the team such as Hill, especially with Heyward being gone next season.

One thing’s for sure: Chicago will have plenty of options to choose from this winter. Come next spring, there will be new faces and old faces in camp down in Arizona. This offseason will help the fans understand what direction the Cubs are going in: are we destined for a more competitive team soon or taking a lengthier path on a journey back to relevance?