The Chicago Cubs were contenders for a majority of the year, largely because they had a really good pitching rotation. Shota Imanaga looked like one of the best offseason signings in the league and their trio of Jameson Taillon, Javier Asaad and Justin Steele looked solid as well.

But it wasn’t enough to put them in the postseason, which is completely out of character for a Craig Counsell-managed team. Counsell has no intentions of repeating this failure in 2025 and the front office could look to build the team around a star-studded pitching rotation.

While their rotation was good, it has the potential to be great. There are a few free agents available this winter that could slot in and be huge pieces of a Cubs World Series championship in 2025.

What would the Cubs dream Opening Day starting rotation look like in 2025?

For more news and rumors, check out MLB Insider Robert Murray’s work on The Baseball Insiders podcast, subscribe to The Moonshot, our weekly MLB newsletter, and join the discord to get the inside scoop between now and the MLB offseason.

Cubs land Corbin Burnes to replace veteran Kyle Hendricks

While the Cubs won’t be in on a signing like Juan Soto, I wouldn’t count them out of signing the $200 million free agents a tier below Soto. This includes the likes of Pete Alonso, Willy Adames and Corbin Burnes.

Signing Burnes to reunite with Craig Counsell in an attempt to take down the Milwaukee Brewers would be poetic. A year ago, Milwaukee traded Burnes to Baltimore rather than looking to re-sign him. Now, he has the chance to reunite with his former manager and take down the front office that gave him away.

Burnes would sit perfectly at the top of the Cubs rotation. The righty would once again compete for NL Cy Young awards each year, just like he did when he was a member of the Brewers.

The issue here is getting Burnes to sign. Right now, Burnes’ free agency seems to hinge on what happens with Soto. If Soto signs with the New York Yankees, Burnes is likely to land with the Mets as Steve Cohen’s backup plan. If the Mets miss on Soto, they will throw way more money at Burnes than anybody else in the league can afford.

But Chicago still has a chance to sign Burnes, especially if they’re very aggressive very early in free agency.

Each team in the league is going to try to sign international superstar Roki Sasaki. Every single team in the league would have Sasaki in their dream starting pitching rotation.

Sasaki is coming over from Japan as a 23-year-old international free agent which means he can only sign minor league deals this offseason. That leaves the door open for any team in baseball to land him, which is unheard of for such a talented arm.

For Chicago, they have a little bit of ammunition to their negotiations with him. They can offer the ability to win now and in the future while also being able to pair Sasaki next to another Japanese star, Shota Imanaga, at the top of the teams rotation. Imanaga will be a huge piece to getting Sasaki to the Windy City this winter.

Acquiring Sasaki means Chicago would need to clear room by getting rid of either Jameson Taillon or Javier Asaad. While they’re close in production, Asaad is younger and cheaper, so dealing Taillon away would cut some cap while acquiring more prospects.

Imanaga, Steele, Asaad remain cornerstones of Cubs rotation

After adding Sasaki and Burnes in this scenario, the Cubs would also continue to lean on the three-headed monster of Imanaga, Steele and Asaad as they head into 2025.

This trio of starters was so good for Craig Counsell and the team last year that there’s no reason any of them should be moved, shopped or anything of that sort. For these three, it’s about getting to spring training in the best shape possible with their arms in the best condition possible.

It’s not a fancy move or a huge signing like the other two players on this list, but it’s arguably the most important thing that Chicago can have happen going into the 2025 season.