With Cody Bellinger opting in and the lineup pretty much set for the Cubs this winter, I knew there wouldn’t be much available regarding the team upgrading offensively. Thus, their dream scenario always had no choice but to add a top-end starting pitcher and bullpen help because it’s the best they can realistically do this winter. That reality quickly became the belief of the team’s intentions in the windy city.

Speaking of that starting pitcher, you can likely lock in Roki Sasaki high up on the teams wishlist this winter, but competing with the Dodgers for his services will be tricky, even if the team does have good relations with Japan in player recruitment. There are, however, multiple paths to acquiring another ace-level arm in the rotation, and Sasaki is the only option.

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Roki Sasaki can only sign a minor-league contract with a team this winter, given that he is only 23 years old. Therefore, he costs a major league club virtually nothing to sign him as a “minor-leaguer” and bring him directly to the majors. Given that relationship with Japan in recent years (Seiya Suzuki, Shota Imanaga), Hoyer will do all he can to bring Sasaki to the north side this winter.

Playing for a team like the Dodgers is enticing, especially given that they also have the same relationship with NPB regarding signing players out of Japan. They are also perennial World Series candidates, which makes swinging Sasaki to the Cubs a bit more problematic for Hoyer and the team’s front office. Still, he’s the cheapest option on the market regarding production from a dollar standpoint. If Hoyer can swing him away from L.A., the Cubs’ playoff chances in 2025 will skyrocket.

3 Cubs paths to an ace – 2. Trade (think Seattle)

The Cubs shouldn’t stop at Sasaki even if they are fortunate enough to land him. Still, until Sasaki signs with the team, the Cubs must continue to build rapport and be ready to strike. The Seattle Mariners have made it known they are willing to trade from their pitching depth and want infielders. The Cubs, who have eight top-100 prospects in their farm system, far and away, can offer the Mariners the best deal of any ballclub.

Logan Gilbert or George Kirby should be the number one for the Cubs this winter. If Seattle decides to trade, they will likely wait until the top free agent’s names are off the board so that the teams who missed out will create a bidding war for one of their guys. Still, it will be hard for any team to match an offer by the Cubs, who have prospects at their disposal and no one to play them in the majors.

On top of that, Cubs Chairman Tom Ricketts has stated he is okay with letting Hoyer play out the final year of his contract in 2025 without discussion of an extension, meaning the writing is on the wall if Hoyer fails to deliver the Cubs to the postseason this winter. It’s in Hoyer’s best interest to utilize some of his revamped farm to acquire major league-level talent. Now is not the time to be gun-shy to pull off a blockbuster trade.

If the Cubs cannot land Sasaki and an elite arm via trade, the worst-case scenario is you still have money to spend to land someone in free agency. At this point, the Cubs are uncomfortable with Corbin Burnes’ price, but a Max Fried coming in at a little bit cheaper may be something Hoyer entertains with his back against the wall.

In recent years, the Cubs have taken the meticulous approach of analytics and underlying sabermetrics to determine how they can save a buck while winning ballgames. They must stop acting like the Oakland “Moneyball” Athletics and flex their financial might. I believe Hoyer will surprise Cubs fans this winter by getting aggressive. He has no other choice if he wants to ensure he’ll remain the team’s President of Baseball operations for the foreseeable future.