Chicago Cubs Rumors: The trade deadline has passed, what does free agency look like?

The Chicago Cubs have a good roster of players that are locked up for the 2024 season, but who could they target this winter to put together a dynasty?
Patrick Gorski-USA TODAY Sports
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Position Four: Starting Pitcher

Players available (alphabetically):

Lucas Giolito
Sonny Gray
Aaron Nola
Shohei Ohtani
Eduardo Rodriguez
Blake Snell
Marcus Stroman
Julio Urias

We’re going to work under the assumption that Marcus Stroman doesn’t re-sign, Drew Smyly doesn’t have his option picked up and Kyle Hendricks does have his option picked up. The Cubs will go into December with an expected rotation of Justin Steele, Jameson Taillon, Kyle Hendricks, Hayden Wesneski, and Ben Brown with those last two rotation spots very much up for grabs.

Lucas Giolito is going to be an expensive player based on name value. There will be people in Chicago that want to see him back, but this time on the North Side but I’m just not seeing the value. He’ll be entering just his age-29 season, but his career-best ERA while pitching 50 or more innings was 3.41. That’s awesome as a three or a four in a good rotation, but he’s going to get ace money and I just can’t abide that kind of money for a pitcher like this that has been coasting off of prospect status for the better part of eight years. 

Sonny Gray is one of my ideal targets this offseason if the Cubs don’t go big for one of Stroman/Urias/Ohtani/Nola. He’s a ground ball pitcher and the Cubs have put together arguably the best infield defense in the league, so let’s play to that strength. He’s currently making around $16 million with the Twins and I’d expect him to sign a deal for an equivalent amount due to his advanced age being offset by his All-Star status this season. Plugging him in with Taillon and Steele gives the Cubs three guys that would be third in the rotation on really good teams and would be second in the rotation on mediocre teams. I wouldn’t say any of them are aces, but having three guys of that caliber would be huge.

Aaron Nola will be expensive. He’s been a fine pitcher for the last nine seasons and he’ll enter his age-31 season expecting to get the big payday. If he’s smart, he’ll wait it out and sign after Ohtani and Urias have signed so that he and Stroman can split hairs over which of them is the best remaining starter. The money that it would take to sign Nola likely wouldn’t be too different from what it would take to sign Stroman, so the homer in me says to save the money and go with Stroman over Nola.

There’s not much to say about Shohei Ohtani that isn’t already known. If you have watched him play and you don’t say that he’s the best baseball player of all time then you’re wrong. I hesitate to throw out statements like that often, but if you believe Mike Trout or anyone prior to 1950 had more of an impact on a baseball game than someone that threw a one-hitter in the first half of a doubleheader and then came back to hit two homers in the second half then you can stop reading now. That being said, the rumors are that Ohtani wants to be a winner on the West Coast and at the moment the Cubs don’t check those boxes.

Eduardo Rodriguez and Blake Snell are in the same monetary areas as Stroman and Nola but they come with a little more risk due to injury history. The biggest thing they have in common is that both of them have pitched exceptionally well this season as they’re on their way to free agency. If the Cubs swing and miss at Stroman and Nola, I find myself liking E-Rod slightly more than Snell because he managed to shut down the Dodgers' attempt to add him at the deadline with just an hour left for the Dodgers to find another alternative which is legendary. 

The final player available would be the second most attractive realistic target the Cubs could go after which is Julio Urias. He just turned 27, so he’s the youngest player on this list because he started playing for the Dodgers in 2016 at age 19. He’s carried a career 3.08 ERA, he’s left-handed and his stuff is absolutely filthy. If the Dodgers add Shohei they’ll likely be out on Urias which opens the door for everyone else to add a legit young(ish) ace.

Decision: In the best-case scenario, the Cubs add Shohei Ohtani and start flying the World Series flags. However, a more realistic case is that they add Julio Urias and Sonny Gray and go into next season with a rotation of Urias, Steele, Gray, Taillon, and Hendricks. That would likely take a $200+ million dollar investment in Urias and at least a three-year $48 million dollar commitment to Gray. The Cubs are in the third-largest market in the United States, they’re allowed to spend. Let’s do this.