Cubs Could Pursue Gerrit Cole This Winter, Not Among (Way Too) Early Favorites

With Cole Hamels hitting free agency, Jon Lester hitting a wall this August, and opponents hitting all the home runs off of Yu Darvish, the Cubs are certain to be in the market for starting pitching this winter. Hamels alone removes $20 million from the books, then you add in Brandon Morrow (whose guaranteed cost toward the CBT is already sunk), Steve Cishek, and Brandon Kintzler. With several league-minimum pitchers potentially stepping into full-time relief roles, the Cubs could spend big on a key piece or two.

Naturally, the way-too-early conversation turns to Astros co-ace Gerrit Cole, with whom the Cubs are quite familiar from his days with the Pirates. According to Buster Olney, Chicago “could be involved in the Cole bidding” (ESPN+ membership required) once the free-agency period opens at the conclusion of the season.

However, Olney tempers any expectations by saying “they’ve already got a lot of other dollars on the books” and does not list the Cubs among the top three suitors for Cole. Those would be the Phillies, Yankees, and Angels, all of whom have some degree of appeal or attachment to the flame-throwing righty.

Cole grew up in Newport Beach, not far from Angels Stadium, and might like the idea of moving back home. The Yankees not only drafted Cole out of high school (he opted to attend UCLA instead), but tried to trade for him before he eventually ended up in Houston. The Phillies have a good working relationship with Scott Boras and might want to effectively replace Jake Arrieta.

That’s perhaps a harsh way to look at it, but Arrieta, himself a Boras client, hasn’t worked out nearly as well as the Phillies had hoped. A procedure to remove a bone spur from his pitching elbow has shut him down for the remainder of this year and there’s really no way to tell whether and how effective he’ll be when he returns. Assuming the club doesn’t exercise its $20 million options in 2021 and ’22, next year will be Arrieta’s last in Philly.

Even with all that in mind, it’s a little premature to count the Cubs out. I mean, it’s way premature to be having these conversations in the first place, but we’ve already noted that the Cubs have a lot of money falling off the books. And that’s before mentioning Ben Zobrist. Then you factor in the substantial revenue bump they’ll receive once Marquee Sports Network flips the switch in February.

Cole figures to be the most coveted pitcher on the market and could command north of $200 million, so signing him would likely impact the Cubs’ appetite to spend big on extensions for Kris Bryant, Javy Báez, Anthony Rizzo, etc. It could also give them the best chance at squeezing the most possible juice out of the remaining competitive window that seems to be closing much faster than anyone had anticipated.

Consider this fair warning for what you’re going to hear ad nauseam this winter, especially if free agency plays out anything like it has the last two seasons.