Cubs Probably Fall Short on Tarik Skubal, Still Need to Get ‘Dude’

Raise your hand if you have any level of confidence in the idea that the Cubs will be willing to hand ace lefty Tarik Skubal what would easily be the largest contract in club history. Okay, I see one or two out there. Now keep them up if you think the Cubs’ offer, even if it’s massive in relation to their past deals, will be bigger than what one of their historically more free-spending big-market rivals will bid.

Yeah, I thought so. While there may yet be a Pollyanna with rose-colored glasses, even Jed Hoyer’s acknowledgement of his shortcomings on the pitching front wasn’t enough to inspire confidence that anything meaningful will change this winter. Between the truncated initial free agency period, the unknowns of the next CBA, and their general reluctance to play at the top of the market for premium pitching, adding one of the best arms on the planet seems anything but likely.

They’re going to need to add someone to strengthen the top of the rotation, though, as all five of their season-ending starters could be lost to free agency. Clay Holmes could be brought back even if he declines his $12 million player option as expected, and there should be at least two other starters coming back from injury. With how much they get from Justin Steele and whether Ben Brown‘s neck can handle that extra workload yet to be determined, however, external additions will be necessary.

The problem all season, and this is something I had noted a few times here and there, is that their rotation wasn’t built to win in the postseason. Sure, they added some groundball machines via trade, but the lack of whiffs and the frequency of home runs allowed meant they were relying way too heavily on that MLB-best defense. You can’t defend a homer, and giving up a lot of contact in general means some balls are going to land safely.

It’s also not good to have a bunch of mid-rotation guys who you’ve got to mix and match situationally. MLB Network’s Jon Morosi joined 104.3 The Score’s Spiegel and Holmes to talk about exactly that on Tuesday, pointing out what has become all too obvious to fans.

“I think on the pitching aspect of this, you need a little bit more swing-and-miss, you need probably a true No. 1,” Morosi said. “And they’re gonna honestly have to look at it and say, ‘Are we ready to go toe to toe with the New York Mets and maybe the Dodgers in the bidding for Skubal?’ I tend to think they will fall short, but that is the type of person — they are a Skubal away, in my opinion, a Skubal or a true ace away.

“And you can certainly hope that Horton comes back, et cetera, but you have to go get a dude if you want to credibly say you’re going to be a World Series team in 2027.”

A dude would indeed be nice, though Skubal is like Jeffrey Lebowski in that there’s no one else like him in this class. Not even close. Freddy Peralta and Trevor Rogers fall into the second tier, albeit one that is not immediately adjacent to Skubal’s. Then you’re probably looking at Sonny Gray, Kevin Gausman, and maybe Chris Bassitt (if he’s healthy). But at best, you’re talking about as many No. 2s as a colonoscopy prep.

Japanese righty Kaima Taira is a very intriguing option who has been on the Cubs’ radar for a while now, and he’s got high-end velo with an interesting approach angle that kept the ball in the yard over nine years in NPB. If uncertainty over his role in MLB suppresses his price, it’s easy to see the Cubs pursuing him and one of the starters above at a much lower combined cost than Skubal will fetch on his own.

Ah, but therein lies the problem. We’re back to the whole value thing and going with quantity over quality. Don’t get me wrong, depth is most definitely a requirement for an MLB team. No one knows that more than the Cubs, who had an entire pitching staff on the IL this season. There’s just a point at which failing to add that top player means limiting the potential for success.

Going into a postseason series crossing your fingers that your starters can get through 4-5 innings with the games still at least within your grasp isn’t an effective strategy. Yet that’s where the Cubs were with Gausman and Matthew Boyd, the former of whom still wasn’t fully recovered from a left shoulder injury suffered during his last start of the regular season. Maybe Horton could have been that dude, and maybe he can be in the future.

Thing is, maybe isn’t good enough for one of the largest markets in the world.