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jon lester feature red soxAs I said before when this came up, the only thing you can really take away from any prediction that has the Chicago Cubs signing both of the top starting pitchers this year, Jon Lester and Max Scherzer, is that the baseball commentariat believe the Cubs have a ton of money to spend and a ton of desire to add impact starting pitching. They are not wrong in that regard, and I’d even go so far as to say that they’re probably right that the Cubs have interest in both starting pitchers. But I really have trouble getting on board with the idea that there’s a realistic chance the Cubs actually sign both.

But, just as it was for Andy Martino at the New York Daily News, that’s the prediction the typically-grounded Ken Davidoff is making at the New York Post. Davidoff made his projection earlier in the week, and, given the label I slapped on Martino’s prediction (fun, but probably nuts), I wasn’t going to troll for clicks by again discussing the unlikely scenario. But Davidoff wrote some actual thoughts about his prediction, and noted that the double-dip was actually suggested to him by an executive in the game. (A second executive, however, told Davidoff it was unlikely after he’d made his original prediction.)

Davidoff believes that Lester will sign early, with Scherzer lingering on the market for a while (not an atypical guess for a Scott Boras client). The longer Scherzer hangs around, Davidoff’s thinking goes, maybe the Cubs decide to pull the trigger later in the offseason and really go for it in 2015.

Given where I think payroll is going to land for 2015 ($100 to $110 million), I don’t think signing Lester and Scherzer is in the financial cards. I’ll concede that I was probably conservative with that projection, and backloading can make just about anything possible. If the Cubs were supremely confident that their upcoming TV deal was going to afford them perverse loads of revenue by 2019 (or maybe sooner), and if they were sold that both Lester and Scherzer are highly likely to age well, then I suppose there’s a small chance that they could try to land both pitchers.

… but I just don’t buy it.

And, given the risks associated with pitchers after age-30 and the concerns I have about failing to stagger these kinds of contracts, I’m not really sure I’d want the Cubs to get both guys. Sure, it’d be a ton of fun and would make 2015 even more exciting – but I’m not sure it’s the right long-term strategy, especially when you consider just how much pitching is going to be available over the next 15 months.

In the end, what I do buy is that the Cubs will pursue each pitcher in the sense that they’ll talk to them and their reps, and try to sign them – with a preference for one, and a fall-back to the other. James Shields is interesting to include in this discussion, given that he could wind up getting a smaller contract, and maybe there’s a tiny chance the Cubs could land both a Lester/Scherzer and a Shields. I’m dubious on that one, too, though, and tend to think Shields is another fall-back option.

For me, the ideal pitching offseason would involve the Cubs getting one of the top tier arms, one of the better second tier arms, and also picking up a lottery ticket (like a Brett Anderson). That’s essentially what the Cubs, themselves, have said they’d like to do. From there, you go into the 2015 season with a competitive rotation, and could bolster it even further after the 2015 season with a tremendous class of arms from which to choose.

But, hey – if the Cubs are projecting crazy money in the future and want to start spending that way? It’s not like I’m going to be angry if they signed both Lester and Scherzer. I just don’t see it happening, or even realistically being considered.

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