Cubs Offseason Overhaul: Restocking Rotation on Budget, Maybe with Familiar Names

Despite being the smallest unit on the roster, the Cubs’ starting rotation might be the hardest one to peg. That’s because 40 percent of it needs to be replaced and the market for legit starting pitching can get a little crazy. And crazy expensive, which isn’t something the Cubs really want to get involved in.

I’ve already looked at some options for the relief corps and for position players, but I wanted to save the rotation for last because it’s the most important this winter. Don’t expect the Cubs to follow my steps, though, since they’ll probably be looking to lock down their additional starters first in order to define the parameters of their overall offseason strategy.

…they’ll probably be looking to lock down their additional starters first in order to define the parameters of their overall offseason strategy.

With Kyle Hendricks, Jon Lester, and Jose Quintana forming a solid core, the task of locking down two more arms might not seem like a very daunting one. They’ve got Mike Montgomery perpetually waiting in the wings, which means perhaps only having to bring in one new face. And then there’s Jake Arrieta, who is still a possibility to return in free agency.

Except, yeah, it’s probably not going to work out that way.

Montgomery had a few really nice starts for the Cubs in various fill-in stints last season, but I think we saw that his stuff plays better in the bullpen (playoff performance notwithstanding). Theo Epstein more or less confirmed that during his end-of-year address when he said that Montgomery could vie for a spot in the rotation, but that the plan is for him to serve in the same capacity as he has the past two seasons.

Which brings us to Arrieta, whose departure has been nothing short of fait accompli since at least May of 2016. We could probably push that point of no return to the prior winter, when the newly-crowned Cy Young openly expressed disinterest in an extension and just repeated the mantra that he would be a Cub for at least two more years.

But when Stephen Strasburg inked a seven-year, $175 million deal early in the 2016 season, we saw a stark difference in the way Arrieta addressed his future.

“You want to be paid in respect to how your peers are paid,” Arrieta said. “I don’t think that changes with any guy you ask. It happens around baseball every year.”

And then he dropped the line that has dogged him ever since: Aces get seven years. It was pretty fitting at the time, but we’re about a year and a half removed from that statement and Arrieta is neither an ace nor in line for a such a long deal. Even so, he’s probably going to be able to pull down five-ish years at 25-ish million per, which is no small potatoes.

That’s not an unintended flaw, but a necessary evil of a rebuilding strategy that focused on bats. Lester was a special circumstance, now they’re in more of a short-term-value mode.

Given how many French fries the Cubs are going to have to make over the next few seasons, they may be worried about Arrieta’s 50-pound bag of russets sprouting eyes. I’m pretty sure that’s exactly what they’re worried about, at least metaphorically speaking, since they’ve already got one aging pitcher pulling down loads of cash.

Keeping with the grocery analogy, you could say the Cubs view pitching kind of like milk and bread. By that I mean they’re staples that need to be purchased frequently and are best not bought in bulk lest they go bad. That’s not an unintended flaw, but a necessary evil of a rebuilding strategy that focused on bats. Lester was a special circumstance, now they’re in more of a short-term-value mode.

That means avoiding the upper echelon of the pitching market — which includes Arrieta, Yu Darvish, and Masahiro Tanaka (if he opts out) — in order to focus on a few names from the well-stocked pool in the next few tiers. That makes both philosophical and financial sense, even if it’s not nearly as exciting as making a huge splash.

One name being bandied about a lot lately is Alex Cobb, who pitched for Joe Maddon in Tampa and who’s coming off of 179.1 innings in his first full season back from elbow reconstruction. He’s very solid, but his value is suppressed a little due to his age (just turned 30); medical history (TJS limited him to 22 innings between 2015 and 2016 combined, and all of those came in the latter); and his lack of really eye-popping numbers (only 6.42 K/9 and 4.16 FIP in 2017).

The pursuit of Cobb could be influenced, heavily so, by what happens with former Rays pitching coach Jim Hickey. With so many of his colleagues now out of work, Hickey has no shortage of potential destinations. But he’s interviewing with the Cubs Monday and has a good relationship with both Maddon and Cobb, so there’s a good possibility that a reunion could be in the offing.

As an added bonus, Cobb would easily take first place in the Cubs’ annual Eddie Butler lookalike contest at spring training.

Former Cardinal Lance Lynn is another possibility, and one that would provide a fitting replacement for John Lackey. Not only would he be coming from St. Louis, but Lynn has a no-nonsense approach and is fond of deadpanning the media. Like Cobb, he’s 30 years old and coming off of his first full post-TJ season, which could suppress his overall cost. Then again, MLB Trade Rumors had him just outside the top 10 in their most recent free agent power rankings.

As we saw most recently with Jason Hammel, the Cubs are not opposed to bringing back former players. There are several of ex-Cubs among the roughly 50 potential free agents hitting the market this year, some of whom could be serious targets. We can probably go ahead and rule out Brett Anderson and Matt Garza, but Trevor Cahill and Scott Feldman might be worth another look.

Another intriguing name is Andrew Cashner, whose greatest contribution to the Cubs was as the centerpiece of the trade that brought Anthony Rizzo from San Diego. It would be on some seriously full-circle isht to bring Cashner back into the fold, provided he’s not looking for too much of what comprises a majority of his surname.

Cashner could be the guy who serves in the role I had hoped the Cubs could when I wrote about the ‘pen, that mediocre former starter who blooms as a lock-down reliever.

Though the 31-year-old has lost a little velocity and doesn’t generate nearly the strikeouts as he once did (4.64 K/9 in 2017), Cashner can still touch the mid-90’s and doesn’t give up many home runs. Even though his injury history doesn’t inspire a ton of confidence, I’d be fine with him as a fifth starter.

Or — and here’s where things get really interesting — Cashner could be the guy who serves in the role I had hoped the Cubs could when I wrote about the ‘pen, that mediocre former starter who blooms as a lock-down reliever. Though he’s not necessarily what I’d call an elite strike-thrower, Cashner has shown flashes of being so. And a transition to a relief role might add a tick back to the heater. Mmmmm, sexy.

Since I’ve gone ahead and opened the door to the late-night Cinemax portion of the post, let’s do a quick fly-by on the idea of Shohei Otani pitching for the Cubs (I know, right?). Because he’s opting to come to the States prior to exceeding age and experience limits, he’s not eligible for one of those monster contracts his countrymen have gotten in the past. And because of the way international bonus pools are structured now, the Cubs aren’t severely hampered (I’m biased, but I think there’s some really solid info in there) even with their spending restrictions.

But not every name is imbued with as much intrigue as Otani, or even Cashner. The Cubs had been after Tyson Ross last winter and he’s available again after failing to show much of anything with the Rangers. He’d be strictly a flier, though, and not a serious hope for the rotation. Or what about CC Sabathia? Or Francisco Liriano? Maybe Jeremy Hellickson?

The idea here is that the Cubs have way more available pitchers to comb through than they have openings to fill, so the possibilities are…well, they’re not endless, but they’re definitely myriad. While they probably won’t come out of the Winter Meetings with a pair of pitchers that instantly assures them of a return to the World Series, they should easily be able to shore up the rotation and determine how to best allocate resources to their remaining weak spots.

That means making some trades, something I have intentionally avoided suggesting here. Moving some current pieces to land a young, controllable starter — Chris Archer will inevitably come up and the Cubs were linked to Detroit’s Michael Fulmer, who could be slightly cheaper after undergoing surgery in September to alleviate ulnar neuritis* in his right elbow — is well within reason. It’s just not something I want to try to delve into just yet and there’ll be plenty of time for that as the once we get into the last two months of the year.

For now, it’s all about having fun throwing around names that make sense for the Cubs given what we know about the market and the team’s appetite to spend.


*Not to be confused with either neurosis or neuralgia (both of which are most commonly associated with Alton Benes, father of Elaine and no relation to Andy), ulnar neuritis or cubital tunnel syndrome is an inflammation of the ulnar nerve that can lead to weakness or numbness in the hand. You probably know the ulnar nerve better by its more colloquial funny bone moniker, so just imagine that being irritated on a frequent basis when you exert yourself.

Fulmer underwent ulnar nerve transposition at the hands of the legendary Dr. James Andrews back in mid-September. Said surgery moves the ulnar nerve from behind the medial epicondyle bone to a new spot where it will not be irritated or pinched by the bone. Though it sounds pretty serious, it’s actually relatively common and Fulmer is expected to be ready by spring training.

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