What Will We See from Cubs During Winter Meetings?

After weeks of inactivity, MLB’s offseason was kickstarted Friday by Shohei Ohtani’s decision to join the Angels. The Giancarlo Stanton trade threw gas on the burgeoning fire and you can bet several logs will be tossed on this weekend as the Winter Meetings get underway.

The Cubs have been quiet thus far, though signing Tyler Chatwood puts them ahead of most teams when it comes to important offseason transactions. But after missing out on Ohtani and with several holes left to fill, Theo Epstein and Jed Hoyer are going to need to get to work in Orlando.

Not all of their goals will be accomplished over the next few days, of course, but the Cubs are likely to add to the roster while laying the groundwork for future moves. I know, I know, that’s really generic. Let’s look, then, at some specific targets and options.

The rotation

The notion of trading for Chris Archer has been around so long it can now stand up on its own like an old pair of unwashed sweatsocks. Cubs fans have wanted a do-over on the trade that sent him to Tampa almost since the moment the ink was dry on the deal. Trouble is, the Cubs would Likely be rawked by the transaction cost.

We don’t know what the Rays’ ask would be, but all indications are that it’s somewhere between a buttload and a king’s ransom. I realize not all of you are well versed in all this advanced metrics mumbo-jumbo, so let me put that in layman’s terms. Prying Archer away from the Rays would probably take two of the following: Kyle Schwarber, Addison Russell, Javy Baez, Albert Almora Jr, Ian Happ, Victor Caratini. Maybe more.

An argument can be made that Archer is the best of the bunch when it comes to controllable starting pitchers who could be had, so there’s valid reason for the high cost. But as far as the Cubs are concerned, I think such a move smells about as good as those socks I just mentioned.

The cost alone is a huge factor and I’m not convinced Archer is that elite No. 1 starter who can make up for it. Unless he is, and maybe not even then, his added value alone isn’t enough to put the Cubs over the top. You can’t convince me that acquiring Archer versus signing Pitcher X is the move that really seals the Cubs’ return to the World Series. All that said, it’d be silly for them not to at least check in on their former farmhand.

Theo Epstein and Jed Hoyer will also be talking to Jake Arrieta about a possible return engagement, though I can’t imagine it’ll be much more than professional courtesy. The two sides are well apart in terms of both money and years and the only real chance for them to work something out would come if the bottom drops out of Arrieta’s market.

We don’t know exactly where that market sits, but we can make an educated guess that it’s around $25 million AAV for at least five years and we know that several teams have inquired as to the former Cy Young’s wants. The Nationals are one such team and they are very familiar with both Scott Boras and ace pitchers, so there are some serious connections there. Maybe the Cubs can get really creative with some kind of deferred compensation, but it doesn’t seem likely.

Alex Cobb is another starter who’s been tied to the Cubs for quite a while, though he’s also been mentioned in connection with the Yankees. And if the Cubs really want him, they’re probably going to have pony up north of $60 million over four years. Jon Heyman actually had it at 5/$75M in his projections, which seems a little salty. A lot salty, actually. Cobb has professed an affinity for Joe Maddon and Jim Hickey and I’d like to think $16 million AAV gets it done.

The issue here, and it’s not a small one, is that the Cubs would then be in for nearly $30 million per season on two guys with three Tommy John surgeries between them. The moves could really pay off and give the Cubs a very solid starting five or they could implode spectacularly. Or they could just be meh.

There’s also the possibility of going after Lance Lynn or Jhoulys Chacin, the latter of which would make our own Brendan Miller very happy. Chacin raised his profile a bit after a good season in pitcher-friendly Petco Park, but he still figures to command less than $10 million per. With better pitch sequencing — looking at you, Hickey — the 30-year-old righty could be an excellent short-term investment.

The bullpen

In stark contrast to the market for their starting brethren, relief pitchers are quite plentiful this winter. We’ve been hearing about former Dodger Brandon Morrow for a while, but the Cubs have also been linked to former Twins closer Brandon Kintzler of late. Then you’ve got Jake McGee, Addison Reed, Bryan Shaw, and a whole host of other possibilities.

I’d love to see the Cubs convince Andrew Cashner to return to Chicago in a relief role a la Kerry Wood, though that sentiment may not be shared by either the team or the player.

As with Arrieta, there’ll be talks with Wade Davis on reprising his role as shut-down closer. But just like his qualifying-offer counterpart, Davis is sure to be in high demand and may end up pricing himself out of the Cubs’ comfort zone. And with Dillon Maples and Carl Edwards Jr. potentially waiting in the wings, it’s not likely we’ll see a departure from the previous unwillingness to pay big for the volatility of a late-inning reliever.

One other possibility is Rays closer Alex Colomé, who is projected to earn $5.5 million in his first arbitration-eligible season and is said to be available in a trade. That’s cheap for a closer and he’s under club control through 2020, but the rising cost is something Tampa would like to shed. If they can land some serious talent in return, all the better.

The Cubs would have to feel pretty good about Colomé maintaining that 0.54 HR/9 while also moving his 7.83 K/9 and 3.11 BB/9 in opposite directions. That’s a bit of a gamble when you consider that the return probably includes one of the players we mentioned in an Archer deal, since this is a case of the Rays throwing lines in the water and trying to max their value. I don’t see it happening, but it can’t hurt to check in.


I believe the Cubs will come out of the Winter Meetings with another starter and at least one more reliever, though your guess is as good as mine as to who those guys will be. If pressed for predictions, I’d put Cobb and Morrow out there simply because we’ve heard both mentioned so many times.

Epstein and Hoyer have both talked about how they need to be open to the possibility of trading young talent from the 25-man roster, but that doesn’t mean they’re going to do it. The return needs to make sense relative to what they’re giving up and why. And even though the goal is to remain competitive, the Cubs may not need or want to go all-in this offseason.

Whether you want to read that as saving up to go after Bryce Harper next winter is up to you. More than anything, I believe the Cubs want to avoid overspending from their main resources just because this down market would force them to do so. Or maybe I’m wrong and they flip some of their position players for pitching. Anything’s possible.

In the end, I believe the Cubs are going to be very active and will be doing a lot of talking to various parties, but that their moves will mainly be of the garden variety. Which means they’ll make two huge splashes and make me look like an idiot.

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