Heading into the offseason the Cubs had a very specific “to-do list” when discussing how to improve the ballclub. Ask any Cubs fan and you’ll get different answers from each one on the direction the club should take.

Is it David Price the Cubs need or is it a trade for a young arm? Is it Jason Heyward to a mega deal or Denard Span to a stopgap , short-term contract? These, and many others,  have been the constant water cooler conversations happening in Wrigleyville since the  Mets exposed the weakness of the Cubs middle rotation in a 4-game sweep not even 2 full months ago. 

So what do we think the Cubs need to do next? Well, first, I think we should look at some of what Theo stated in his postseason press conference: 

“we’d like to add at least one quality starting pitcher this winter.”

That was step one. The Cubs achieved that with their perfectly timed signing of John Lackey on Friday evening. Inking the former Red Sox and Cardinals starter to a 2 year, 32 million dollar contract, which will likely end up being the greatest value of any free agent pitcher signed in this market.

But Theo didn’t say he wanted only one quality starter. No, he said at least. The Cubs have been linked to every major pitcher believed to be available through free agency or trade. There are options out there but it will not be cheap. The only question is what type of currency are the Cubs wanting to pay? Monetary or prospect?

Theo also stated in that press conference that the ball club needed to improve specific aspects of their lineup offensively: 

“I think we can get better as a situational hitting team and as a contact hitting team”

As well as a desire to shore up their defensive weaknesses:

“Controlling the running game will be a big emphasis in spring training. I think we could generally improve our outfield defense”

So where does that leave us? Ah, yes! One more pitcher, likely a CF that will be an improvement defensively and improve the teams contact rate, and perhaps an improvement in controlling the run game. Got it. 

So, after signing John Lackey what are some options that make sense at pitcher? 

2015: 3.04ERA/3.45FIP/4.07xFIP /3.4 WARP

2016 Projection: 4.07 ERA/ 4.07 FIP/ 1.7 WARP

The Cubs were rumored to have the foundation of a deal worked out with the Braves for Shelby Miller before the Braves apparently took him completely off the table on Wedesnday night.

I am not disappointed that the trade did not materialize. I have not been as high on Shelby Miller as some are. Projections are not the end all, but of the potential trade targets the Cubs have been linked to Shelby Millers 3.20 BB/9 innings is the highest and 7.75 K/9 innings one of the lowest. 

His main selling points are that he had a solid year last season, he is under control through 2018, and he is only 25 years old. All of which are solid selling points.

The only question is, is that enough selling points to ignore the high walk rate and low projections and include either Soler or Baez in a trade for him? Because that’s what it would take.

2015: 3.63 ERA/ 2.84 FIP/ 2.64 xFIP/ 4.8 WARP

2016 projections: 3.04 ERA/ 2.96 FIP/ 4.8 WARP

I love Carrasco, and have been big on the Cubs getting him for a while. He is fully entrenched in his prime at the age of 28. Similar to Jake Arrieta, he was a late bloomer. Because of this, he only has 556 innings pitched on his arm thus far.

As you can see, Carrasco had a terrific season last year. While his ERA was higher than Miller’s, his FIP and xFIP were significantly lower. He also struck out more than 10 batters per 9 innings while waking less than 3 per 9. All of those peripherals bode well for sustained success as you can see in the projections.

Just as importantly, Carrasco is not just under control through 2020(his prime seasons), but his total contract is roughly 40 million. To put that in perspective, Jordan Zimmermann, who is projected to have 2.5 WARP next season and has logged significantly more innings, just netted 22 million per year over 5 seasons. Carrasco may end up being the biggest bargain in baseball throughout the course of his contract.

I would be okay if the Cubs considered BOTH Soler and Baez OR Soler and top prospect Gelyber Torres in a deal for Carrasco. This is why we created redundancy and depth at certain positions throughout the organization. To not be reliant on a free agent pitching market that is becoming more expensive by the day.

Free Agent Targets:

We covered span in our potential Black Friday value article. Span would check all of the boxes on the offensive and defensive side of the ball. He has a career .352 OBP, a career strikeout rate of only 11%, and a career Defensive rating of 31.1 per fangraphs. He also would not cost the Cubs another draft selection to sign.

The question with Span is not his body of work, but his health moving forward. 

His season was cut short due to a hip injury that inevitably required surgery. He will be 32 when the season begins and a hip injury is tricky. As we discussed in that same article, the hips are critical to creating torque as a hitter. With Span having a career .320 BABIP, creating torque is why he can drive the ball with such force throughout the field.

If Span is unable to create the same torque then what used to be hard-hit, line-drives to the outfield may become weak grounders in the infield. 

If the Cubs believe he is healthy then he may be a nice value signing on a 2 year deal.

Heyward will be expensive. He may be 200 million expensive, and the Cubs would have to get creative either through trade or with the structure of his contract to make that work. If they can, however, Heyward is a rare sight to see in free agency. He is a potentially elite talent available that has yet to enter his prime. 

Heyward would likely come in to play CF this season and move over to RF once Almora is ready to take over at Wrigley. 

On the field, Heyward provides elite defense, contact skills, and on-base ability. Since entering the big leagues in 2010 he has been good for 27.8 WARP. Each season he has decreased his strikeout rate while maintaining a BB% of roughly 10%. If he continues his trajectory, a 20/20 or 30/30 player that gets on base at a .360+ clip and plays elite defense is quite possible.

And about that 200 million dollar contract. With the contracts in baseball ballooning at a rapid rate, that could likely be a value contract within 3 seasons. 

Bryce Harper will likely sign a contract between 350-400 million dollars either by extension or free agency in the next few years. If you believe that Heyward is an elite-type player in his prime, now is the perfect time to stretch the budget to lock him up. By 2020 a player of Heywards skill set will be approaching a mind-boggling half-billion dollar total contract amount. 

Those economics are another reason why the Cubs should consider paying the high-price for a pitcher like Carrasco, as well. 

Heyward would balance out the lineup nicely as he can slot in anywhere from the leadoff spot down to the 5 or 6 spot in the batting order. If the Cubs can find a way to make it work, I love the idea of Heyward on this team through his prime. It also will pour a little salt on the John Lackey wound we just marked the Cardinals with.

There are many other players that make sense. 

Gerardo Parra could be a potential value signing that can also play CF this season.

Nick Markakis is a player the Cubs could negotiate coming back in a deal with Atlanta if they go that route to acquire pitching. 

Wei-Yen Chen is another free agent option to solidify the rotation. Though I am not convinced the Cubs are wanting to sign two free agent pitchers in this market. Regardless of rumors. 

The Cubs are also rumored to be seeking out a top closer wth names such as Ken Giles, Sean Doolittle, and Brad Boxberger being thrown around. 

That would give the Cubs a potentially elite bullpen. And there are two ways to improve starting pitching. Improve your rotation, or shorten the game by improving your bullpen. 

It’s finally that time. The 2015 Winter Meetings are set to begin!

Don’t forget to join the conversation at CubsChat.com throughout the winter meetings by using the hashtag #CubsWinterMeetings when you post, tweet, or Instagram. Every night we will pull the hashtag to give everyone a pulse of Cubs nation as the news comes out of Tennessee.