Here’s Who Theo and Jed Should Target in Free Agency this Offseason

With a significant amount of money coming off the books and a strong class of free agents, there’s multiple routes the Cubs can go to address their weaknesses.

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Although the Cubs had about as disappointing of a season as any fan could have expected, it should be well in the rearview mirror as far as the front office is concerned. And based on president Theo Epstein’s press conference on Monday, it is. To alleviate the problems that decimated the Cubs this past season, step one of the offseason was to part ways with Joe Maddon. While obviously not every fan will agree, take a look at this article I wrote about last week explaining why it is a wise decision. Next, onto free agent acquisitions. The Cubs, unlike last offseason, have a significant amount of money coming off the books. This comes at a perfect time for Theo Epstein and Jed Hoyer to induce significant, and quite frankly much needed, change to the roster. First, let’s look at all the expiring contracts and exactly how much annual salary is coming off the books.

As you can see, the Cubs have a lot of money to spend this offseason, and it’s peculiar why there hasn’t been much talk about it. I suppose the media is too busy hovering around all the news of Joe Maddon’s “firing”. However, this should not be overlooked, because what the Cubs do with this money will shape the next three or four years of the franchise. The front office cannot afford any mistakes, i.e. Tyler Chatwood, when spending this money in free agency. I’m going to start this off with a disclaimer because a good chunk of that money will be first used on Kris Bryant, Javier Baez, Kyle Schwarber, and Willson Contreras because of them all hitting arbitration, assuming the Cubs retain each of them. Since it’s ridiculously hard to value arbitration, I’m not even going to try.

With that said, let’s get into the four relevant team options (Anthony Rizzo has a team option of $16.5 million, but it’s not even worth discussing. It will be picked up). Brandon Morrow’s is $12 million (with a 3 million buyout), Derek Holland’s is $7 mil, David Phelps’ is $5 mil, and Jose Quintana’s is $11.5 mil. Morrow, Holland, and Phelps are all a no brainer: there is zero chance the Cubs pick any of these options up. This is because Duane Underwood, Brad Wieck, James Norwood, Adbert Alzolay, Alec Mills, and potentially Dillon Maples are all expected to move from the minors and become mainstays in the Cubs’ bullpen next year. On top of that, Kyle Ryan and Rowan Wick were highly productive this past season and return to the pen. These guys all have livelier arms and don’t have health issues (i.e. Brandon Morrow), making the decision easy. Plus, all of these farm system guys are on club friendly, cheap contracts. This means the Cubs will not have to go in free agency to replace all the bullpen’s expiring contracts. This allows Theo and Jed to spend more freely on solving other weaknesses of the roster, which I get into later in this article.

The last option, Jose Quintana, is much more difficult to assess. Before September, I would have said there’s a 100% chance this option is picked up. But after five appearances and a 11.09 ERA in September, the Cubs may move on from him and pursue better options in free agency. Quintana, Jon Lester, and Hamels’ downfall in the second half of the season is by far the main reason the Cubs blew up the way they did.


Duane Underwood Jr. is one of many young Cubs relievers that will be a main guy in a bullpen that will feature younger, livelier arms next season.

Speaking of starting pitching, there are a good number of guys in free agency that the Cubs could pursue, and it is far and away the team’s biggest need. You can talk all day long about how great Nicholas Castellanos was after his acquisition, and rightfully so, but without a significant upgrade in the rotation the Cubs will not compete for the NL Central crown next year. According to MLB.com, Gerrit Cole, Hyun-Jin Ryu, Stephen Strasburg (if he opts out), Dallas Keuchel, Zack Wheeler, Madison Bumgarner, and Jake Odorizzi are all expected free agents and viable options that the Cubs should consider. However, I don’t foresee every single one of these names getting away from their respective teams and entering free agency. I assume Gerrit Cole will, however, and he is somebody the Cubs should target immediately. With how free agent contracts have been structured lately, I don’t expect him to command anything unreasonable like contracts were 5-10 years ago. I expect him to warrant around $23-28 million a year, depending on longevity and incentives. There are obviously other big-name organizations that will be in the market for Cole, namely the Yankees, but the Cubs should do what they can to sign him. Cole led all starters in baseball in Wins Above Replacement, at 7.4, and strikeout rate, at 39.9%. He also had a 2.50 ERA, third in baseball, and an opponent batting average of .185, good for second among starters. Those are absurd numbers and, if it wasn’t for Justin Verlander being equally as dominant, he’d win the AL Cy Young in a landslide.

Although I believe the Cubs should go hard after Cole, there is a downside: they may need to let Quintana walk in order to sign Cole if they want to also address the team’s other weaknesses. Both Cole and Yu Darvish were among the top 3 in baseball in K-per-9 in the second half of the season. Cole was at 13.82 and Darvish was at 12.53. Starting pitching is a necessity for any team that truly wants to contend, and a 1-2-3 rotation of Cole, Darvish, and Kyle Hendricks is as nasty as it gets. Those three were among the 12 starting pitchers with the lowest hard-hit percentage in baseball. While Hendricks doesn’t strikeout nearly as many guys, he’s a lethal number three. I understand relying on Chatwood and Lester as the back end of the rotation is a risk, but it’s still worth it with how dominant those first three could be.


Although Yu Darvish emerged as an ace the second half of the season, Gerrit Cole is the type of elite level, number one pitcher that could turn the Cubs’ biggest weakness going into the offseason, starting pitching, into one of the team’s biggest strengths.

If the Cubs can’t make Cole work, Hyun-Jin Ryu and Strasburg are both aces that the Cubs should look to for the exact same reasons as Cole. However, I do not believe either are nearly as likely to leave their teams and hit the free agent market. A backup option the Cubs can consider is Zack Wheeler, whom I really like. I say “backup” because he’s not viewed as an ‘Ace,’ but he would be a very formidable 3rd starter. He’s been very good for the Mets the past two seasons, had a 4.1 WAR in 2019, and is only 29 years old. He’s the type of guy the Cubs could lock up as a middle rotation guy for three or four years. If that doesn’t work, Bumgarner, Keuchel, and Odorizzi are viable options for the same reasons. However, each of them has more red flags, whether that be age, inconsistency, or only having one good year thus far, in Odorizzi’s case.

Moving on from the rotation, the next task the Cubs should focus on is signing Nicholas Castellanos. His market value is ridiculously hard to assess because he was among MLB’s best offensive players in the second half of the season, but regression is almost assuredly going to happen next year. But, with a team best OPS of 1.002 and 154 wRC+, he needs to be signed if the annual salary asking price does not exceed $20 million. In addition to the statistical output, his locker room presence and mindset of playing every game like its opening day is exactly the type of energy this clubhouse needs to weed out the complacency that seemed to be pervasive in the clubhouse the past two seasons. Castellanos is the type of person guys rally around. He’s someone that you can build a team around, and the front office knows it. Theo spoke extremely high of him on Monday and said he would love to have him back next year, but admitted it is much more complicated than that.

There are many other mid-level moves the Cubs will make other than acquiring a starting pitcher and trying to sign Castellanos, but there’s no need to go down countless number of rabbit holes to try and predict all the moves that will happen. Veterans like Brett Gardner, Howie Kendrick, Jarrod Dyson, and maybe even a return of Ben Zobrist, are acquisitions that the Cubs will consider for outfield and middle infield depth. Regardless, there are significant weaknesses that the Cubs must consider as they scour the free agent market. According to FanGraphs, the Cubs had the worst contact percentage in baseball at 73.8%. That’s embarrassing. Also, they were sixth worst in hard hit percentage at 35%. Castellanos helps both of those factors, which is why he should be re-signed, but other moves must be made to sure up these weaknesses. On the defensive side, the Cubs were tenth worst in baseball at defensive runs saved (DRS) with -13 on the year. Remember the historically good 2016 defensive team that was paramount in the Cubs ability to win the World Series? Yeah, they had a DRS of +107, best in baseball. That is an astonishing gap. To be honest, that might have been the most glaring difference between these two teams, more so than any offensive statistic. Castellanos by no means helps that woeful defensive metric with his -9 DRS in right field this year, so a lot must be done to solve that weakness. Not having Joe Maddon at the helm constantly playing guys out of position will help immensely, though.

In a perfect world, the Cubs sign both Gerrit Cole and Nicholas Castellanos this offseason. I understand that is a very tall task and they may have to part ways with Quintana to do so, but Theo is known to make big risks when needed. He decided to do essentially nothing last offseason and run it back with this group. That decision failed miserably, so there will be many moves made this offseason to address pervasive holes on the roster. Starting with Cole and Castellanos as big splash signings, then rounding out the rest of free agency with mid-level signings to generate more contact and defensive prowess, is exactly the type of offseason this team needs in terms of free agency. Obviously, there will be some trades this offseason as well, as Theo mentioned on Monday. However, that’s an article for another day. Stay tuned.


Featured Photo: Phil Velasquez/Chicago Tribune

3 comments on “Here’s Who Theo and Jed Should Target in Free Agency this Offseason”

  1. Well prepared article and quite analytic. I have to comment with my opinion that it wasn’t the starters bad stretch that brought down the Cubs but the fact that hitting was not consistent. We took lotsa games to the 9th with a 1-run lead and bullpen blew it but before entering the 9th look at how many runners left on bases in order to get to that predicament. We need a star hitter a Rendon type of guy cause no matter how good the rotation is you cant always win 1-0 -we need hits.

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