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Cubs New Year’s resolutions, No. 1: Make big deals

Pitchers and catchers report in 40 days

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Cody Bellinger rounds the bases after a double at Wrigley Field in September
Photo by Quinn Harris/Getty Images

It’s January, and like many people I spend the first weeks of every New Year evaluating what went right in the previous year(s) before setting intentions for this year. I see no reason this practice should be limited to individual fitness, writing and self-improvement goals so I decided it was a perfect time to set some Cubs New Year’s resolutions. This is part one of a series that will continue through January. Some of these resolutions will be aimed at the front office, others will be geared towards the coaching staff, all of them will be of interest to the fans who love this team. Feel free to join in with your Cubs New Year’s Resolutions in the comments.

Make a big deal

The Cubs were the only team in MLB that had not added a single MLB player to the 40-man roster this offseason, until this minor deal Friday afternoon:

It’s a stunning state of affairs for a team that missed the playoffs by one game in 2023 approximately 40 days before pitchers and catchers report. It’s particularly unexpected after the Cubs made one of the boldest additions to their coaching staff early this offseason signing Craig Counsell to the largest ever managerial contract in early November. It’s especially galling because the team lost at least three key players to free agency in Cody Bellinger, Marcus Stroman and Jeimer Candelario.

Counsell’s wisdom might bring some additional wins to the North Side of Chicago, but there is no manager worth all of the wins those three players contribute to a club. So the first thing I’d like to see the Cubs do is shed whatever reticence has kept Jed Hoyer from making big deals.

There are a number of reasons this offseason has been slow for the Cubs, but I think Patrick Mooney really summed it up well in this piece in The Athletic. The free agents who are currently the best fit for the Cubs are almost all represented by Scott Boras and he’s perfectly fine waiting out the market until he gets the deal he thinks his clients deserve. Jed Hoyer, on the other hand, seems particularly cautious on deals with a lot of years and high AAV. It’s a perfect storm for an impasse:

There are a few explanations for the inactivity surrounding the Cubs. The baseball industry intently focused on Shohei Ohtani and Yoshinobu Yamamoto for most of December only to watch a very predictable ending — the Los Angeles Dodgers signing both Japanese players for more than $1 billion. Cubs president of baseball operations Jed Hoyer is a more measured executive than his predecessor, Theo Epstein. A multiyear rebuild has given the Cubs several core players, some more internal options and the prospects to seriously explore trades.

Boras is also a factor because he’s so comfortable taking his clients into January or February before making deals. Jake Arrieta, the last Cubs pitcher to win a playoff game, didn’t sign his three-year, $75 million contract with the Philadelphia Phillies until March 2018. That patience means it’s unrealistic to think Cody Bellinger will suddenly start prioritizing early opt-outs and short-term deals, according to a league source.

Besides Bellinger, the former MVP who thoroughly enjoyed his comeback season with the Cubs, Boras represents a group of players that includes Gold Glove third baseman Matt Chapman, first baseman Rhys Hoskins and designated hitter J.D Martinez. Bringing back Bellinger would only be a first step toward getting back on the playoff bubble as the Cubs could use an additional hitter to build out a lineup for October.

The piece goes on to note that most of the starting pitchers of interest to the Cubs are also represented by Boras, including Jordan Montgomery, James Paxton and Sean Manaea. It’s a great piece and you should read the whole thing, but allow me to be a bit more blunt than Mooney.

The largest free agent contract in Cubs history is still the eight-year $184 million deal the Cubs inked with Jason Heyward prior to the 2016 season — and it busted. This is not a slight to Heyward. Long-term readers of this blog know I think he earned every penny of that deal with whatever he said during the Game Seven rain delay in Cleveland, his defense on the field and his leadership in the Cubs clubhouse. But from a baseball offensive production v. dollars paid standpoint, the Cubs did not get what they expected from Heyward. Hoyer seems particularly reluctant to be the guy who dishes out the next largest deal in Cubs franchise history only to see it bust.

The problem for the front office is that the market has continued to accelerate in the seven years since the Cubs made their largest move ever. Take a look at the largest deals in MLB history as of this winter and realize just how far away the Cubs are from this list:

1. Shohei Ohtani, Dodgers: 10 years, $700 million (2024-2033)
2. Aaron Judge, Yankees: 9 years, $360 million (2023-31)
3. Bryce Harper, Phillies: 13 years, $330 million (2019-31)
4. (tie) Corey Seager, Rangers: 10 years, $325 million (2022-31)
4. (tie) Yoshinobu Yamamoto, Dodgers: 12 years, $325 million
6. Gerrit Cole, Yankees: 9 years, $324 million (2020-28)
7. (tie) Manny Machado, Padres: 10 years, $300 million (2019-28)
7. (tie) Trea Turner, Phillies: 11 years, $300 million (2023-33)
9. Xander Bogaerts, Padres: 11 years, $280 million (2023-33)
10. Alex Rodriguez, Yankees: 10 years, $275 million (2008-17)

Now, I’m not here to pretend that the Xander Bogaerts deal is going to end well for the Padres, but the Bryce Harper deal looks pretty solid at this moment in time four years after it was finalized. Whether you love some of these deals or hate them, it is a problem that the Chicago Cubs aren’t anywhere close to this top 10 list. In fact, check out the top 20 contracts of all time on MLB Trade Rumors, because the Cubs aren’t close to that list either.

It gets even worse when you look at this list of the top free agent contracts & extensions for each club compiled by Sarah Langs. The following clubs all have at least one free agent contract that is larger than the largest contract in Cubs franchise history: The Boston Red Sox, New York Yankees, Minnesota Twins, Detroit Tigers, Los Angeles Angels, Seattle Mariners, Texas Rangers, Washington Nationals, Philadelphia Phillies, Arizona Diamondbacks, Los Angeles Dodgers and San Diego Padres. When you take extensions into account, the Cubs are also lagging behind the Atlanta Braves, New York Mets, Miami Marlins, Cincinnati Reds and Colorado Rockies. That’s 17 teams who have all committed more years and dollars than the largest deal the Cubs have ever signed.

This seems like a great time to remind people that attending a Cubs game is the priciest experience in MLB.

Free agents still available (and projected contracts)

With all of the above in mind let’s take a look at some of those free agents who Patrick Mooney mentioned along with the possible contracts they could demand. For each of these players I’ll include three contract predictions for comparison. MLB Trade Rumors, The Athletic and FanGraphs have all speculated on the deals these players could demand and comparing those contracts is a better source of information than relying on only one set of predictions. One note before we get started — the FanGraphs numbers report a prediction by Ben Clemens and both the median and average crowdsource results. I’ll be using Ben Clemens’ estimate below.

Cody Bellinger
MLB Trade Rumors: 12 years, $264 million
The Athletic: six years, $144 million
FanGraphs: six years, $150 million

Bellinger did exactly what he needed do with his one-year reset on the North Side of Chicago. I’ve already written about what went well and where the question marks live. It’s undeniable that he fits on the Cubs roster and in their clubhouse, we all just watched it, with our own eyes.

Beyond the questions of whether Bellinger’s bounce back season was real or not, I think there are two other potential hold ups on a Chicago and Bellinger reunion. The first is that Bellinger’s primary position is centerfield, where Pete Crow-Armstrong looks ready to take over defensively at some point in 2024. However, Bellinger’s secondary position is first base, where the Cubs could absolutely use some help. I don’t think any of us want to see the types of tryouts we saw at first base in 2023 again. As long as Bellinger is okay moving to first base eventually, this should be a fit.

The other potential hold up is surely in the gap between the MLB Trade Rumors estimate above and the more conservative contracts The Athletic and FanGraphs predicted. There isn’t a huge difference in the AAV of those deals. They range from $22 million a year to $25 million a year, but a 12-year commitment to a 28-year old with 2+ really questionable seasons since an MVP is something to balk at, especially someone as cautious as Jed Hoyer.

Matt Chapman
MLB Trade Rumors: six years, $150 million
The Athletic: six years, $127 million
FanGraphs: five years, $120 million

Matt Chapman is one of the best defensive third basemen in baseball who also hits the ball harder than anyone in baseball as you can see from this Statcast profile:

Matt Chapman Player Profile

Curiously, that ability to hit the ball hard hasn’t quite translated to being one of the best hitters in baseball. Don’t get me wrong, a third baseman who hits .240/.330/.424 with a wRC+ of 110 would be an improvement over what the Cubs got out of the hot corner offensively in 2024. However, it would also block the most likely everyday position for Christopher Morel, who may be able to improve his defense with more practice and time at third base or may demonstrate his defense is a liability.

There’s also some question mark’s about Chapman’s offensive ability ticking downward in 2023, you can see it pretty clearly in this 15-game rolling wOBA chart from FanGraphs:

15-game rolling wOBA

Rhys Hoskins
MLB Trade Rumors: two years, $36 million
The Athletic: one year, $12 million
FanGraphs: three years, $45 million

On its face a short-term high AAV deal with Hoskins to re-establish his value after recovering from ACL surgery seems like exactly the type of deal Jed Hoyer loves. Hoskins, however, is a bat-first first baseman who they Cubs would likely only sign if they couldn’t come to terms with Bellinger. In 2022 Hoskins had -6 outs above average at first base. That’s not all that different from the -5 outs above average Cubs fans witnessed from the rotating cast of first basemen who got a shot at the job last year. Bellinger had zero outs above average at first base, for what it’s worth.

But, the drop off between Bellinger to Hoskins isn’t just the defense. 2023 Bellinger was a much better hitter than 2022 Hoskins as you can see below:

Bellinger & Hoskins comparison

2023 Bellinger 130 556 26 95 97 20 7.19% 15.65% .218 .319 .307 .356 .525 .370 .331 134 26.3 -4.1 4.1
2022 Hoskins 156 672 30 81 79 2 10.71% 25.15% .216 .292 .246 .332 .462 .345 .338 122 14.1 -15.0 2.3
2022 Bellinger 144 550 19 70 68 14 6.91% 27.27% .179 .255 .210 .265 .389 .284 .278 83 -6.1 4.6 1.8
Key stats FanGraphs

For the above table I included 2023 Bellinger and 2022 Bellinger because I imagine the Cubs are keeping Bellinger’s nadir in mind as they try and make this decision. When he is good, Bellinger is undoubtedly a tier or two above Hoskins, however, when he was struggling offensively the only reason you’d want Bellinger at first over Hoskins is defense.

The bottom line is that any decision on Hoskins seems to be contingent on resolving the impasse on Bellinger. Re-read the Boras discussion above, do not pass go, do not collect a first baseman.

Jordan Montgomery
MLB Trade Rumors: six years, $150 million
The Athletic: five years, $127 million
FanGraphs: five years, $140 million

Jordan Montgomery is a very Cubs type of pitcher. He throws a lot of innings, doesn’t strike out a lot of guys, doesn’t walk a lot of guys but just gets the job done sporting an ERA that has outperformed his FIP each of the last two seasons.

Jordan Montgomery Player Profile

A deal with Montgomery would probably look a lot like the contract the Cubs signed Jon Lester to in the 2014 offseason. Both pitchers were 31 at the start of their first season after free agency, both had already demonstrated dominance in the postseason and an ability to pitch in big markets. The big difference between the two is that Lester was a much better pitcher for more years than Montgomery at the time he hit free agency. Lester had pitched all or part of nine seasons, including six seasons where he threw more than 200 innings. Montgomery has pitched all or part of seven seasons. He’s never thrown 200 innings and has only topped 150 innings four times in his career.

I can understand being reluctant to give the largest pitching contract in Cubs free agent history to a guy with a much shorter track record than Jon Lester. However, markets move, and if Hoyer and company want to add an impact starter they are going to need to face the reality of inflation.


Look, I get it. Jed Hoyer is cautious. The term I associate with him more than just about anything this side of “it’s not a rebuild”™ is “intelligent spending”™.

But it’s not intelligent to be in the bottom third of the league in terms of the largest contracts in franchise history when you are one of the five crown jewel franchises in the league. If the team can ask fans to pay the highest MLB experience price in baseball, they can certainly reconsider their contract offers to free agents. The alternative is not pretty — just ask the San Francisco Giants, who keep trying to entice players to their team with big contracts, but just can’t seem to get the deal done.