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Navigating the Chicago Cubs’ Murky Extension Waters

The Chicago Cubs enter the 2021 season finding themselves at a rather significant crossroads. How they maneuver it will be extremely telling for the future.

MLB: Chicago Cubs-Workouts Allan Henry-USA TODAY Sports

The 2020-21 offseason was another rather unfriendly one for those that call the Chicago Cubs their team of choice. While the myriad reasons for the evaporation of goodwill between the organization and its fans are fairly well-documented at this point, it was a winter that saw the departure of Theo Epstein, the trade of Yu Darvish, and another round of minuscule spending added to the list of grievances that has been piling up over the last few years.

Nonetheless, the team enters 2021 as a contender for a division title. Their counterparts in the National League Central moved at an equally glacial place, with the trade of Nolan Arenado to the St. Louis Cardinals serving as the only genuinely impactful addition to the division. As such, the Cubs are hoping that their 11th hour slight increase to the budget that paved the way for signing the likes of Joc Pederson, Trevor Williams, and Jake Arrieta, along with a handful of other fringe types, will be enough to lead them to a repeat of the 2020 NL Central standings.

However, even with the impending season very nearly upon us, there are some massively impactful conversations that will likely be had this spring as to the future fate of the “core” members of the Chicago Cubs: Kris Bryant, Anthony Rizzo, and Javier Báez. All three are set to have their contracts expire at the end of this season. Willson Contreras isn’t too far behind, either, as he’ll be eligible for free agency following the 2022 campaign. For the purpose of this conversation, though, we’ll just focus on the former three names because of that timeline.

It’s important to note that all three (four, if you include Contreras) have stated their desire to sign a long-term deal to stay in Chicago. That’s not a new thing either, as each of them have been pretty consistent in their respective desire to remain with the team into the future. The question for the Cubs is how they navigate this. Do all three get re-signed? Do two of them? Do they choose just one to make the lone face of the franchise? As jarring as it would be to see any of these three play in a uniform that doesn’t feature royal blue pinstripes, the emotions and feelings themselves aren’t going to translate into a desirable contract. The onus is on the Cubs to provide that.

The purpose of this exercise is just to examine the statistical context surrounding each player: recent output, performance trends, etc. Projecting contracts is not my arena, so I’m going to avoid that entirely in favor of trying to determine what makes each an essential signing for the Cubs and if any of the three are more essential than the others.

And that conversation starts with Kris Bryant. Bryant might represent the most interesting of the three, in terms of a long-term contract, not only for what that contract could look like, but the entire narrative around it. The team manipulated his service time, a grievance was filed, he struggled through 2020, and then was the subject of rampant trade speculation, to the point where he got a “Welcome to the Mets” text message over the course of the winter. Kris Bryant has every reason to want a fresh start somewhere, but continues to be wildly insistent that he would love to remain a Cub.

Two of the last three years have been difficult for Bryant. The 2018 season was one in which he suffered through a shoulder injury that not only cost him games but was almost assuredly negatively impacting his overall performance as he attempted to play through it. The 2020 season was Bryant’s first as a below-average offensive player going by wRC+ (77), and he had more injury issues, this time with the oblique. This has left something of a narrative surrounding Bryant labeling him as “injury prone” and not worthy of a nine-figure deal as he was earlier in his career.

However, it’s not as if Kris Bryant is that far removed from a level of play that borders on elite. In 2019, he slashed .282/.382/.521/.903. That’s far more in line with his career averages. The 2020 season should largely be considered a wash for most, especially for someone dealing with injuries and so many players likely dealing with more of a psychological burden than they may be accustomed to. When you look at Bryant, those two seasons are the outliers. There aren’t any seasons in which he looks like a “flash in the pan” type, where he can’t replicate his previous performance because it was so outlandish. Prior to his injury woes, he was one of the steadiest players in the game.

What makes Bryant so intriguing among the core three is how the Cubs choose to evaluate him. Those injury-riddled seasons, being more recent, could have a larger impact on negotiations than we might think, considering the body of work. This could lead to A. The Cubs revisiting a trade at this year’s deadline or B. A low offer that Bryant turns away and leads to his departure in free agency.

In a general sense, the Cubs appear to be better off with Bryant than without him. Without him, you’re looking at David Bote full-time. Or maybe Christopher Morel. Or, in the longer term, one of the host of shortstop prospects currently developing in the system. The free agent market is thin at the hot corner and any trade candidates are unlikely to find their way to the North Side. Of the three, Kris Bryant would seem to be the most likely to call another city home, given the history, but wouldn’t the Cubs be better-served to lock in some certainty to the position for the next few years, given their other options?

Unlike his counterpart at the other end of the infield, Anthony Rizzo has been seen as something of a lock to sign a longer term deal. There are important considerations here too, though. On the positive side, you’re getting a remarkably consistent player. Prior to 2020, four of six seasons featured at least 30 homers and the two others were 27 and 25, respectively. He reaches base at a high clip (.372 for his career). His approach is always above average, with a walk rate that regularly sits between 10-12% and a strikeout rate of 15.8% for his career. And he’s always hit lefties better than he’s been given credit for. Defensive metrics be damned, he’s had a couple of Gold Gloves along the way as well.


Rizzo will be 32 before the season is over. He’s had fairly consistent back issues over the past couple of seasons. Nothing that has hampered his performance for too long a stretch, but he’s good for it at least once or twice a year. His last contract was also a wildly team-friendly deal (seven years, $41 million). The two sides were reportedly apart in previous discussions. Aside from Rizzo, you’d likely be looking at an intriguing prospect in Alfonso Rivas as a replacement, with powerful Matt Mervis (undrafted out of Duke) in the longer term. You’re not signing Freddie Freeman in free agency, given the financial climate. The question is the same with Bryant. Why wouldn’t you go for the certainty here, considering your other options?

Shortstop is interesting because the Cubs do have some names coming up, and there are a wealth of options sure to be available via trade or free agency. But when you’ve got one of the most exciting players in baseball in Javier Báez, do you really want to go another route? I could write a novel on the intricacies of Báez, but I’ll keep it short. The 2020 season notwithstanding, Javy looks like one of the elite at the position. In 2018 and 2019, he posted wRC+ figures of 131 and 114, respectively. He hit 64 home runs between the two. He managed to ever-so-slightly cut down on his strikeout rate, before video left the dugout in 2020. He’s shown an increased tendency to drive the ball to the opposite field (27.9% in 2019). His defense is exceptional (save the occasionally erratic arm), as is his baserunning.

With Javier Báez, you’re taking him on with his flaws. You could find someone better at the position, but at what cost? Probably one more than the organization is willing to spend. And when you consider the intangibles that Rizzo brings, Báez brings some of his own, with a significant impact on the international signing side. Again, something that’s difficult to quantify, but amplifies his value to this organization all the same.

Ultimately, it’s an uncomplicated situation that gets all the more complicated on paper. If you’re a Cubs fan, you likely want all three back. If you’re the Cubs, you likely want all three back (at the right price). If you’re one of the three, you want to be back. And we know that the Cubs can fit all three onto the payroll. Their individual flaws notwithstanding, the organization is probably better off with each of these guys on their infield than without them.

It’s worth wondering, though, if they’d be comfortable shelling out those three contracts at once or if timing could inhibit their willingness to sign all three. If so, who do you sign? On paper, you could probably afford to let Rizzo walk. But why would you, when you consider the stability and the intangible things he brings? There’d be rebellion. Same with Báez. What about the consistency of Kris Bryant, when he isn’t battling through shoulder and oblique issues? Why would you let that walk or, worse yet, intentionally trade it?

One would imagine that the spring will lend some clarity to the situation, and most often players want these situations resolved before the regular season starts. But as simple as the idea of signing three of your core players is, the context and intricacies surrounding each makes these waters far more difficult to navigate as the Cubs set off into the fog of 2021.

Randy Holt is a contributing writer for Beyond the Box Score. You can follow him on Twitter @RandallPnkFloyd.