addison russell batting cubsAs the Cubs work their way in and out of free agency, we’re constantly thinking of their payroll flexibility. Most often, we consider payroll flexibility for additional, future free agents, but there are a couple of other ways it’s useful. Making trades for expensive players is always a possibility – like Miguel Montero – as is extending young talent that’s already in-house.

As it turns out, the Cubs have a lot of young talent they might want to extend. And while every team in baseball should be envious of the Cubs’ glut of exciting young players, they will probably become less envious eventually, given what they might cost in a few years, especially if the Cubs hope to retain them into their free agent years.

By my count, the Cubs’ young positional core includes seven players (ages in parenthesis): Anthony Rizzo (26), Jason Heyward (26), Kris Bryant (24), Jorge Soler (23), Javier Baez (23), Kyle Schwarber (22) and Addison Russell (21). If you’re having a bad day, just read that list over and over. (And maybe also check out my earlier article on how notable and impactful such a collection can be.)

Anthony Rizzo has already signed an extension that keeps him under team control through 2021, and Jason Heyward has the option of staying for plenty of money and years if he wants, as well. So, after subtracting those two, the Cubs have five young position players that they could arguably want to extend beyond their current team control, and, according to Bruce Levine, the Cubs are keeping those extensions on the mind.



If you recall, Brett took a look at each of the five possible extension candidates a few months ago, apropos of rumored Bryce Harper extension discussions. Everything he said at the time remains true, but this is something we’ll have to constantly keep in mind. Although the Cubs won’t be able to (or necessarily want to) extend each of those five position players, the looming possibility of a few extensions remains. More importantly, which/how many/for how much players are extended will have a dramatic impact on the Cubs ancillary moves in free agency and trades (expanding or limiting flexibility, depending on what the deals look like).

To be certain, none of Kris Bryant, Kyle Schwarber, Addison Russell, Javier Baez or Jorge Soler will be easy to extend. That group consists of four first round draft picks that scored some decent money and one international free agent who signed a large deal that allows him to enter arbitration, as well. Not to mention, two of the above players (Bryant and Russell) are represented by the notoriously successful agent, Scott Boras.

Let’s examine this group in a slightly different way than Brett did before, though. Let’s assume (generously) that all five remaining players perform well over the next two or three years – well enough that extending them would be desirable. Which players might make the most sense to extend from the Cubs perspective, and which might they let play out their current team control?

Kris Bryant is 24 years old (as of yesterday) and has six more years of control, pending the resolution of his service time grievanceBy the time he becomes a free agent, Bryant will be entering his age 30 season. While I feel pretty confident that he will still be a successful player at that age (and that the Cubs would love to have him for, say, ages 30-33) he might be the guy most likely to play out his years of team control and then hit free agency un-extended. Given all of the information (his agent, his age, his expected price tag, the service time stuff, and his enormous signing bonus), I’d say Kris Bryant and the Cubs might have six more (hopefully glorious) years together, and then a parting of ways might make sense for both sides. Perhaps if the Cubs were willing to consider an extremely long extension, something could be worked out, but, ultimately, I see a low probability of an extension.

Jorge Soler and Javier Baez are currently 23 years old. Soler will be a free agent after five more seasons and will be 28 years old; Baez will be a free agent after six more seasons and will be 29 years old. Soler has already made a good chunk of change (and is guaranteed much more), and Baez netted a sizable signing bonus, though he’s earned much less than Soler thus far. Given the tentatively injured past of Soler, the age of Baez at free agency (29), and Baez’s guaranteed money so far, this duo represents the “medium” probability of an extension. It could make some sense for each to want to ink a long-term deal. But, from the Cubs’ perspective, the value the Cubs would be getting by extending into the post-control years sooner rather than later might not be as worthwhile as saving the money and spending it elsewhere.



Lastly, we have Addison Russell and Kyle Schwarber. These are the youngest two players, as Russell is scheduled to hit free agency at just 27, Schwarber 28. Extending either of these two players represents the best use of money – based on number of “prime” years being gobbled up. Even if all six of these players were good from now until free agency, all six will eventually decline. All else equal, getting as many of the youngest years as possible is inherently less risky. In that regard, Russell and Schwarber might be the most likely candidates for extensions, at least from the Cubs’ perspective. Spending money on them might return the most bang for the buck.



To address the Russell/Boras connection for a moment, I may have an alternate view of how it could play out than others. As it stands, most believe that Russell will not sign an extension, because Boras will feel that the young shortstop will get more in free agency. While that might be true, I still think the Cubs stand a chance, as you have to always remember that an individual player ultimately dictates his own contractual future. Further, while Russell is uniquely young, there’s no doubt, that could cut both ways in extension talks – for example, because of that, the Cubs might be all the more confident handing out an extension that is closer in value to what he can receive in free agency. If they offer it sooner rather than later – and before his bat breaks out – it becomes all the more possible.

The biggest wrench in all of this is could be the newly-adopted trend of opt-outs in free agency. The future possibility of two prime contracts after leaving the Cubs for Russell, for example, (assuming he opts out of his first free agent deal and scores a second) might be far too valuable for the Cubs to match.*

Whatever happens, if the Cubs so choose, this core will be together for a very a long time. Keeping talent is always desirable, but just about every guy is already under control for six more seasons. The Cubs are set up for sustained success beyond that, as well, and maybe we’ll come to find that there’s a certain window for this group before a new group ushers in the next era. We’ll see how the sides proceed.

Still, these types of extension discussion typically occur after free agency dries up and Spring Training approaches (the players are often too busy during the season and the front office is often too busy after). So keep an eye out and an ear to the ground, because if any extension discussions are going to happen, they might happen soon.

*(Of course, the Cubs could offer an opt-out and/or a player option year or two in an extension, themselves, but that’s a conversation for another day.)


Keep Reading BN ...

« | »