The Cubs Weren’t Able To Extend Their Young Stars Last Winter, But They’ll Try, Try Again

The Theo-Epstein-led Chicago Cubs front office is a fairly tight-knit group. In other words, rarely do their strategic plans get unintentionally revealed to the public – which is, quite frankly, a quality not all front offices around baseball can claim.

But there are a few things about an important strategic direction that we do believe we know:

1. They have a roster loaded with young, un-extended position players,
2. They’d love to extend several of them before they start hitting arbitration, and
3. They tried (and failed) to do just that last offseason.

Now that we’re on the doorstep of the 2017-2018 offseason, those conversations figure to heat back up, and the Cubs could actually get something done. Of course, as noted, the Cubs had the same incentives and motivations last year, and were not able to execute any extensions during the offseason – so nothing is guaranteed this time around.

Fortunately, Epstein doesn’t seem to be too worried, no matter what happens right now: “It would be nice,” Epstein said of wrapping up deals with young players to CBS Chicago. “I don’t think it is essential if it doesn’t happen.” Epstein went to add that talking about those efforts is not something he’s going to do in the media.

While failing again to extend some of those players certainly wouldn’t be the end of the world, I have to imagine Epstein is downplaying the desire to get something done this winter, for cost certainty and future planning purposes, if for no other reason.

Consider, first, the timing of arbitration for the following players:

This Winter: Addison Russell, Kris Bryant (Super Two), Kyle Hendricks
2019: Javy Baez, Kyle Schwarber
2020: Willson Contreras, Albert Almora
2021: Ian Happ (could always be a year earlier, depending on Super Two status)

While it’s objectively good to have so many awesome and young pre-arb players, the short time frame in which they all made their debuts (and the degree of their talent) could make payroll costs skyrocket rapidly, especially if their results continue to improve as they develop.

Second, consider the free agent class of both this and next offseason, and how involved the Cubs figure to be in both. Although the actual monetary cost may not be as big of a concern as it was under previous administrations, the newly minted penalties for exceeding the luxury tax threshold are far more severe (and include baseball operations penalties).

In other words, it would behoove the Cubs to have as much cost certainty (even if it’s not necessarily cost savings) as possible before the checks start flying around to guys like Bryce Harper (or whomever). And that starts with locking down pre-arb extensions for these younger players.

So while Epstein may be right to say it’s not “essential” to lock these guys down, it’d certainly be a beneficial outcome (and, in any case, he specifically mentioned that he would be re-engaging soon).

As for which players the Cubs can most realistically extend, there’s a lot that goes into those decisions (some deeply personal to the player, about which it’s awfully hard to speculate). But I will point a general rule that often holds true: the high-draft pick players/big-time IFA signings who received big bonuses tend to be less “desperate” to make something work, as they’ve already locked down at least some significant money in their careers. For the Cubs, that includes Javy Baez (9th overall, 2011), Albert Almora (6th overall, 2012), Addison Russell (11th overall, 2012), Kris Bryant (2nd overall, 2013), Kyle Schwarber (4th overall, 2014), and Ian Happ (9th overall, 2015).

Meanwhile, Kyle Hendricks was drafted by the Rangers in the 8th round back in 2011 and signed for just $125K, while Willson Contreras was signed by the Cubs in 2009 as an international free agent out of Venezuela for $850,000. Those are not insignificant sums, but they are not necessarily the same as generational, life-changing money that can come with an extension.

I can’t say for certain the Cubs will focus on those two, in particular, or get anything done at all, but this is definitely something we’ll be following closely this winter, so I wanted to tee it back up. And there it is.