Theo Epstein Still Trying to ‘Thread the Needle’ for Second Straight Offseason

Have you ever had a pair of pants or a shirt that you loved too much to let go despite literally coming apart at the seams? Or maybe you grew up with limited means and had to wear hand-me-downs. Either way, you know what Theo Epstein and Jed Hoyer are dealing with as they work with a presumably tighter budget to squeeze one more season out of a roster that appears to be wearing thin.

That means pulling out the old sewing kit and getting to work with a few patches. Hey, you never know, maybe the requisite tailoring will actually end up making the team look better while still setting the organization up for continued success.

“We have to be honest about our performance,” Epstein said during his end-of-season presser. “Is it possible to thread the needle and improve in 2021, while also setting ourselves up for the long-term future? I think it is.”

If that sounds familiar, it’s because Epstein said nearly the exact same thing back in January. The Cubs really started showing that money was a concern following the 2018 season, then they started talking more openly about a tighter baseball budget last year.

That’s when we heard about serving multiple masters: being competitive now, staying competitive in the future, and maintaining financial flexibility.

“This is one of those winters where it’s really hard to thread the needle,” Epstein explained during Cubs Convention last January. “We’re doing the best we can. I would say to hang with us, and hopefully by the time Opening Day rolls around, we’ve improved the 2020 team, [or] we’ve done some things that maybe don’t improve the ’20 team but ensure a better future.”

The Cubs did improve over 2019, at least in the sense that they actually earned a very brief postseason appearance. However, the painfully apparent offensive anemia that’s plagued the team for three years and the failure to extend or trade any core players means they really just kicked the can down the road on that whole “better future” thing.

Now we’ve got the president of baseball operations repeating himself almost verbatim, but with a much less desirable set of circumstances providing the backdrop for his words. Like Epstein, four of the Cubs’ core players are under contract for just one more season. What’s more, all four of them — Anthony Rizzo, Kyle Schwarber, Kris Bryant, and Javy Báez — are coming off of career-worst campaigns that could significantly hamper their trade value.

Of course, that’s only if the Cubs finally look to make any such deals in the first place. The likelihood of dealing from what was once viewed as their strength might actually be lower than ever, simply because the respective returns could be too low to be worthwhile. At the same time, the potential to extend any or all of the players in question may be much greater as the result of their 2020 results and the economic uncertainty the pandemic has created.

As Jordan Bastian laid out for Cubs.com recently, Rizzo and Báez “still look like the best bets for an extension” at this point. Javy himself had said during spring training that talks between the two sides were progressing before the COVID shutdown halted them. Rizzo made a few waves during the winter when he and his camp expressed displeasure with the lack of progress in their own conversations, but the first baseman has been the team’s de facto captain for several years and the Cubs surely want to keep that going.

Kris Bryant, whose story more than a few fans still misunderstand despite all the publicity it’s received, has long been discussed as a potential trade chip and may still be. But with an arbitration salary of at least $20 million for a lone year of control and a third consecutive season hampered by injury, there’s ample reason to believe the Cubs would be executing little more than a salary dump by moving him.

Even though Scott Boras, Bryant’s agent, isn’t known for negotiating smaller deals, it’s possible something could be worked out that keeps the former MVP on the North Side while also reducing his impact on payroll. Bryant would get additional security and would get to keep playing alongside his friends while the Cubs can get some of the financial flexibility they so desperately covet.

Schwarber is perhaps the most likely to be moved simply because he is the most easily replaced and might have the most relative value in a trade. Though his defense in left field has improved over the years, his hit tool simply hasn’t developed like the Cubs believed it would and his power has to be near elite to offset it. That said, he’s only in line for something like a $10 million payday and he can still mash.

To truly thread the needle means setting the Cubs up to win in 2021 and beyond without spending much, though exactly how the “beyond” part works is what the front office really needs to determine. Do they run it back with the same core, knowing that some of them will walk after next season? That might seem like an odd strategy, but resetting the tax penalties heading into a new CBA while also seeing those rookie deals fall off and presumably getting Marquee into the black in a big way means the budget should swell. Should being the operative word.

The other option would be to move a couple of those increasing salaries this winter for whatever they bring back in return, then using some of the surplus to sign KBO star Ha-Seong Kim. Primarily a shortstop, the 25-year-old has played third base and can likely handle some other spots as well. He’s got a 70 arm, 60 speed, and he has walked more than he’s struck out over the last two seasons.

Regardless of what they do in terms of bringing players into the organization, the Cubs absolutely must get bigger contributions from players already in the system. They need to make good on the promise to be more aggressive with pitching development, perhaps by getting Burl Carraway and Michael Rucker into the bullpen mix for ’21. It can’t stop there, though, as the prospect pipeline has to supply talent to replace what will inevitably be lost to attrition across all areas of the roster.

Now we wait to see whether and how Epstein is able to thread the needle, then we have to hope the results aren’t just sew-sew.