The Cubs’ Deadline Dilemma

The 2021 season hasn’t gone as the Cubs expected after trading away their ace and listening to offers on several other highly regarded players over the winter. Trading Yu Darvish, non-tendering Kyle Schwarber and generally avoiding any additions until some bargain pickups late in the winter, the Cubs appeared ticketed for a transition year. With Kris Bryant, Javier Baez and Anthony Rizzo set to become free agents after extension talks failed to bear fruit, a retooling of some extent appeared nigh.

Perhaps the Cubs didn’t count quite so much on the inactivity throughout the rest of the division. The Cardinals eventually added Nolan Arenado in a blockbuster trade with the Rockies, and the Brewers made some nice late moves, most notably signing Kolten Wong to a two-year pact, but the NL Central was a wasteland in terms of hot stove activity. The Reds dumped their two best relievers to trim payroll and now have MLB’s worst bullpen. The Pirates, setting out on a lengthy rebuild, obviously made little effort to improve. Even the Cardinals, beyond their acquisition of Arenado, opted not to address some spotty pitching depth.

The result was an eminently winnable division for anyone other than the rebuilding Pirates. (Sorry, Pittsburgh fans.) And with all the focus on the looming turnover in Chicago after Theo Epstein stepped away and Jed Hoyer ascended to the top baseball operations spot, it almost became easy to forget that the Cubs won the division by three games during last year’s shortened season. Subtracting Darvish and Schwarber hurt, but the Cubs added some complementary veterans to round out the roster a bit: Zach Davies, Joc Pederson, Trevor Williams, Jake Marisnick, Andrew Chafin and old friend Jake Arrieta all entered the mix. It was at the very least a competent roster in a lackluster division.

Add in varying levels of resurgences not only from Bryant, Rizzo and Baez but also from written-off closer Craig Kimbrel, and the Cubs suddenly find themselves in the thick of the division race. Bryant was playing at a near-MVP level for much of the season until a recent slide. Rizzo’s bat isn’t back to peak levels but is much improved over 2020. Ditto Baez. And Kimbrel? The right-hander is sitting on a 0.59 ERA with a 46.4 percent strikeout rate against an 8.9 percent walk rate — both the third-best single-season marks of his career. He’s played so well that the $16MM option on his contract for next season suddenly looks like a bargain.

The result is a second-place Cubs team that finds itself in a gray area with just over one month until the trade deadline. Entering the year, the predominant question regarding Bryant was: “Where will he be traded this summer?” Now, it’s shifted to: “How can they trade him when they’re only a few games out of first?”

In reality, it’s hard to envision the Cubs trading anyone if they’re this close to the front of the division. To the contrary, this team looks more like a buyer than it does one that should be expected to dangle Bryant, Baez, Rizzo, Kimbrel, Davies, Pederson, Chafin or any of its impending free agents. The front office may have envisioned the Darvish trade as a launching point for similar deals down the line — clear payroll, add some young talent to lay the groundwork for the next generation — but instead the 2021 season now has the feel of one final hurrah with the 2016 core.

The context of the division and the schedule plays an important role, too. The Cubs have dropped nine of their past thirteen games, including series losses to the Dodgers and Mets. Normally, that might’ve begun to shift the team away from potential buying status, but their Central-division competition hasn’t exactly been thriving, either (outside of the first-place Brewers).

The Cardinals have dropped eight of their past 10 games as they try to weather major rotation injuries. They were recently swept by both the Cubs and by a Reds team that put its two best relievers, Lucas Sims and Tejay Antone, on the injured list. Cincinnati has now dropped seven of ten themselves. There’s plenty of talent on both the Cardinals and the Reds, but injuries have impacted both clubs quite a bit in recent weeks.

The schedule in July will be pivotal for the division as a whole. Chicago plays three games in Milwaukee and three in Cincinnati before hosting the struggling Phillies for four and the Cardinals for three. Coming out of the break, the Cubs will play six of their first 14 games against MLB’s worst team, the Diamondbacks; the others are, again, against Cincinnati and St. Louis. It’s probably not what the front office envisioned, but given all that context it’d take a somewhat of a faceplant, primarily against a series of .500-or-worse opponents, for the Cubs to really be in position to sell.

The Darvish trade, of course, looks all the more egregious now that starting pitching is precisely what the Cubs need. Sahadev Sharma and Patrick Mooney of The Athletic took a thorough look at the Cubs’ rotation needs this morning, noting that executives around the league don’t expect them to make an aggressive, blockbuster style acquisition. The likelier focus, per Sharma and Mooney, would be on pitchers with reasonably affordable salaries and/or relatively low costs of acquisition.

Fans are never going to be excited by any report suggesting that their team’s primary targets are middle-of-the-road pitchers who can simply keep them in the game for five or maybe six innings at a time, but given where the Cubs are versus where they likely expected to be, it’s also not a huge surprise. A Darvish-caliber arm isn’t walking through that door, but someone like Merrill Kelly (D-backs), Chris Flexen (Mariners, if they sell pieces controlled beyond ’21) or Tyler Anderson (Pirates, if the Cubs don’t mind sending a prospect elsewhere in the division) are all speculative names that fit that general mold.

The next few weeks of games are going to be pivotal to most clubs around the league; there aren’t many clearly defined sellers. Even underperforming clubs like the Twins and Cardinals have so many games left against division rivals and/or rebuilding teams that they’ll probably wait to definitively commit to a course of action. But there might not be a team whose long-term outlook will be so closely tied to the fate of its July performance than the Cubs.

There are long-term implications for every team this time of year, but the Cubs have a slew of short-term veterans to market if they wish to sell — several of whom are longtime cornerstones. This could be a month in which they genuinely jumpstart an accelerated rebuild — not unlike the one the Yankees engineered in 2016 when they traded away Andrew Miller and Aroldis Chapman.

On the flip side, if the Cubs continue to exceed expectations, the pendulum would swing in the other direction, likely leaving the team with some draft compensation (via qualifying offers for Bryant, Rizzo and/or Baez). Not only would they lose the opportunity to add to a thin farm via trade — they’d perhaps further deplete the current system to make a measured push to remain in the division hunt.

A few clubs always find themselves performing something of a tightrope walk this time of year, but the Cubs are among the more prominent examples in recent memory. The clubhouse probably relishes the fact that they’ve upset the front office’s expectations to date; every group of players wants to win, after all. If they can keep it up a month longer, we’ll likely be looking at a much different deadline than most expected for the Cubs after they shipped Darvish to San Diego in exchange for Davies and a handful of lottery-ticket teenagers who might not make it to the Majors before the entire roster turns over.