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This Trade Deadline Could Break Up The Cubs’ Almost-Dynasty

Back on June 13, around when I wrote about the MLB contenders that should consider adding players for the stretch run and playoffs, the Chicago Cubs appeared to be positioned very well within that category. They were 38-27 on the year, tied for the third-best record in the National League and boasted a 63 percent playoff probability. That made their Doyle Number — a measure of how much a team should consider buying extra talent for a World Series run — the eighth-highest in baseball, at 1.16. (Meaning wins added in pursuit of a title this year were worth giving up a little extra in the future.) With a handful of star players still around from the core that won the 2016 championship, there remained a feeling that the Cubs could compete for another ring in 2021, if not beyond.

But all of that has changed in a hurry. Since that day in mid-June, Chicago has gone into a full tailspin, losing 19 of its past 25 games. Its record has dipped below .500, into a tie for ninth in the NL, and its playoff odds are down to just 9 percent. As a result, the Cubs’ Doyle Number is now 0.11, meaning any talent they add this year at the expense of the future would almost certainly be wasted in a futile bid at the postseason.

And the team seems to know it, too. "When you're in this moment and your playoff odds get into single digits, at this time of the year, you have to keep one eye on the future," team president Jed Hoyer said last week. "You would be irresponsible not to take [trade offer] phone calls and think through them.”

The Cubs are in a particularly interesting place when it comes to trade-deadline decision-making because so many of their stars are set to be free agents after the season. According to’s wins above replacement, 10 of Chicago’s 16 best players this year are either free agents or have contract options next offseason, with big names on the move potentially including Javier Báez, Kris Bryant, Anthony Rizzo and Craig Kimbrel.1 The recent losing skid could result in a radically different Cubs roster by season’s end than the team was originally thinking about carrying into October. (Indeed, Chicago already kicked off the sale on Thursday by dealing outfielder Joc Pederson to the Atlanta Braves.)

Many of the Cubs’ best players are not set to return

Current salary and future contract status for Chicago Cubs players with at least 0.5 wins above replacement in the 2021 season

Player Pos Age WAR Current Salary 2022 Contract Status
Javier Báez SS 28 2.5 $11,600,000 Free agent
Willson Contreras C 29 2.5 $6,650,000 Arbitration
Craig Kimbrel P 33 2.0 $16,000,000 Club option
Kris Bryant OF 29 1.9 $19,500,000 Free agent
Andrew Chafin P 31 1.6 $2,250,000 Mutual option
Patrick Wisdom 3B 29 1.4 $570,500 Pre-arbitration
Keegan Thompson P 26 1.3 $570,500 Free agent
Nico Hoerner 2B 24 1.2 $570,500 Pre-arbitration
Kyle Hendricks P 31 1.0 $14,000,000 Under contract
Anthony Rizzo 1B 31 1.0 $16,500,000 Free agent
Matt Duffy 3B 30 0.8 $1,000,000 Free agent
Dan Winkler P 31 0.8 $900,000 Free agent
Zach Davies P 28 0.7 $8,630,000 Free agent
Jason Heyward RF 31 0.7 $21,000,000 Under contract
Brad Wieck P 29 0.7 $570,500 Pre-arbitration
Ryan Tepera P 33 0.6 $800,000 Free agent
Dillon Maples P 29 0.5 $570,500 Pre-arbitration

Players without a salary listed at were assigned the 2021 MLB minimum of $570,500.


If they were to be shipped off, the departures of Bryant, Rizzo and/or Báez would be particularly significant for the Cubs franchise. They are three of just six players on Chicago’s 2021 roster left over from the 2016 team that ended the team’s 107-season championship drought, along with Jason Heyward, Kyle Hendricks and Willson Contreras.2 And their importance goes deeper than that. By WAR, Bryant and Rizzo were the two most valuable players on that 2016 team during the regular season (Báez ranked ninth on the star-studded roster). The trio starred in the postseason, too: Báez won co-MVP honors3 for his .318 batting average and .833 OPS against the Dodgers in the NLCS, while Bryant and Rizzo combined for a .941 OPS during the Cubs’ entire playoff run -- and that pair even teamed up to record the final out of Chicago’s dramatic Game 7 victory.

Losing any or all of those three players could be seen as a distinct turning point for the Cubs’ post-World Series era -- a period that had started with the promise of potentially building into a dynasty, given how much talent Chicago had on hand. The fact that it never happened is one of the big head-scratchers of the past decade: How was a team with baseball’s top rotation and one of its best and youngest collections of position-player talent, plus an all-star brain trust and a consistently top-10 payroll, able to win only four total postseason games and one series in the half-decade that followed?

In truth, the 2016 core wasn’t together and playing at the height of its powers for very long. Most of the same roster returned -- but regressed -- in 2017, and then a slightly overhauled Cubs team showcased the cruel abruptness of the wild-card game in 2018. After missing the playoffs in a disappointing 2019 campaign, Chicago had a resurgent regular season in 2020 but quickly crashed out of the postseason. Along the way, the team said goodbye to manager Joe Maddon and team architect Theo Epstein, to go with an ever-growing list of players from 2016 who have departed in the intervening years.

While there remains some chance that the group of former Cubs won’t expand to include Báez, Rizzo and Bryant over the next few weeks, the team finds itself at a crossroads it wasn’t necessarily expecting to roll up to just a month earlier. "Eleven days ago, we were fully on the buy side of this transaction and everyone was calling about that," Hoyer told reporters last week. "Obviously, people are now calling to see which players are available, so it's a very different scenario than we expected.”

"Life comes at you fast.”

Check out our latest MLB predictions.

CORRECTION (July 17, 2021, 11 a.m.): A previous version of the table in this article incorrectly listed several Cubs players as free agents after the 2021 season. Patrick Wisdom, Nico Hoerner, Brad Wieck and Dillon Maples are not yet eligible for arbitration.

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  1. The Cubs have a club option on Kimbrel, so they could bring him back if they wanted. But he’s also one of the more attractive relief options on the deadline trade market, so it would probably be wise to deal him while his value is high.

  2. Jake Arrieta is also a member of both the 2016 and 2021 Cubs, but he played three seasons in Philadelphia in the intervening years.

  3. With pitcher Jon Lester.

Neil Paine was the acting sports editor at FiveThirtyEight.