Chicago Cubs: Future of Big Three hangs on results in May

CHICAGO, ILLINOIS - APRIL 04: Kris Bryant (17) of the Chicago Cubs smiles with Javier Baez (9) of the Chicago Cubs during the game against the Pittsburgh Pirates at Wrigley Field on April 04, 2021 in Chicago, Illinois. (Photo by Nuccio DiNuzzo/Getty Images)
CHICAGO, ILLINOIS - APRIL 04: Kris Bryant (17) of the Chicago Cubs smiles with Javier Baez (9) of the Chicago Cubs during the game against the Pittsburgh Pirates at Wrigley Field on April 04, 2021 in Chicago, Illinois. (Photo by Nuccio DiNuzzo/Getty Images) /
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We knew heading into the 2021 regular season that the Chicago Cubs were set to have three critical expiring contracts at the end of the year in Kris Bryant, Javier Baez, and Anthony Rizzo. I think most expected some kind of trade with Bryant to be hashed out during the winter, but alas, he is still here.

The Cubs got off to a historically bad start offensively, but they have since rebounded in a number of categories. Entering Tuesday, the Northsiders are 16th in team batting average (.234), ninth in OPS (.722), and 18th in hits (306).

In the second month of the season, the Cubs are fourth (.265), fifth (.767), and 12th (126) in those same categories.

Where do the Chicago Cubs go from here facing three expiring contracts after the season?

According to MLB Network’s Jon Morosi, May was set to be a crucial stretch of the season whether the team would sell off the three aforementioned players.

Bryant, 29, has arguably experienced the most success this season among the three players and certainly the most personally since the 2017 season. The former NL Rookie of the Year and MVP owns a robust .301/.392/.625 slash line with 14 doubles, 10 home runs, and 25 RBI’s through the first 38 games.

The Cardinals appear to be the team to beat in the NL Central Division in the early goings. Of course, they made the big offseason splash in acquiring Nolan Arenado to boost their offense. But the Chicago Cubs are hanging in with a 20-20 record and just 2.5 games back.

The momentum could quickly turn sour with a poor finish to the month, and the Cubs have an important series against those Cardinals in St. Louis this weekend.

Purely speculating, but if the Cubs were to make it through the season with all three players, it seems like the front office would keep Rizzo and one of either Bryant or Baez. That decision could be argued at nausea all day which one to keep, but ultimately, it will come down to contract length and dollars.

“It’ll be weird if all three of those guys leave and become free agents and go somewhere else,” Jon Lester said on Monday. “It would definitely be weird seeing them in different uniforms. But, unfortunately, that’s the nature of what we do. The Cubs have a business to run and they have to do what they feel is necessary to set them up for the future, whether it be financially or the guys on the field.

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Certainly, the Cubs would love nothing more than to restock their farm system with prospects for the future. If they’re hovering in the division, they’ll have to decide whether to go for it one last time with these three players or commit to a rebuild of sorts. Keep in mind, too, that Willson Contreras will need a new contract after next season as well.