Jun 5, 2026 7:45 PM
Updated Jun 5, 2026 10:39 PM

Chicago’s postseason strategy hinges on securing a first-round bye. President Jed Hoyer suggests the front office may withhold top prospects unless the sliding Cubs prove they are elite.

We are less than two months away from the August 3rd trade deadline. 

At this point in the season, it’s easy to see which teams might be buyers and sellers at the deadline. Teams like the Dodgers, Braves, Yankees, and Phillies will be looking to add pieces, while the Rockies, Giants, Royals, and Angels could be looking to sell pieces. 

There are also teams that are kind of in the middle right now. They aren’t necessarily big-time buyers or big-time sellers. How these middle teams play over the next eight weeks will determine whether they buy or sell at the trade deadline. 

The Chicago Cubs are somewhere in that middle section. While they should be buyers at the August 3rd trade deadline, it’s hard to imagine them being huge buyers if they continue to play the way they have been recently. 

The Cubs are just 6-18 over their last 24 games and currently sit 5 ½ games behind the Milwaukee Brewers for first place in the National League Central standings. There’s no way the front office would be selling the farm with the team trending in the wrong direction.

That’s essentially what President of Baseball Operations Jed Hoyer told reporters before Friday’s series opener against the San Francisco Giants. 

“Your World Series odds are probably going to be correlated to your odds of getting a bye, and getting a bye is such a big deal,” Hoyer said to a pool of reporters in Chicago. “A lot of that aggressiveness is based on that ability to get the bye.” 

This is definitely an interesting comment from Hoyer with the trade deadline less than two months away. It sounds as if whether the Cubs are fully aggressive at the deadline will depend on whether they have a shot at a bye in the postseason. 

Two teams get a bye in each league in the playoffs. The top two teams in the National League and the American League get to move past the Wild Card Round and go straight to the Divisional Series. The teams that do get the bye only need to win seven games instead of 10 to reach the World Series.  

Last year, three of the four teams that received a bye made it to the Championship Series. It’s a lot easier to make a deep postseason run when you skip the Wild Card Round.  

Given Hoyer’s comments, the Cubs will need to be in a much better position in the standings to force them to be aggressive buyers at the deadline. 

Not only are the Cubs 5 ½ games behind the Brewers in the NL Central, but they are also way behind both the Braves and Dodgers for the top two spots in the NL. The Cubs (33-30) sit nine games behind the Braves (42-21) and seven games behind the Dodgers (40-23). 

If Chicago doesn’t make up a significant amount of ground in both the NL Central standings and league standings from now until August 3rd, there’s a strong chance Hoyer chooses not to go all in. 

Comments
anonymous profile image
Powered by RoundtableBuilt on infrastructure designed for real-time media. Learn more at RTB.io.© Roundtable 2026. By using this site you agree to the Terms of Use and Privacy Policy