Riding the league’s hottest streak, Chicago faces a crucial slate of opponents to prove they are legitimate buyers ahead of the 2026 trade deadline.
How the Chicago Cubs perform over the next month will determine how aggressive the front office is at the trade deadline.
The Cubs currently own the top Wild Card spot in the National League with a 50-40 record. They have a 4 ½ game lead over the Pittsburgh Pirates (46-45) for a Wild Card spot and are still trying to catch the Milwaukee Brewers in the division race. Chicago currently sits six games behind Milwaukee for first place in the NL Central standings.
The North Siders are in a good spot as of now. They own a postseason spot and have been playing really good baseball over the last few weeks. The Cubs have the best record since June 11 (16-6).
This recent winning streak puts them in an ideal spot to acquire a top starting pitcher at this year’s trade deadline. Chicago has already done their “homework” on Tarik Skubal, could be in the running for Freddy Peralta, and could have their eyes set on controllable pitchers like Joe Ryan and Logan Webb.
Which one of those pitchers the Cubs ultimately go after will depend on how well they perform from now until the August 3rd trade deadline.
Luckily, the team has an extremely favorable schedule over the next four weeks. Chicago will play four series against teams under .500 and three series against teams over .500 before the trade deadline.
This stretch will begin on Tuesday against the Baltimore Orioles. The Orioles are 42-49 entering this series and are just 14-17 since the beginning of June. The North Siders won the series at home against Baltimore last season.
The Cubs will then close out the first half by traveling to Cincinnati to take on the Reds for a three-game series. The Reds are 41-48 at this point in the season and have an 11-20 record since June 1.
Following the All-Star break, the Cubs will host two sub-.500 teams. They have a three-game series against the Minnesota Twins (44-47) and another three-game series against the Detroit Tigers (40-50) at Wrigley Field.
Although the schedule does get a bit tougher toward the end of the month, it’s nothing the Cubs can’t handle. They will play three games against the Pittsburgh Pirates (46-45), four games against the St. Louis Cardinals (47-40), and three games against the Yankees (49-40) without Aaron Judge.
This 22-game stretch until August 3 is extremely important for the Cubs.
If they win 14+ games during this stretch, there is a strong chance the front office will be really aggressive at the trade deadline. However, if they only win seven or eight games, the front office might not look to acquire any pieces.
It’s definitely go time for the Cubs right now to force the front office’s hand to trade for a top starting pitcher and potentially more bullpen help.
