At 49-35 overall with a 2.0-game lead in the National League Central division, the Chicago Cubs appear to be in decent shape as the 2025 season enters its second half.
But there is one aspect of the record that should be a concern as the team attempts to build on its postseason aspirations. Despite all the winning and the good times at Wrigley Field, the Cubs, after losing two of three in a weekend series at Houston, are only 23-26 against teams with a winning record, while they are 26-9 against opponents at .500 or worse.
That does not bode well for a team selling its fans on a World Series run, especially given the uncertainty surrounding Kyle Tucker’s future in Chicago. Which makes it all-the-more imperative that the Cubs get it right at the trade deadline.
Cubs Tabbed as ‘Most Aggressive Possible Suitor’ for Pirates Starter Mitch Keller
There’s no mystery to what the Cubs will be targeting. The team’s rotation has been a mess since the season began.
Justin Steele was lost for the season after Tommy John surgery. Shota Imanaga is expected to return this week after missing significant time with a hamstring problem. Javier Assad suffered a late April setback in his recovery from the oblique injury that has kept him out since spring training, and the team has offered no recent update on his rehab.
As for the pitchers who have been making starts, Jameson Taillon is the only one that has consistently pitched to expectations, but he is at best a No. 3 starter, and more likely No. 4, on a team with October plans.
Matthew Boyd appears to have avoided anything major with the shoulder concern that halted his previous start. However, with a 2.65 ERA through 16 starts that is nearly two runs better than his career average, can the Cubs realistically rely on more of the same from the 34-year-old left-hander?
Colin Rea was an early season surprise out of the bullpen, boasting a sub-3.00 ERA after his first seven starts, but he has given up four earned runs or more in four of his last seven outings, suggesting the magic may have worn off. Top prospect Cade Horton has impressed in his MLB debut, but the inevitable growing pains make it difficult to rely him being a leader in the pennant race. Ben Brown has struggled in his first full season as a starter and could soon be removed from the rotation.
Injuries, underperformance, and innings limits on young arms have created a pile of concern and frustration, and fans have been clamoring for a trade. According to MLB insider Bob Nightengale of USA Today, there could be one in the works.
In the “Around the Basepaths” section of his Sunday column, Nightengale reported that the Cubs have been involved in “serious trade talks” with the Pittsburgh Pirates over starting pitcher Mitch Keller. Mark Powell of FanSided concurred, stating that the Cubs “have been the most aggressive possible suitor for Keller.”
“That’s not a great look,” Powell said of dealing with a division rival, “but still understandable if the Cubs are willing to overpay.”
Mitch Keller is 2-10 Despite a Sub-4.00 ERA for Pittsburgh
It was just 18 months ago that the Pittsburgh Pirates committed five years and $77 million to Keller, but circumstances in Pittsburgh have shifted enough that what once looked like a long-term building block could soon become valuable trade capital.
Despite boasting a pipeline rich with young arms at both the major and minor league levels, the Pirates find themselves hamstrung by a stagnant payroll — a situation only worsened by dwindling crowds and an offense that simply hasn’t kept up. Keller’s own win-loss line is telling: a dismal 2–10 record despite a sub-4.00 ERA, a reflection of an anemic lineup offering little support.
While top starter Paul Skenes and outfielder Oneil Cruz are the only players team insiders describe as off-limits, Keller’s deal — once seen as a sign of commitment — now looks like a trade chip with genuine value. Could the 2023 All-Star bring value to the Cubs rotation?
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