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When you are trailing for a World Series and your rotation’s holding on with duct tape, every passing second matters. That is exactly where the Cubs find themselves presently. With key arms already sidelined and workloads rising, the pressure is mounting to reinforce the staff, fast. And one name, Paul Skenes’ teammate, is making the most cacophony. He is not just available; he might be the beating lifeline Chicago’s rotation desperately requires.

And the star is Mitch Keller. Boog Sciambi, the TV voice of the Cubs, did not sugarcoat the urgency while speaking on Nothing Personal with David Samson. “You’ve still got 75 games left… and they need a dude. They don’t have a ton of pitching depth,” Sciambi warned. “They’ve sustained Steele for the year, Imanaga for 45 days… I don’t think they could sustain something else again.” His concern did not stop there. “If you’re trying to win the World Series… you need a dude up front and some depth to shore up in case somebody were to go down.

Now, add Mitch Keller. Sporting a 3.90 ERA and under team control through 2028, Keller could slide in as a reliable No. 3 starter behind Imanaga and Boyd, who himself has not thrown over 80 innings since 2019. The Cubs need more than just a first-aid kit. They require a workhorse with playoff upside, and Keller perfectly fits that mold. He has already demonstrated his ability to hold his own against elite lineups and has postseason potential written all over him.

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However, the stakes are steep. Mitch Keller will not come cheap. The Pirates are thought to ask for a prospect-rich return and the Cubs will need to decide if this is the moment to cash in some of their farm depth. As per trade projections, a package engaging No. 4 prospect Kevin Alcantara and No. 16 Pedro Ramirez could get it done. 

For the Cubs, it is a balancing act between urgency and caution. However, one thing is crystal clear: waiting around could cost the team a shot at October glory. With the pitching depth already paper-thin, Mitch Keller could not just be an option; the star could be the distinctiveness between a deep postseason run or another year of ‘what-ifs.’

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However, as if the rotation was not already on shaky ground, another blow just made things messier for the Cubs—one that has pushed the urgency meter through the roof.

Cubs rotation hit again as Jameson Taillon goes down with ultimate injury

Just when things were beginning to settle, the Cubs’ pitching staff took yet another gut punch and this time engaging with veteran right-hander Jameson Taillon. On July 4, while the team was lighting up fireworks at the plate with a record-setting eight homers in a blowout win over the Cardinals, the vibe dimmed with a declaration from Craig Counsell. Taillon, who had been battling inconsistencies, faced a strained calf at a bullpen session and is now expected to miss over a month.

The timing could not be any worse. Taillon’s June was not pretty; he posted a 5.57 ERA over six starts and gave up seven homers, but his veteran presence was still important to a rotation that has been anything but stable. Counsell’s update now leaves the Cubs relying on makeshift arms as they try to patch together innings. And while Taillon’s time on the injured list might allow for a personal reset, the broader implications for a postseason-hungry team are undeniable.

One silver lining? Chris Flexen. The reliever has been lights-out this year with a sparkling 0.62 ERA in 29 innings, and he is expected to step into Taillon’s spot. The Cubs hope his starting transition mirrors his team’s dominance. But let’s be honest, banking on a reliever to carry a starter’s load is a huge gamble. It only further magnified the front office’s need to follow through on their trade deadline promise and add a frontline arm to the bullpen.

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Jed Hoyer has already indicated that the Cubs will make a splash before the deadline, and now the pressure is red-hot. Between Steele’s season-ending loss, Imanaga’s recent comeback, and Taillon’s setback, the Cubs’ playoff dreams hinge on aggressive moves. Flexen’s magic might hold briefly, but without immediate reinforcements such as Mitch Keller-type additions, this rotation could unravel faster than anticipated. Time is ticking, and the Cubs know it very well.

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