The Cubs are expected to be active this winter, and ESPN’s Baseball Tonight Podcast put two big names on their radar: Clay Holmes and Adrian Morejon.
On the latest episode, Chicago was projected to land Holmes on a three-year, $66 million deal and Morejon on a four-year, $84 million pact. The podcast left open the possibility that Morejon could start, but made clear that, whatever his role, he would give Craig Counsell a major arm to work with.
That flexibility is what makes Morejon such an interesting fit for Chicago. The Cubs’ need in the rotation is so obvious that spending more than $80 million on a reliever alone would be tough to justify.
But if Morejon can be stretched into a starting role and still bring that dominant stuff, the price becomes much easier to swallow. The comparison that stands out is Jameson Taillon’s four-year, $68 million deal, with Morejon’s upside described as significantly higher.
The bigger picture for the Cubs is simple: the pitching staff has to catch up to a position-player group that was elite on both sides of the ball in 2026. Injuries and underperformance wrecked the rotation and bullpen, and a year that opened with World Series hopes ended with a Wild Card whimper in San Diego. With a lockout expected in early December, the market could move fast in November, and Chicago is already being linked to some of the biggest arms available.
If Holmes and Morejon were both added and used as starters for the sake of the exercise, the Cubs’ 2027 rotation would start to take shape with Clay Holmes, Justin Steele, Adrian Morejon, Edward Cabrera and Ben Brown.
There is some depth behind that group in Braxton Garrett and Javier Assad, which helps. But there are still real questions.
Steele will be about two years removed from his last MLB start by next spring. Cabrera was a disaster in 2026 and remains a major wild-card.
Brown’s recurring neck issues are also a concern.
That’s why landing Holmes and Morejon may not be enough on its own. If Chicago checks those boxes, the next move could be bringing back David Peterson to deepen the rotation. That would give the Cubs more arm talent overall and could even open the door to moving Brown into a late-inning role, both to protect his health and to strengthen the bullpen.
In Other News...
Jed Hoyer Is Sending Cubs Fans A Familiar Offseason Warning
The Cubs offseason is already taking shape with a familiar kind of restraint. Rather than diving into the top of the pitching market, the front office is being linked to a quieter plan that reflects both budget realities and the uncertainty hanging over the sport. Tarik Skubal would be the kind of arm that changes a rotation, but Chicago appears prepared to watch from the sidelines while bigger-spending clubs like the Dodgers and Mets set the pace.
Instead, the focus seems to be on more manageable moves, including trying to bring back pitchers such as Clay Holmes and David Peterson while exploring whether Adrian Morejon could be stretched into a starting role. The broader message from the GM Meetings was less about urgency than caution, a sign the Cubs may be waiting to see how the market and the labor situation develop before making their biggest decisions. [Read more 🡒]
Cubs May Be Losing A Dream Pitching Target At The Worst Time
The next MLB offseason already has the feel of something unusual, with collective bargaining talks looming and a likely owner-implemented lockout set to begin Dec. 2. If that happens, the usual winter rhythm could get thrown off, which is why the General Managers Meetings in November may end up carrying more weight than usual for clubs trying to get business done before the calendar gets turned upside down.
For the Cubs, that matters because one of the biggest pitching names on the market may be slipping out of reach. Tarik Skubal had been viewed as a potential dream target, but reports now indicate Chicago is not expected to be among the major bidders, a notable shift for a team that could have used a front-line arm if the market opened the way many expected. With the offseason already looking volatile, the Cubs may have to watch a premium opportunity move elsewhere before the real bidding even fully begins. [Read more 🡒]
Ben Brown Uncertainty Just Raised The Stakes For Cubs Free Agency
The Cubs already had a rotation puzzle on their hands entering the offseason, with multiple free agents to sort through and injury concerns lingering around the staff. Ben Brown only adds to the uncertainty. The right-hander has not resumed throwing after a recurring neck injury, and the possibility of surgery has put another layer of doubt over how Chicago approaches its pitching plans.
For a team trying to rebuild the rotation, Browns status matters because it changes the level of risk the front office has to manage. Chicago cannot afford to treat the staff as a finished project, and the latest update only reinforces the need for aggressive moves as the Cubs weigh how much help they need and how quickly they need it. [Read more 🡒]