The Chicago Cubs will likely be doing all they can to acquire a premier starting pitcher and multiple top bullpen arms at this year’s trade deadline. 

Both the rotation and bullpen remain a huge question mark heading into the stretch run. The Cubs don’t have an ace that they can go to in big games, and the bullpen has the ninth-highest ERA (4.93) since the beginning of June. The front office must fix both issues before the August 3rd trade deadline. 

The good news for that front office is that two premier pitchers could be available at the deadline. Detroit Tigers starting pitcher Tarik Skubal and San Diego Padres closer Mason Miller are both being brought up in trade rumors with 12 days to go until the deadline. 

Getting Skubal or Miller would obviously be a big-time get for the Cubs. The Tigers left-hander is a back-to-back American League Cy Young winner, while the hard-throwing Miller has become the best closer in the game.  

But it might not be realistic for the Cubs to acquire either pitcher if they are actually moved at the deadline in less than two weeks. Chicago’s front office might not be able to match the asking prices for those two All-Star pitchers. 

It remains to be seen if the Tigers will actually move Skubal at the deadline. They sit five games back in the American League Wild Card standings and have to leapfrog five teams in order to take over the final Wild Card spot. With the southpaw being a free agent at the end of the 2026 season, it is possible that Detroit moves him. 

However, the asking price for Skubal is extremely high. Ken Rosenthal reported that the Tigers are seeking a controllable starting pitcher in exchange for two months of the left-hander. Some of the names that Rosenthal mentioned were Emmet Sheehan of the Dodgers, Logan Henderson of the Brewers, Ian Seymour of the Rays, and Will Warren of the Yankees. 

The Cubs just don’t have pitchers of that caliber in their organization. The only three pitchers who fit this criteria are Cade Horton, Ben Brown, and Jaxon Wiggins. But Chicago definitely isn’t trading Horton, Brown isn't going to be moved, and Wiggins could be off Detroit's radar since he is a huge question mark. 

The Padres made a splash at last year’s trade deadline to acquire Miller. San Diego sent four prospects in return, which included sending the No. 3 overall prospect in baseball in Leo De Vries to the Athletics. 

Now one year later, the Padres might be looking to trade away the 27-year-old flamethrower. Miller has a 0.86 ERA, 25 saves, and a 48.8% strikeout rate. If he is available for trade, he would be a highly coveted closer for contending teams. 

Nevertheless, the Cubs might not be able to match the Padres’ asking price for Miller. San Diego wants at least two top-100 prospects in return. That would mean a combination of Jefferson Rojas, Josiah Hartshorn, Wiggins, or even Pedro Ramirez, who recently graduated from prospect status. 

Not only would the Cubs be hesitant to part with two of those prospects, but there's a chance it wouldn't even be enough to land Miller. The Padres are likely seeking higher-ranked prospects after getting rid of De Vries last year. Chicago’s top prospect right now is Rojas (No. 63).