However, it is clear that reinforcements are needed. President of baseball operations Jed Hoyer knows this. He’s also in the final season of his contract, so any moves he could try and pull before the upcoming MLB trade deadline could directly affect his future. Of course, if Hoyer decides to stay pat like he has in the past, then another opportunity for Chicago to capture a World Series title could certainly pass them by.
One area that needs help is the starting rotation. Imanaga is back, but left-hander Justin Steele is out for the foreseeable future due to Tommy John surgery. Veteran Jameson Taillon is also on the shelf, and Javier Assad is still dealing with a strained oblique. It’s safe to say that Imanaga, Matthew Boyd and prized rookie Cade Horton need help. There is one arm that Hoyer and the Cubs’ brass should target. That arm is none other than Pittsburgh Pirates veteran Mitch Keller, who is in the midst of a career season. What type of package would it take to bring Keller to Wrigley Field?
Mitch Keller could provide big boost to Cubs rotation

The trade market for starting pitching does look a bit thin heading into the deadline. The top arm is likely Miami Marlins ace Sandy Alcantara, even with his inflated ERA in addition to his ups and downs. Although Alcantara is under contract for the next couple of seasons, there’s no telling if he will ever return to his previous Cy Young form. That is why an arm like Keller, who has long been a dependable option, might be worth a bit more in this season’s market.
The current Pittsburgh rotation staple is under contract for the next four seasons, so it would give the Cubs plenty of time to see if this career year he’s currently having is sustainable. The good news is that Hoyer and his front office still has a solid farm system. There are plenty of options that the Pirates would love to have. For example, a package centered around one of their Triple-A outfielders in Owen Caissie or Kevin Alcantara, plus a young pitcher who has shown flashes in the majors, like Jordan Wicks or Ben Brown, would be a good start to offer Pittsburgh.
It would likely take a little more than that to get Keller in the door, particularly before this year’s trade deadline. One or two more pieces, particularly younger names such as MLB.com top 30 ranked Jaxon Wiggins (ranked eighth, in Double-A) and infielder Ben Cowles (number 22, in Triple-A as well), could be enough for Hoyer to bring Keller to Wrigley Field. If that type of deal does go down, then the Cubs’ chances at another World Series run should increase considerably.