As the trade deadline approaches, the Chicago Cubs find themselves in first place. With the working knowledge that this actually might be the last run together with the 2016 championship core, surely club president Theo Epstein and his brain trust will attempt to be as aggressive as possible in looking to grab a second World Series championship. That doesn’t mean they’ll be able to pull of a blockbuster or anything, with so few likely sellers, but they’ll be a team bandied about in rumors in looking to shore up any weaknesses. 

Here are the Cubs’ biggest needs, targets and trade chips before the Aug. 31 deadline.

Biggest needs

First off, the starting pitching depth could use some help. Tyler Chatwood has a back injury and we can’t be sure how well Alec Mills will hold up, not to mention that Jon Lester is 36 years old. Adbert Alzolay looked great in his spot start, but his history is inconsistent, both in performance and with injury. A depth piece who can spot start would be helpful. 

It’s not near as much a problem as the numbers indicate because things have settled down since the first week or so, but bullpen depth would also be helpful. They sure could use a lefty, too, as Kyle Ryan is completely untrustworthy at this point and he’s the lone southpaw in the bullpen at present. 

Another big bat couldn’t hurt, though simply getting the actual big bats hitting probably solves Chicago’s offensive issues. On this front, they could simply try to catch lightning in a bottle by signing Yasiel Puig. 

Finally, Albert Almora’s role is basically at this point a pinch-runner and defensive replacement. Only he rates as a below-average runner in sprint speed and he’s missed a few chances at spectacular catches. He’s been an atrocious hitter since a few months into 2018. Ian Happ in center and Kyle Schwarber in left makes for a weak defensive outfield, so they could stand to upgrade Almora. 

Possible targets

Let’s pick up where we left off above and mention Kevin Pillar as an excellent Almora replacement. He’s enough of a veteran who has bounced around to be OK with a part-time role. He’s a much better hitter. Sprint speed measurements show him as much faster than Almora and he’s a perfectly capable center fielder. 


Drew Smyly

SP •






An arm that could make sense as a possible spot starter or bullpen depth is Kevin Gausman or Drew Smyly in a reunion. 


As for bullpen pieces, they could swing big for Ken Giles. My hunch is they don’t do this unless Craig Kimbrel melts down again or they lose one of Rowan Wick or Jeremy Jeffress to injury. The best lefty target likely to be out there is Tony Watson and he’d be a great fit. 

Trade chips

The four guys who found themselves on top 100 prospects lists heading into the season were infielder Nico Hoerner, catcher Miguel Amaya, lefty starter Brailyn Marquez and outfielder Brennan Davis. Epstein emptied out the organization of high-profile prospects in trades in 2016 and 2017 and we’ve already mentioned that this might be the last ride with the veteran core. It seems unlikely to me that the system would be further depleted from the highest-profile prospects. First-round pick Ed Howard and second-round pick Burl Carraway probably have value but they can’t be traded until after a year, though they can skirt things with a player to be named later deal. Again, though, I’d bet against this. 

No, instead, mid-tier prospects seem more likely to be dealt. Such as …

Though I wouldn’t rule out a huge move like Giles, the feeling here is the Cubs improve at the margins with depth trades. Something like Pillar and Watson. 


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