Crossing the Line: Can the Cubs and Cardinals Match on a Trade?

One of the more interesting aspects of this rivalry, especially over recent years, is the number of players who have moved directly from one franchise to the other. While trades between the two teams almost never occur (key word: almost), free agents have found homes in both St. Louis and Chicago recently, including Dexter Fowler and Willson Contreras leaving the Cubs and Jason Heyward joining them (just in time to give the most expensive speech in sports history). 

But could this year be the year that the two teams finally align in terms of need, surplus, and value? The Cardinals are really, truly sellers for the first time in forever, having shipped off Jordan Hicks to Toronto and Jordan Montgomery to Texas over the weekend. And the Cubs are at least prospective buyers, riding their recent eight-game winning streak to an over .500 record and in the hunt for the divisional lead and one of the three wild card slots. 

The Cubs’ needs are relatively obvious this year: a first baseman, starting pitching depth, a reliever (especially a left-handed one), and (depending on your feelings on Nick Madrigal) a third baseman. The Cardinals, as aforementioned, have already begun shipping off pitchers. What remains in their cupboard on that end is Jack Flaherty (a rental SP having a solid back-end of the rotation season), Giovanny Gallegos (a righty reliever with a few years of team control remaining), Ryan Helsley (a fireballing closer who was an All-Star last year) and Steven Matz (a lefty starter who pitches exceptionally well against the Cubs and not-so-great against the rest of the league). 

On the positional side, Paul DeJong is heavily rumored to be available and can play all over the infield. Brendon Donovan may also be floated, though his price tag will be exorbitant even before the rivalry tax is applied. And while Nolan Arenado and Paul Goldschmidt fit the Cubs’ roster like a glove, there is no conceivable world where the Cardinals would willingly hand one of their two MVP-caliber players over to the Cubs. 

So the question this all begs: given that the Cubs are (likely) buying and the Cardinals are certainly selling, could the two franchises move past their rivalry to reach an agreement on a mutually beneficial trade? Would you want to see the Cubs fork even a single prospect over to the Cardinals, knowing they’ll likely apply their voodoo Cardinals magic to turn them into the next Lou Brock? Or perhaps you’re content just to watch the fireworks, hoping the Cubs make smart moves elsewhere while the Cardinals blow up the foundation of their team? 

No matter how you see it, this deadline is sure to provide some sort of spectacle, even if the Cubs are less involved than in years past. And with a little bit of persuasion from Jed Hoyer and crew, the Cubs and Cardinals can make a trade that leaves the rest of the MLB stunned.