Winning Week Makes Decision to Buy Much Easier

The Cubs still haven’t made any firm decisions on whether to buy or sell at the deadline, and they may still be at a crossroads when the calendar flips to August. A lot of it depends on the offers they get because no matter what happens over the next six games, they aren’t going to move players like Cody Bellinger and Marcus Stroman just for fear of getting a comp pick or nothing in return after the season.

That said, a very successful road trip should see Jed Hoyer as the one making calls to see about adding a little power and some bullpen depth for what should at least be a competitive two-month stretch. Entering their two-game series on the South Side, the Cubs sit 48-51 and trail the Brewers by seven games. They are 5.5 games back of the Reds, who have two more in Milwaukee and then head to Los Angeles for three against the Dodgers before coming to Wrigley.

Let’s say the Cubs go 4-2 against the White Sox and Cardinals to put them at 52-53. The Reds could drop four of their next 5, getting the Cubs to within three games of them ahead of their three-game set. Catching the Brewers will obviously be a tougher task, but the Crew has to take on the Braves in Atlanta for three once they’re done with Cincy. The Cubs have by far the easiest upcoming schedule and could get right back in the hunt.

I mean, think about what happens if they really get hot and go 5-1 or 6-0 here. Those results would put them at either 54-51 or 53-52, which are absolutely buy-side records. So is 52-53, for that matter. Don’t agree? The 2021 Braves were 44-45 at the All-Star break, putting them in third place at 4.5 games behind the Mets when they traded for Joc Pederson.

The Braves had moved up to second place by July 31, but they were two games under at 52-54 and were five games out of the division lead. It’s entirely conceivable for the Cubs to have a better record and a better position within the division than the eventual World Series champs from two years ago. But it’s not at all a matter of setting up a World Series-or-bust run and thinking that’s what buying means would be a mistake.

While the Cubs can absolutely hang with anyone in the postseason based on the strength of the top of their rotation, the front office knows they have to win in a meaningful way next year. Selling at the deadline doesn’t make that any easier unless Hoyer perfectly threads the needle, something that hasn’t happened yet in his tenure. Nor is buying big in free agency anything close to a sure thing. Wanna count on prospects to carry the load on the jump to relevance? Good luck.

The best way to vault back into the conversation would be to make a few trades here that improve the roster for the rest of the season, then promote some future contributors and spend on impact free agents this winter. The key difference between selling and buying, then, comes down largely to what kind of return you’re seeking. Well, that and not shipping Stroman and Bellinger off.

The focus over the last couple of seasons has been to get back primarily young prospects who still needed several years of development. This time around, Hoyer needs to target current MLB players who can step right in and fill gaps on the roster (like power, especially from the left side, and middle relief) to set up a run and lay a foundation for the winter.

Now, this may all look a lot different if the Cubs soil the bed and drop their next six games to wind up nine games under. That ain’t happening, though. Right?