Bernstein: This Cubs Convention Will Be Weird

It's difficult to figure out what the Cubs will be celebrating this weekend.

Dan Bernstein
January 15, 2020 - 1:21 pm

(670 The Score) It's hard to figure out what we're celebrating at the 2020 Cubs Convention that kicks off Friday afternoon in Chicago, and it's making for a bit of an awkward vibe.

This tradition began in simpler and more innocent times, when marketing chief John McDonough came up with the concept of a chance to come out of the winter cold and into the cozy comforts of brand nostalgia. In 1986, this meant the shared identity as lovable losers, still embraced despite a playoff appearance just two years before and personified by all of the players from the ill-fated 1969 team still available for handshakes, hugs and autographs (there were no smartphones or selfies).

It became something more over the years, growing in size and significance and adapting with a calendar seeming to flip pages faster. The convention is now the springboard into Arizona, a launch party of sorts for the season at which expectations can be set and narratives rolled out amid a structured and corporatized series of breakout sessions and sponsored fan experiences.

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When the Theo Epstein era began, the convention fomented the renewed sense of hope encouraged by the Ricketts family ownership. Even as the rebuild trudged ahead and the losses piled up, there was reasonable excitement for what was to come, looking at the high draft picks that would become prized prospects. Ownership was transparent and available, reassuring fans at every turn that the resources would be there to achieve what once seemed impossible.

Turns out it wasn't. 

The euphoria of Joe Maddon's tenure swept the convention into the tsunami of deep playoff runs and a championship, and it became part of the reveling in glory, as much rekindling the mardi gras of a generational and transformative achievement as getting anybody ready for the next campaign. And there were the owners, out among the masses to soak up the adulation.

It has all brought us to a strange and uncomfortable place.

The Cubs' title was four years ago already, now the subject of its own kind of nostalgia. The last two seasons have ended with a grim Epstein vowing renewed determination amid needed changes, after his free-agent signings keep blowing up in his face and the organization fails to develop pitchers. The Cubs hired a new and unproven manager and yet another round of new coaches, while the front office has been restaffed and reordered in an effort to better compete. Those prospects from years ago are now close enough to free agency to spur the team's desire to trade some of them, lest they pay an onerous luxury tax on total payroll. We've endured the exposure of an owner's virulently racist emails and the ugly saga of Addison Russell's spousal abuse and suspension that ultimately resulted in his dismissal.

The players from 1969 are dwindling in number, the longtime Wrigley Field organist retired, there's little clarity about whether large swaths of the metro area will be able to watch Cubs games on television and this offseason has brought no big league acquisitions to date, to this point sending the message that there's more desire to hold onto money than to try to improve their chances of winning while they can.

And there's nothing on the schedule for this weekend that says any of the owners will be around to take questions about an increasingly uncertain future.

Dan Bernstein is a co-host of 670 The Score’s Bernstein & McKnight Show in midday. You can follow him on Twitter @Dan_Bernstein.