If Cubs don’t extend Willson Contreras, this is a historic failure

The 5 PM CT trade deadline came and went – and Chicago Cubs fans furiously refreshed Twitter, waiting to see a late-breaking trade involving at least one of the team’s two All-Stars, Ian Happ and Willson Contreras.

Instead, they were met with this tweet, courtesy of Ken Rosenthal:

And, sure enough, both Happ and Contreras are in Chicago’s starting lineup Tuesday night at Busch Stadium in St. Louis, where the Cubs kick off a series against the Cardinals. After an emotional week for players and fans alike, it was a widely unexpected anticlimactic conclusion to matters, leaving the front office in a precarious position when it comes to Contreras, in particular.

The three-time All-Star will now run out the clock on the final year of his current deal, poised to hit free agency at season’s end for the first time in his career. Given the league and MLBPA were unable to agree on terms for an international draft, the qualifying offer system remains in place and looks likely to play a big role in Contreras’ foray into free agent waters this offseason.

It’s mind-blowing to me the Cubs were unable to find any deal that would prove more valuable than a compensation round pick they’d receive should they offer Contreras a qualifying offer and he declines – but that’s exactly where we are now.

Even if Contreras accepts a hypothetical qualifying offer at season’s end, then we’re left doing this exact same thing again next summer – except then the Cubs would have just two options: trade him or simply let him play the 2023 season out before, once again, hitting free agency – this time without the burden of a qualifying offer.

Cubs front office is treading on thin ice with Willson Contreras

Of course, there is a third option – one that seems to be the front office’s only way of saving face given how bungled the entire Contreras affair has been: finally sitting down at the table and hammering out a multi-year extension.

The only problem with that idea is that the Cubs have had years – literally years – to do so, but haven’t. The two sides haven’t talked about a long-term deal since 2017, the year after, as a rookie, Contreras played a key role in the team winning a World Series for the first time in 108 years.

There’s no other path forward at this point. The front office is, when it comes to fan perception and Contreras, played with the casino’s money right now. Without an extension, not trading this guy and walking away with nothing more than a high-risk lottery ticket this winter could be a mistake that ranks among the biggest in franchise history.