Cubs fans sit and watch as Padres work on extension with Fernando Tatis Jr.

The Cubs sell off the core while the Padres look to extend Fernando Tatis Jr.

The Chicago Cubs spent years developing a homegrown core under Theo Epstein – only to fail to extend a single member of that core. The San Diego Padres aren’t making the same mistake, as the club is reportedly working on a long-term extension with superstar Fernando Tatis Jr.

Now, that Cubs core did culminate in a long-anticipated World Series championship back in 2016. But what has the team truly accomplished since then? They’ve been competitive, sure, but since 2017 haven’t been seen as legitimate contenders come October – meanwhile, failing to lock up any of their key players for the long haul.

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Already this offseason, the club parted ways with a pair of former first-rounders in Albert Almora and Kyle Schwarber. The loss of the latter looks worse than ever after he inked a $10 million deal with the Nationals this weekend – well above what he was projected to earn in arbitration. Meanwhile, Chicago continues to actively shop two of their key players in Kris Bryant and Willson Contreras – even after cutting north of $70 million in payroll already this offseason.

Out on the west coast, the San Diego Padres are stepping on the throats of teams like the Cubs. After going out and landing Yu Darvish and Blake Snell within 24 hours, the Friars are now reportedly working on a long-term extension with their 22-year-old phenom.

Update: According to Bob Nightengale of USA Today, the two sides are yet to actually sit down begin negotiations but are expected to begin talks next month ahead of spring training.

What kind of world do we live in when the Padres are out here flexing their financial muscle while the Cubs cower meekly in the corner, mumbling incoherently about losses of ‘biblical proportions’?

The lengthy rebuild Chicago underwent in the first half of the 2010s, as I said, changed everything for the team. Being a .500 club is flat-out no longer acceptable to fans or members of the organization (although one has to wonder where the bar is set for ownership) – and when we finally get to set foot in the Friendly Confines in a post-COVID world, we’ll always have that World Series championship banner flying high above the bleachers in center field.

But how did it come to this? The window for the Cubs has been clear for the better part of a decade now. Theo Epstein and Jed Hoyer knew exactly when their core would hit the open market and it goes without saying that the primary way of keeping that window open would be inking at least a couple of these core guys to long-term extensions.

That is yet to happen.

I’d wager to say there’s a 20% chance both Bryant and Contreras are on the roster at the trade deadline this summer. The team has shown pretty much no interest in keeping Bryant’s projected $18.6 million salary on the books and Contreras is, at this point, the club’s most valuable trade chip – one that could be used to rebuild a farm system that’s pretty mediocre and features few high-impact talents.

If, somehow, the 2021 season comes and goes and not a single member of the once-coveted Chicago Cubs core is extended, I think we all have to stop and ask ourselves, “Just how did we get to this point?”