World Series gives Cubs fans a glimpse of what might have been

Cubs fans can't help but wonder what might have been with this World Series. (Photo by Tom Pennington/Getty Images)
Cubs fans can't help but wonder what might have been with this World Series. (Photo by Tom Pennington/Getty Images) /

The Dodgers and Rays provide two different maps the Cubs could follow.

This year’s World Series features a pair of model franchises. On one hand, you have the low-budget Tampa Bay Rays who are consistently competitive and annually one of the most talented teams in the league, despite one of the lowest payrolls in the game. On the other, you have the Los Angeles Dodgers, run by former Rays GM Andrew Friedman – armed with small market innovation and a large market budget. Meanwhile, the Chicago Cubs are stuck somewhere in the middle.

When you look at this year’s Fall Classic matchup, it really puts the Cubs’ current situation in perspective. They should have the resources of a team like the Dodgers, who traded for and then extended superstar outfielder Mookie Betts this spring via a record-breaking contract. But their success goes far beyond their financial strength.

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Friedman has done what many hoped Chicago would do after winning a World Series back in 2016. He’s paired big-name signings with one of the top farm systems in the game: one that keeps cranking out quality talent, including the likes of Gavin Lux, Will Smith and Walker Buehler, among others.

That’s allowed him to lead the Dodgers to the postseason with ease year-in and year-out. This year marks the eighth consecutive NL West crown for Los Angeles – and their third pennant in the last four seasons.

On the other hand, the Rays are in the World Series for the first time since 2008. They’re a small market team that relies on scouting and developing young, controllable talent – working with a payroll this season that roughly mirrored what the Dodgers paid Betts and Clayton Kershaw alone.

For years, Tampa Bay has been fantastic when it comes to developing pitching. That’s no different this year – as they’ve paired Blake Snell and Tyler Glasnow with veteran Charlie Morton, giving them a devastating trio atop their rotation.

They fleeced the Pirates in the trade that netted Glasnow and outfielder Austin Meadows. While neither ever really panned out in Pittsburgh, they’ve flourished with the Rays – a testament to the infrastructure the organization has in place down in Florida.

So what about the Cubs?

For the last few years, we heard about the spigot that Marquee Network would open up in terms of cash flow for the team. Instead, a viral pandemic crippled the team’s ability to spend – and it’s been several years since we saw the team bring up a top prospect ready to impact the game (sorry, Nico Hoerner is a far cry from a Will Smith or Walker Buehler).

The team plays in a big market and has not only national but worldwide brand recognition. But for three years now, the Cubs have tried to piece together competitive rosters, hoping to do just enough to sneak into the postseason and roll the dice.

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With Theo Epstein in his final year with the organization, it’s worth looking in the mirror and asking ourselves: is it time to reimagine what the front office looks like? Because the status quo, while it has admittedly led to a championship and several October runs, isn’t delivering what we all expected four or five years ago.