Chicago Cubs could go all-in with a Mookie Betts trade this offseason

If you’re looking for the Chicago Cubs to make a splash this offseason, it’s hard to envision any bigger than trading for a former MVP in Mookie Betts.

The window is two years away from slamming on the Chicago Cubs. The team will lose Kris Bryant, Anthony Rizzo and Javier Baez at the conclusion of the 2021 season, leaving what can only be called a massive void in the lineup.

Now, it stands to reason Theo Epstein will lock up at least one of these guys long-term. It’s pretty hard to envision Rizzo finishing his career anywhere other than Chicago, but, at least to this point, there’s been no substantive progress in talks with any of the three.

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So let’s work with what we know. The Cubs are coming off their most disappointing season since they shocked the baseball world, winning 97 games and making a run to the NLCS in 2015 under then-first year manager Joe Maddon, knocking out the rival Pittsburgh Pirates and St. Louis Cardinals in the process.

Expectations have shifted dramatically – and finishing above .500 is no longer the measuring stick for success at the Friendly Confines. It’s World Series-or-bust for the North Siders – and that’s the mentality they should operate under this offseason.

Mookie Betts isn’t going to sign an extension with the Boston Red Sox. He’s essentially said as much in his comments to the media. The four-time All-Star and three-time Gold Glove outfielder is going to test the free agency waters next winter – plain and simple.

NBC Sports Boston recently opined on potential landing spots for Betts – and, to no one’s surprise, the Cubs are mentioned in said column. Which absolutely gets the wheels turning when you’re thinking about what adding a player of this caliber could mean for the team in 2020.

"They’d have to get creative to fit Betts for even one year since the top 15 players on their roster will count for more than $200 million next year. Their farm system is also pretty wiped out, but don’t discount Theo Epstein, who drafted Betts in 2011 and has watched him blossom into a superstar from afar."

Betts is coming off another stellar campaign in Boston, where he slashed .295/.391/.524 in 150 games. Serving primarily as the Red Sox’ leadoff hitter, he turned in numbers that, when paired with the Cubs’ core, could come together in an otherworldly lineup.

Imagine Betts, who had a .903 OPS out of the leadoff spot this season, setting the table for the likes of Rizzo, Baez, Bryant and Kyle Schwarber. That’s one of the most potent offensive groups in all of baseball and adding him addresses perhaps the team’s two most glaring needs – a true top-of-the-order presence and a legitimate center fielder.

Pulling off a deal wouldn’t be easy – and not just because the Chicago farm system is a far cry from what it once was. Per MLB Trade Rumors, Betts is projected to pull in north of $27 million this winter in his final year of arbitration eligibility. Adding that amount to an already-record payroll seems unlikely, thus necessitating payroll-shedding moves on the Cubs’ side of things.

I’m not saying it’s impossible – but it’s hardly likely, either. Still, Epstein has pulled off some pretty incredible moves in the past and adding Mookie Betts, knowing you’re going all-in on 2020 is a bold move – and one that might help the Chicago Cubs get one more ring before embarking on their next rebuild.