Chicago Cubs have the financial power to go big in free agency this winter

With just 11 days until the July 30 trade deadline, it’s all eyes on the Chicago Cubs. Will the front office work out extensions with Anthony Rizzo and Javier Baez, the latter of whom is reportedly seeking a deal north of $200 million? Or will this be the end of an era, with an exodus of big names from the 2016 World Series championship club.

Jed Hoyer has repeatedly emphasized the fact this won’t be the lengthy, gut-wrenching rebuild from a decade ago. He’s pointed out the various differences in the two scenarios, including the organizational infrastructure, revenue streams and player development framework that exist now.

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But above all else, it’s the Cubs’ payroll situation that will allow them to turn this around on a dime. Only Kyle Hendricks, Jason Heyward and David Bote are on the books for guaranteed money in 2022 and, with a loaded free agent class looming, Chicago could flex its financial muscle in a big way.

First and foremost, we all need to understand that even if the team trades all of its big three (something I still see as pretty unlikely, although not altogether impossible), there is nothing stopping Hoyer from going out and bringing back who he wants this winter via free agency.

Remember, when Chicago acquired Aroldis Chapman in exchange for a package of talent headlined by Gleyber Torres back in ’16, Brian Chapman turned around and re-signed his closer that very offseason – and he remains in the Bronx to this day. We could see Hoyer pull something similar, restocking the prospect ranks and then bringing someone like Rizzo or Baez back into the fold come the winter.

But if Hoyer decides he’s ready to take this team in a new direction – one without the services of Baez, Rizzo or Kris Bryant – he’s got more than a few options. The shortstop class alone might be the best ever to hit the open market, headlined by guys like Carlos Correa, Corey Seager and Trevor Story.

Chicago Cubs: Jed Hoyer will have almost limitless options at his disposal

That means the Cubs will have options when assembling their 2022 roster – but one thing is for sure: either via trade in the next 11 days or in free agency, they absolutely have to shore up the starting rotation – which has been in shambles pretty much since the season started after several of the team’s one-year fliers went up in flames (I’m looking at you, Jake Arrieta).

Of course, all this is assuming Tom Ricketts is going to quit pretending like he owns the Tampa Bay Rays and actually put his money where his mouth is. That’s far from a sure thing – but if he acts like the big market owner he is, the Cubs are in a position to flip this thing over quickly by dominating the upcoming free agent class.