Chicago Cubs have two clear paths forward in the coming offseason

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Chicago Cubs / Jed Hoyer

(Photo by David Banks/Getty Images)

After the Chicago Cubs dropped the front end of Friday’s twin bill at Wrigley Field, the team dropped to 67-86 on the year with just over a week left to play. Of course, the postseason will follow – and the rival St. Louis Cardinals, winners of now 13 straight games, will have their eye on their third championship since 2006.

As the Cubs watch from home, missing out on the postseason for just the second time since 2015,  team president of baseball operations Jed Hoyer will begin charting the path forward for his organization. Last winter, his first at the helm following the abrupt departure of Theo Epstein, Hoyer was financially handcuffed – trading his staff ace and moving on from a pair of longtime fan favorites in Jon Lester and Kyle Schwarber in an effort to dramatically cut payroll.

This time around, though, he’ll have a lot more to work with. The team slashed and burned its way through the trade deadline, decimating the core that brought a World Series to Wrigleyville a half decade ago. In the process, they freed up tens of millions of dollars – and with just a handful of guaranteed deals on the books moving forward, Hoyer might actually get to work through the winter without one hand tied behind his back.

What he’ll do with this newfound financial freedom remains to be seen. But here’s how I think it could go, at least with where things stand right now.

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