Chicago Cubs: These free agent targets make most sense for team this winter

Chicago Cubs found a weapon in Jon Jay

This one is more difficult. I think Jon Jay proved himself in just about every way imaginable in his first season with the Cubs. I also think not bringing him back could prove to be one of those moves that comes around to bite you.

Again, MLBTR has Jay getting a two-year deal in the $14 million range. I think that’s a fair deal for a guy who not only mentored the young guys like Albert Almora this year, but put together some of the most professional at-bats I’ve ever seen on a daily basis.

Jay posted a career-high .374 on-base percentage with Chicago this year, batting just under .300 on the year. For Joe Maddon, the outfielder became his go-to guy off the bench late in games when the Cubs needed a quality AB.

"“It’s almost a problem he’s created for himself by being so good off the bench,” Maddon told the Chicago Tribune. “It’s hard. When he starts the game you’re looking for him in the latter part of the game to plug him in in the right spot. He’s so good at that.”"

Lots of moving pieces in the outfield

Now, we have to address the elephant in the room. If Jay returns to Chicago, he’ll likely face a similar role in 2018. Almora figures to finally get a shot at the center field job on a daily basis. Jason Heyward is entrenched in right field and Kyle Schwarber, left. The Cubs also feature guys like Ben Zobrist and Ian Happ, both of whom play the outfield on a fairly regular basis.

If the Cubs bring back Jon Jay, it means someone else is gone. It doesn’t make sense to have all these pieces on the position-player side of things with the apparent pitching shortcomings. But if someone like Happ heads out of town in a trade, Jon Jay may be the perfect fit to provide Chicago further outfield depth.