All 30 MLB Teams' Biggest Potential Roadblock to a Successful Offseason

We've spent a lot of time the past few weeks identifying areas of need for each MLB team this coming offseason and establishing potential targets to address those needs both in free agency and on the trade market.

However, as you're well-aware, things don't always go according to plan when it comes to a team's offseason approach.

If it did, Jon Lester probably would have wound up signing with the Chicago Cubs, Boston Red Sox and San Francisco Giants last winter.

So with that in mind, let's take a look at the biggest potential roadblock standing between each MLB team and what could be considered a successful offseason.

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