The winter meetings are just a few short weeks away as the MLB offseason figures to kick into full swing during the annual league-wide congregation that will take place this year from Dec. 4-8 in National Harbor, Maryland.

Every offseason brings a unique crop of free agents and trade targets, but this winter in particular will be a unique one thanks to a barren starting pitching market.

For pitching-needy teams, the trade market will be the place to go, and that could give this year’s meetings a feeling similar to the July trade deadline when teams are wheeling and dealing.

So as teams weigh their options ahead over the coming weeks, they will have some tough decisions to make and some risky propositions to consider.

That’s what we’ll focus on here: one risky move that each MLB team should consider making.

In many cases, it’s potentially trading a key player, going back to the idea that the trade market will be busier than in most years. Other decisions include targeting a free agent, addressing an extension candidate and potentially clearing a path for a top prospect.

We’ve laid out the potential benefits of making each move, as well as why it’s a risk.

So with that, let’s begin.

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