One of the things that makes baseball’s offseason the most exciting of all the major professional sports leagues is that you never know what’s going to happen.

The opportunities for players and teams alike to surprise—and disappoint—with their decision-making are more plentiful than at any other point during the year. As history has shown us, everyone involved is always up for the challenge.

Whether it be a player signing with a team that nobody thought he’d go to or a team trading away someone that it insisted was not available only a few weeks earlier, the hot-stove league never leaves us wanting more.

What’s surprised and disappointed us the most thus far, with the winter meetings looming on the horizon?

Let’s take a look.

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