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Heading into the Winter Meetings, the two teams I can’t help looking at over and over are the mystery men of the MASN market. The Orioles and Nationals are in fascinating positions. Going into the offseason, I was ready to push for Baltimore to begin a rebuild in earnest, while touting the Nationals as perhaps the non-division winner most likely to win their division in 2016. So far, though, a strange break and a few bizarre decisions have pushed the two teams toward each other, in a number of ways.

Both teams, of course, are built around a total superstar with three years of team control remaining, but the similarities between them roughly end there. The Nationals remain a deep organization, ready to plug the departures of Jordan Zimmermann, Doug Fister, Denard Span, and Ian Desmond this winter with the likes of A.J. Cole, Joe Ross, Michael Taylor, and Trea Turner, and with more talent on the horizon. The Orioles’ farm system is so thin that they dealt for Mark Trumbo (at an anticipated price tag of $9 million or so) instead of waiting to see whether they could re-sign Chris Davis. In addition to Davis, Baltimore will bid adieu to Wei-Yin Chen this winter, and six weeks ago, they looked poised to really clean up. Davis and Chen will both bring the Orioles sandwich-round picks after the first round, and they figured they would be able to claim a third after they made Matt Wieters a qualifying offer in the first week of November. There was at least some argument that they ought to have given Darren O’Day one of those, too, but they elected not to.

Funny thing, though: Wieters took their one-year, $15.8-million deal. Add that money to the contracts already on the books for Adam Jones, Ubaldo Jimenez, and J.J. Hardy, and the O’s suddenly owed a shade under $60 million to four players. Given the $34.4 million MLB Trade Rumors estimates the team will owe to the nine arbitration-eligible players to whom they tendered contracts, that leaves just $25 or $30 million between their committed payroll and the franchise-record $118 million they spent in 2015, and no fewer than 12 spots to fill.

Given those constraints (because even in the modern marketplace, it’s hard to figure Peter Angelos is going to choose this winter, coming off an 81-win season, to finally loosen his purse strings), I advocated that the O’s look to sell Adam Jones (whose contract is a phenomenally saleable asset, given the projected shape and size of the free-agent outfielder market), Chris Tillman, Zach Britton, and anyone else not named Manny Machado. It seemed to me to be in the long-term interest of the franchise to rebuild the very weak fundamentals of the club, rather than try to extend a window that has already closed.

The Orioles went the other way, of course, shelling out $31 million over four years to keep O’Day. They’re likely to have a strong bullpen again next season, but unless they get stronger in a lot of places (everywhere, basically, except third base, center field, and the middle of the rotation), they’re not a contending team in the wide view. That makes this week crucial: The only way to justify the O’Day deal, for Dan Duquette, is to put other pieces in place and show the financial muscle to improve the rest of the roster.

Meanwhile, in Washington, the problem isn’t eagerness to spend money on a marginal asset, but the reticence to spend on a very valuable one. While I’m on record with my vote of renewed confidence in Dusty Baker, the loss of Bud Black over a low-ball offer is an embarrassment likely to follow the Nationals through the balance of the offseason. That gaffe might not be as damning as it feels, of course, if it weren’t part of a creeping pattern of problematic decision-making. The Nationals didn’t make Denard Span a qualifying offer, which was uncharacteristic, if nothing else. They allowed Zimmermann to leave for Detroit without a whimper, which is fine (the writing was on the wall when they spent big to shove Max Scherzer onto the front of their crowded rotation last winter), but certainly gives one pause.

For years, Mike Rizzo has been one of baseball’s most aggressive executives. It feels like he’s far away from making the kind of impact moves I expected from him this winter. The Nationals have as much raw capital (money, depth, prospects) as any team in baseball, perhaps, but they need to leverage it a bit in order to reclaim the NL East title.

I guess that’s what has me captivated by these two teams. While I think grand gestures are a grave mistake in one case and a great idea in the other, I’m waiting for that kind of move from each team. We’ll see whether either, or both, fulfill that expectation.