BALTIMORE -- The Orioles enter the 2018 season at a crossroads.
On one hand, the club is in win-now mode, with the expiring contracts of executive vice president of baseball operations Dan Duquette, manager Buck Showalter, infielder Manny Machado, outfielder Adam Jones and relievers Zach Britton and Brad Brach. But most of this winter's headlines have revolved around the O's listening to offers on Machado, and there haven't been any moves to add to a rotation that has just two projected starters in Dylan Bundy and Kevin Gausman.
Teams that are aiming to win this season are retooling their rosters and committing large amounts of money to free agents. Teams that aren't are seeking out players who will be free agents soon. And this is where things get tricky.
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At last year's non-waiver Trade Deadline, the O's did not sell, which was surprising to most. Instead, they bought -- adding pitcher Jeremy Hellickson and infielder Timothy Beckham (who will shift over from shortstop to third base to accommodate Machado's position change). At least publicly, the theory was that Baltimore just needed some better pitching performances and could make a run at the postseason. (Rumors later surfaced that it nearly traded Britton to the World Series-champion Astros.)

Instead, the Orioles didn't do well in September, finishing last in the American League East and perhaps costing themselves an opportunity in July to bring back some top prospects. After all, their Minor League system has slowly improved. For the first time in a while, the O's had three prospects on MLB Pipeline's Top 100 Prospects List. They have young players, like Austin Hays and Chance Sisco that they feel good about and a lineup that's nearly intact from a year ago.
But if the Orioles are going to compete this season -- and all signs point to that being their goal -- they have to add some impact rotation pieces. Given what the Yankees have done and the Red Sox's threatening roster, the O's -- along with the Blue Jays and Rays -- find themselves in a precarious position. If they traded off all of their pending free agents, the next competitive Baltimore team would probably come together long after Duquette and Showalter were at their respective posts.

So the Orioles almost have to try to give it one more go with this group with the shrinking window and hope for the best. Should Bundy and Gausman take a step forward, they could survive. But the three other rotation question marks loom large, as does the Achilles injury that will have Britton out likely for the first half of the season.
Should the Orioles falter out of the gate, would Duquette go forward with a midseason fire sale? Or would the O's play out the stretch in what is expected to Machado's final season in a Baltimore uniform? Regardless of how the team fares, this will be a fascinating season that could very well change the direction of the organization for the next few years.