Crasnick wrote an excellent column on the O's.  Check it out here: http://sports.espn.go.com/mlb/columns/story?columnist=crasnick_jerry&id=2587235.

Choice quotes.

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The Orioles also have a knack for overrating their talent and thinking they're closer to contention than they really are. And since they can't compete with New York and Boston for top-tier free agents, they often wind up overpaying for second-tier talent. Even when the Orioles signed Tejada to a six-year, $72 million deal three years ago, the principal competition came from Seattle and Detroit.

Two American League executives, speaking on the condition of anonymity, characterized the Orioles as a team in a perpetual identity crisis. They're resistant to a full-scale rebuild like Cleveland's Mark Shapiro did in 2002, and they're not equipped to slug it out with the AL East powers.

"They've constantly straddled this line of, 'Let's see how many games we can win this year, and we'll deal with next year next year,' " said an AL general manager. "That doesn't work. You have to have a longer-term vision and approach, or you're going to be constantly chasing your tail."
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Absolutely perfect.

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The Orioles recently had two chances to reshape the team, but missed out by pushing too hard. Before the July 31 non-waiver deadline, Duquette and executive VP Mike Flanagan were close to a trade that would have sent Tejada to Anaheim for pitcher Ervin Santana and shortstop Erick Aybar. But when the Orioles asked for a third player -- Casey Kotchman was one name prominently mentioned -- Angels GM Bill Stoneman had enough time to rethink the deal and take a pass.

Another proposed deal would have sent Tejada to Houston for Roy Oswalt, Morgan Ensberg and Adam Everett. But when the Orioles wanted pitching prospect Jason Hirsh instead of Everett, the Astros said no. Houston also got cold feet when word spread that Baltimore might flip Oswalt to Texas.
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I can understand critiquing the Angels deal but screw the Astros deal.  That deal would have sent the O's backward especially since Oswalt would have been a free agent after next season.