Self deprecating, perhaps?
Or maybe he is really a "hater" of the O's, and prefers subtle humor to the more crass t-shirts like "Orioles Suck"
And there would be those who don't get the joke.
Most of you who know me on this board know I hate the Chicago Cubs with a passion usually reserved for the vilest of criminals. Sue me, that's the way it is.
But back in 2003, with the Cubs winning the NLCS 3 games to 1, a local T-shirt vendor had thousands of shirts prepared to sell for the inevitable celebration of the Cubs winning the pennant. They were your typical "Cubs 2003 National League Champions" type T-shirts. Not cheap either. Good quality print job.
When the Cubs lost the next 3 games to Florida, this guy called me, knowing I was associated with a re-sale store that supported a charity I am involved with. He said "they're worthless. Can I donate them to the re-sale shop?" WE said sure, and he took a writeoff for the cost of producing them. Our store sold them for 25 cents a piece. I bought a dozen, and they were the hit of the Christmas season in my White Sox crazed, Cubs hating family. I keep one behind the door in my office, just to pimp my Cubs fans friends every now and then.
But the funny thing is, the locals who frequented our re-sale store who were Cubs fans wore the shirts proudly, and continue to do so to this day. when I wear mine, they are shocked. "I thought you hated the Cubs?" they ask. I say I do, and its why I wear the shirt. They don't get it.
Its typical of a Cubs fan, I suppose. But I would think wearing a shirt that celebrates your team's failure and not realizing it is the height of numb-nutziness.