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Will Jemal be able to hold on to this building? (Lydia DePillis)

City beautiful types already had enough reason to growl at downtown real estate tycoon Douglas Jemal earlier this week, with a post by vacant property watchdog Cary Silverman chronicling the history of a decrepit mansion at 11th and K Northwest—it’s covered by a series of wrap ads that make the eyesore even more glaring. Turns out the District has capped the number of “special sign” permits at 32, many of them along New York Avenue NE. Billboard permits in this city are like liquor licenses under a moratorium: Each one is more valuable because there can only be so many.

Then, this morning Michael Neibauer reports that Jemal owes the city $6 million in back taxes on 79 properties—the biggest debtor on a massive list of buildings that will be sold at auction next month unless they pay up (among them is the Wonder Bread Factory, which Douglas Development has been saying might turn into a boutique hotel). Jemal sounds contrite. “I’m short of dollars, like everybody else,” Jemal said. “This is the stuff I’m carrying that I couldn’t develop.”

This led me to wonder: How many of Jemal’s properties are also recieving the benefit of those special sign permits? Out of 32, I can identify six that affirmatively belong to a Jemal-identified LLC (they’re creatively named: Jemal’s Hookers LLC, Jemal’s Britches LLC, Jemal’s Gang of 3 LLC, etc.). He’s in arrears on all of them, and the most on 111 Massachussets NW: A whopping $1.075 million in property taxes, plus another $579,223 in public space taxes. That’s pretty rough, Doug!

Of course, it would help if Jemal could lease some of his nice buildings. He’s found tenants for a few downtown, mostly eateries:  Carmine’s, Crumbs Bake Shop, and Amorini Panini are all in Douglas buildings. But many of his lovely spaces—like 1155 F Street, which is local preservation maven Tersh Boasberg‘s favorite historic renovation—are still unfilled, as is the high-profile corner spot in the Adams Morgan Harris Teeter. The list of empty windows (a few of which Prince of Petworth took pictures of and wondered about!) is looong.

The Atlantic building, sadly empty. (Lydia DePillis)

A local commercial broker tells me that Jemal is very selective with his tenants, looking for the right businesses to go into each spot. That’s certainly appreciated. But at the point where you’re not paying your bills to the city, shouldn’t you take what you can get? And if you’re not, should the city still allow you to reap the benefits of a significant chunk of the absolutely limited D.C. billboard market? Seems like it would make sense for Jemal to slim down his gigantic portfolio, pay his debt to society, and try to focus on a few properties to make them work.