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Recently, in a letter to DDOT from his attorney, Mr. Gray said he had submitted all the necessary paperwork and considered the issue “resolved.”

“This is not true,” said Lamont Regester, chief inspector at DDOT, adding that an application may have been filed erroneously with DCRA.

But Michael Rupert, a spokesman for DCRA, said his agency does not have a completed application either.

DDOT wrote letters on March 4, March 26 and April 9 threatening to fine Mr. Gray, but it has not acted.

“This is a courtesy reminder that you must submit a complete public-space permit application no later than Monday, April 12,” Karina Ricks, associate DDOT director, wrote to Mr. Gray on Friday. “Failure [to do so] will require DDOT to commence enforcement via fines on Tuesday, April 13.”

Mr. Nickles said he was “troubled” by the inconsistent enforcement efforts by DDOT and DCRA.

“I’m no permits expert, but I do understand plain English,” he said. “The letters clearly state that fines will be issued.

“It’s bizarre,” he added. “I’m unhappy with the performance of our agencies.”