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Jeff Cohen, owner of the legendary Horseshoe Tavern and Lee’s Palace, isn’t used to waking up early.

Yet, on more than 14 occasions over the last year-and-a-half, he has trudged, bleary-eyed, to the courthouse at Old City Hall to fight the city’s insistence on ticketing his music venues for illegal posters he says they never put up.

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He is 7-0, all victories. The remaining seven tickets, each for $490, will be heard in May and June.

“I decided a long time ago that this is crazy,” said Mr. Cohen. “It is a waste of my time and at some particular point I am going to be looking to get remunerated for the time they have wasted.”

Mr. Cohen believes that when city inspectors see a poster, instead of trying to track down the band featured on it, they fine the venue that is listed on the material. The first time he even sees the poster his club is alleged to have put up is in the courtroom, where he unleashes “one of my best Law and Order imitations” to an audience of cab drivers on hand for their own legal battles. “There is no evidence that any of my venues put up the posters or profited by putting it up or had anything to do with it,” said Mr. Cohen.