I'm not sympathetic to people in this position, which of course has nothing to do with logic. He's relying on the old strategy: Better to ask for forgiveness than permission. Every time that works, it erodes the belief that the rules apply to everyone.
“The village is interested in compliance. . . . The rules apply to everybody. They apply them equally,” said Suellen Ferguson, an attorney who represents Chevy Chase Village in the case. Ferguson said the swing set initially was described as an “arbor” in documents his family submitted requesting a variance. Then, things got a little wild. Time went on, swings started being attached... It became a play structure.”