Mohammed Nuru, San Francisco's director of public works, has been arrested on federal charges of honest services wire fraud and lying to the FBI.
Restauranteur Nick Bovis was also arrested on for federal charges of honest services wire fraud.
The wo men were caught plotting five different illegal schemes, according to US Attorney David Anderson.
Nuru steered a contract for new homeless shelters and public toilets designed in the style of the Victorian Painted Ladies to Lefty O'Doul's owner Nick Bovis, said Anderson. The two were also plotting airport contract bribery and kickbacks, Anderson claimed.
Both defendants appeared in federal court Tuesday afternoon. Nuru's attorney said he looks forward to addressing the charges in court. A lawyer for Bovis declined comment.
The two men were released on a $2 million bond.
On Twitter, Nuru calls himself Mr. Clean SF, and posts regular messages about his work in city government.
He's been visible during efforts to improve conditions in homeless encampments with regular visits from cleaning crews.
In a biography on the public works department website, Nuru also highlighted his involvement in the design of the city's Navigation Centers.
He worked in city government during Ed Lee and Gavin Newsom mayoral administrations too.