Libby Schaaf Oakland Mayor Becomes Oakland Roots Head Cheerleader - Video When Oakland Mayor Libby Schaaf was running for Mayor of Oakland, and through her first year, some people and especially in the right-wing media would point to her time as an Oakland Skyline High School Cheerleader, and call her the City's "Head Cheerleader." Sometimes derisively and arguably with not a small bit of sexism. That written, it's hard to argue with the moniker in the specific case of yesterday's Oakland Roots Pro Soccer Block Party. To say the Mayor of Oakland let her hair down would not be an understatement. Libby got into it. Leading the crowd in an "O" cheer that would make the Oakland Raiders proud, except the team's headed to Las Vegas by 2021. Dancing and jumping up and down, and in total, just having herself a good old time! But details. It's nice to see Libby having a little fun and enjoying Oakland's newest sports organization. She did manage t