The letter raises questions about the political ethics of a sitting mayor advocating special treatment for their family members.

“She is probably very aware of the fact that she has more power as mayor than she did before,” says Jessica Levinson, professor at Loyola Law School and past president of the Los Angeles Ethics Commission. “It doesn’t mean it’s improper to ask [for the commutation], but it does mean she should be very circumspect that she has a position of power. Every elected official only has so much political capital.”

Levinson says there was information that was not included in Breed’s letter that should have been, such as the fact that Breed was her brother’s alibi and testified on his behalf and that Brown was found with heroin in his possession while in prison.

“I think it’s her duty to provide all the pertinent facts,” says Levinson.

Breed says a lot of African-American men from her San Francisco neighborhood, the Western Addition, are in prison and negatively impacted by the criminal justice system.

“My story is not unique,” she says. “Unfortunately, it's the story of so many people who grew up in my neighborhood and other parts of San Francisco — stories that you don't always hear.”

The letter stresses the importance of rehabilitation and restorative justice, and Breed says it is consistent with her stated positions on criminal justice reform.

“Trying to provide opportunities for folks in communities like the one that my brother and I grew up with has been my life's work. It is something that I stand by,” she says. “Part of the letter was focused on the need for rehabilitation and getting the help and the support that he needs to be a productive member of society.”

She says she has written many commutation letters over the years.

Brown has issued more than 1,200 pardons and commutations in his last two terms — far more than his recent predecessors. His office has declined to comment on ongoing commutation requests.

Levinson says it's important to be critical of elected officials asking for special favors.

"I don’t think it’s the type of thing that brings democracy down,” she says. “But [Breed] is using her title and her office to try to get a favor for a family member. Hopefully, she would treat all constituents who she thought were deserving of that request the same way.”