\u201cStephen Sherrill!<\/a> It\u2019s Rod Blagojevich, and your Uncle Mike in New York asked me to send you this message,\u201d begins an undated video obtained by Mission Local. <\/p>\n In the six years he\u2019s been a free man, Blagojevich has developed this side hustle recording\u00a0 individualized messages full of \u201cpersonality, Chicago references, and just the right amount of political flair\u201d for \u201ceverything from bachelor parties to new moms.\u201d\u00a0<\/p>\n At 69, Blagojevich\u2019s 1980s local TV anchorman haircut is now decidedly grey. He sits in a room resembling a well-apportioned 19th-century train car, in front of a bookcase full of historical nonfiction tomes.\u00a0<\/p>\n \u201cI understand you were just appointed District 2 supervisor by Mayor London Breed. Well, congratulations to you, my friend! That is a big deal. Appointments like that are, to quote me<\/a>, \u2018fuckin\u2019 golden.\u2019 And the guy that gave it to you \u2018didn\u2019t give it up for nothing<\/a>.\u2019 I said those words before; I wish I never had, those words landed me in prison\u2026\u201d\u00a0<\/p>\n Blagojevich goes on for three-and-a-half minutes, praising Trump and lashing out against the \u201ccorrupt motherfucker\u201d George W. Bush-appointed federal prosecutors who nailed him six ways to Sunday, before realizing that he\u2019s rambling and getting back to the point.\u00a0<\/p>\n \u201cUncle Mike in New York thinks the world of you. He took the trouble to get a guy like me, a former governor of Illinois, former inmate No. 40892424, to send you this message congratulating you on your appointment as District 2 supervisor in San Francisco. An appointment which is, I\u2019ll say it again, fuckin\u2019 golden.\u201d\u00a0\u00a0<\/p>\n The political bomb-thrower who paid for this video clearly got their money\u2019s worth. <\/p>\n Blagojevich went to prison for attempting to sell a Senate seat. Meanwhile, in a Feb. 6 article in the New York Post\u2019s<\/a> California edition, unnamed former Breed lieutenants alleged that San Francisco\u2019s termed-out mayor overtly stated she was putting Sherrill in the vacant District 2 supervisor seat to curry favor with \u201cUncle Mike.\u201d\u00a0<\/p>\n That\u2019s the billionaire\u00a0former New York City mayor Michael Bloomberg, Sherrill\u2019s mentor<\/a> and Breed\u2019s patron<\/a>.\u00a0<\/p>\n Sherrill and Breed have both denied the allegations in the article. The ex-mayor told the Post that the accusations were \u201cincorrect \u2026 offensive and deeply disrespectful.\u201d At present, only unnamed former Breed staffers are making these accusations. There are not yet any wiretaps or \u201ccorrupt motherfucker\u201d prosecutors involved.<\/p>\n A Cameo video recorded by disgraced former Illinois governor Rod Blagojevich for Supervisor Stephen Sherrill at the behest of \u201cUncle Mike from New York.\u201d <\/p>\n Sherrill was appointed <\/a>to Catherine Stefani\u2019s vacant seat by outgoing Mayor Breed in December 2024. <\/p>\n As Mission Local noted at the time, it was a jarring decision: Sherrill was largely unknown in the community, and had no legislative experience. He was a prot\u00e9g\u00e9 of Bloomberg in New York City and held a Bloomberg-funded position (Director of the Mayor\u2019s Office of Innovation) in San Francisco City Hall. <\/p>\n He was, furthermore, a former Republican,\u00a0like Bloomberg,\u00a0who had worked in the George W. Bush administration (Sherrill re-registered to no party preference in 2009 and only became a registered Democrat in August 2023).\u00a0<\/p>\n Last month\u2019s Post article<\/a> quoted anonymous sources close to Breed. They said that the soon-to-be ex-mayor spoke openly about how the Sherrill appointment was done expressly to improve the likelihood of\u00a0Bloomberg helping her secure a job once she left office. <\/p>\n Unlike the Blagojevich case, there is no profane and damning recording. Both Breed and Sherrill denied the allegations.\u00a0<\/p>\n Say<\/a> what you will about the Post, but my own sources close to the former mayor have described this article as \u201c100 percent accurate.\u201d The shortlist for District 2 appointees, notably, contained candidates who had legislative experience, had deep neighborhood connections and had registered as Democrats prior to 2023.<\/p>\n Within City Hall, the allegations leveled in the Post story were well known long ago. But, here\u2019s the thing: Even politicos who believe that Sherrill was appointed under dubious circumstances also say that, by and large, Sherrill is doing a fine job as supervisor. Constituents tell me the same: He\u2019s attentive, proactive and friendly, and he follows up.\u00a0<\/p>\n District 2 is one of San Francisco\u2019s most affluent enclaves. When Sherrill\u2019s constituents get their first opportunity to actually vote for him in June, it remains to be seen if D2 voters even perceive a wealthy individual using his connections to get ahead as a negative.\u00a0<\/p>\n What does it take to succeed as a District 2 supervisor? Bill Barnes served as a legislative aide to former District 2 Supervisor Michela Alioto-Pier. He was also a legislative aide in Districts 4, 6, 8 and 11, so he has some context. <\/p>\n His D2 advice: \u201cHave two people working full-time on getting cats out of trees.\u201d\u00a0<\/p>\n That\u2019s not to say that residents in District 2 don\u2019t have issues their district representatives must work to address \u2014\u00a0issues beyond cats in trees. But, blessedly, they are, for the most part, not the issues of poverty, neglect and addiction experienced by denizens in Districts 5, 6, 9 or 10. Being supervisor here is different. <\/p>\n A hardworking person\u00a0can do just fine by simply doing core constituent services.\u00a0<\/p>\n Sherrill is doing that. Constituents say Sherrill generously distributes his personal cell and returns calls and texts. That goes a long way in a place where, by and large, people are doing all right, and are often able to solve their own problems.\u00a0<\/p>\n District 2 does come with some special challenges for a supervisor. Constituents here may have outsize expectations: People who follow the rules and pay lots of taxes may wonder why they don\u2019t have a beat cop or why the playground is looking dingy \u2014\u00a0issues that aren\u2019t exactly under the control of a district supervisor. <\/p>\n City Hall officials from prior eras note that those pressures have eased since the advent of 311, which gives residents an easy-to-remember number to call whenever they see a cat in a tree.\u00a0<\/p>\n A forward-thinking District 2 supervisor can go far. When Gavin Newsom was D2 supe, he made sure to push money to nonprofits in the Tenderloin or Bayview \u2014\u00a0his constituents didn\u2019t have these needs \u2014\u00a0thereby cementing citywide political allegiances. <\/p>\n That worked out well for him. Supervisor Stefani made combating gun violence a signature issue of her stint as D2 supervisor, even though, blessedly, it is not pervasive in District 2. She is now an assemblymember.\u00a0<\/p>\n The allegations regarding Sherrill\u2019s appointment spurred bogus emails<\/a> and fliers distributed to city residents\u2019 inboxes and doorsteps, but did not derail his endorsement<\/a> by the capital-D Democratic Party. Nor did his extremely recent history of even being a Democrat.<\/p>\n His only major competitor is Lori Brooke. She is, perhaps monomaniacally, fixated on neighborhood housing<\/a> and development issues in the same manner that perennial New York City candidate Jimmy \u201cThe Rent Is Too Damn High<\/a>\u201d McMillan is fixated on, you know, the rent being too damn high.\u00a0<\/p>\n Brooke is seeking to cast Sherrill as a pro-development YIMBY. He voted for the mayor\u2019s upzoning plan<\/a>. Despite that, Sherrill opposed<\/a> the proposed Marina Safeway behemoth \u2014 but his attempts to stave it off failed (and, in fact, were doomed to fail<\/a>).\u00a0<\/p>\n It remains to be seen, however, if voters, even the older and more established voters you\u2019d expect in a June primary, are going to get worked up about this and blame Sherrill for it. It remains to be seen if Brooke\u2019s raison d\u2019\u00eatre issue is resonant enough to carry even District 2.\u00a0<\/p>\n If Sherrill wins handily in June, he may clear the field for November. And if he wins that race, it would be his final term, leaving him seeking the next step in his political ascent. Recent District 2 history indicates there may well be one.\u00a0\u00a0<\/p>\n \u201cCongratulations to you on your appointment,\u201d says Blagojevich toward the end of his stemwinder. \u201cCongratulations to you, Stephen Sherrill, on having an uncle like Mike in New York who loves you the way he does.\u201d\u00a0<\/p>\n That\u2019s a twist of the knife from the scriptwriter for former inmate No. 40892424. But, truth be told, the more proper recipient of this video from a man popped for attempting to sell a public office is not Sherrill, but Breed.\u00a0<\/p>\n As demonstrated in the Blagojevich case, an office-holder doesn\u2019t actually have to cash in on their position to be found guilty of a crime. Even the act of discussing it can be enough.\u00a0<\/p>\n \u201cThe crime is committed at the time you\u2019re making those statements,\u201d explains McGregor Scott<\/a>, a partner at the law firm King and Spalding and the former two-time U.S. attorney for California\u2019s eastern district. <\/p>\n That\u2019s so even if a potential quid pro quo never comes to pass: \u201cIt\u2019s too late. You\u2019ve committed the crime,\u201d Scott continues. He adds that \u201cThere is no \u2018just kidding\u2019 statute.\u201d\u00a0<\/p>\n![\"A](\"https:\/\/www.newsbeep.com\/us-ca\/wp-content\/uploads\/2026\/03\/edit-1breed-930x620.jpg\")
London Breed watches Daniel Lurie get sworn in on Jan. 8, 2025. Photo by Abigail Van Neely. <\/p>\n![\"\"](\"https:\/\/www.newsbeep.com\/us-ca\/wp-content\/uploads\/2026\/03\/012226_MMG_Faith-leader-fast-9-930x621.jpg\")
The United States flag flies above City Hall on Jan. 22, 2026. Photo by Mariana Garcia.<\/p>\n