Sometimes, there’s a man. Well, he’s the man for his time and place. He fits right in there. And that’s … Rod Blagojevich?
Indeed. The former Illinois governor served eight years of a 14-year federal prison term for attempting to sell Barack Obama’s senate seat after Obama was elected president in 2008.
In 2020, President Donald Trump commuted his sentence. Blagojevich is now on the personalized video platform Cameo, selling messages to presumably befuddled recipients for $100 and up. It’s unclear when this would be a good or appropriate service but … sometimes, there’s a man.
“Stephen Sherrill! It’s Rod Blagojevich, and your Uncle Mike in New York asked me to send you this message,” begins an undated video obtained by Mission Local.
In the six years he’s been a free man, Blagojevich has developed this side hustle recording individualized messages full of “personality, Chicago references, and just the right amount of political flair” for “everything from bachelor parties to new moms.”
At 69, Blagojevich’s 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.
“I 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, ‘fuckin’ golden.’ And the guy that gave it to you ‘didn’t give it up for nothing.’ I said those words before; I wish I never had, those words landed me in prison…”
Blagojevich goes on for three-and-a-half minutes, praising Trump and lashing out against the “corrupt motherfucker” George W. Bush-appointed federal prosecutors who nailed him six ways to Sunday, before realizing that he’s rambling and getting back to the point.
“Uncle 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’ll say it again, fuckin’ golden.”
The political bomb-thrower who paid for this video clearly got their money’s worth.
Blagojevich went to prison for attempting to sell a Senate seat. Meanwhile, in a Feb. 6 article in the New York Post’s California edition, unnamed former Breed lieutenants alleged that San Francisco’s termed-out mayor overtly stated she was putting Sherrill in the vacant District 2 supervisor seat to curry favor with “Uncle Mike.”
That’s the billionaire former New York City mayor Michael Bloomberg, Sherrill’s mentor and Breed’s patron.
Sherrill and Breed have both denied the allegations in the article. The ex-mayor told the Post that the accusations were “incorrect … offensive and deeply disrespectful.” At present, only unnamed former Breed staffers are making these accusations. There are not yet any wiretaps or “corrupt motherfucker” prosecutors involved.
Sherrill was appointed to Catherine Stefani’s vacant seat by outgoing Mayor Breed in December 2024.
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 protégé of Bloomberg in New York City and held a Bloomberg-funded position (Director of the Mayor’s Office of Innovation) in San Francisco City Hall.
He was, furthermore, a former Republican, like Bloomberg, who 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).
Last month’s Post article 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 Bloomberg helping her secure a job once she left office.
Unlike the Blagojevich case, there is no profane and damning recording. Both Breed and Sherrill denied the allegations.
Say what you will about the Post, but my own sources close to the former mayor have described this article as “100 percent accurate.” 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.
Within City Hall, the allegations leveled in the Post story were well known long ago. But, here’s 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’s attentive, proactive and friendly, and he follows up.
District 2 is one of San Francisco’s most affluent enclaves. When Sherrill’s 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.
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.
His D2 advice: “Have two people working full-time on getting cats out of trees.”
That’s not to say that residents in District 2 don’t have issues their district representatives must work to address — issues 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.
A hardworking person can do just fine by simply doing core constituent services.
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.
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’t have a beat cop or why the playground is looking dingy — issues that aren’t exactly under the control of a district supervisor.
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.
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 — his constituents didn’t have these needs — thereby cementing citywide political allegiances.
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.
The allegations regarding Sherrill’s appointment spurred bogus emails and fliers distributed to city residents’ inboxes and doorsteps, but did not derail his endorsement by the capital-D Democratic Party. Nor did his extremely recent history of even being a Democrat.
His only major competitor is Lori Brooke. She is, perhaps monomaniacally, fixated on neighborhood housing and development issues in the same manner that perennial New York City candidate Jimmy “The Rent Is Too Damn High” McMillan is fixated on, you know, the rent being too damn high.
Brooke is seeking to cast Sherrill as a pro-development YIMBY. He voted for the mayor’s upzoning plan. Despite that, Sherrill opposed the proposed Marina Safeway behemoth — but his attempts to stave it off failed (and, in fact, were doomed to fail).
It remains to be seen, however, if voters, even the older and more established voters you’d 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’s raison d’être issue is resonant enough to carry even District 2.
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.
“Congratulations to you on your appointment,” says Blagojevich toward the end of his stemwinder. “Congratulations to you, Stephen Sherrill, on having an uncle like Mike in New York who loves you the way he does.”
That’s 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.
As demonstrated in the Blagojevich case, an office-holder doesn’t actually have to cash in on their position to be found guilty of a crime. Even the act of discussing it can be enough.
“The crime is committed at the time you’re making those statements,” explains McGregor Scott, a partner at the law firm King and Spalding and the former two-time U.S. attorney for California’s eastern district.
That’s so even if a potential quid pro quo never comes to pass: “It’s too late. You’ve committed the crime,” Scott continues. He adds that “There is no ‘just kidding’ statute.”
Breed has strongly rejected any allegations of wrongdoing. Sherrill says he got his job because he was qualified: “The facts are straightforward. Supervisor Sherrill was appointed based on his executive experience at City Hall and a record of results,” reads a statement from his campaign.
“As Director of the Mayor’s Office of Innovation, Supervisor Sherrill and his team built ASTRID, the nation’s first integrated data system to improve San Francisco’s homelessness response, strengthening coordination and accountability across city government.
“Supervisor Sherrill has the support of Mayor Daniel Lurie, the S.F. Democratic Party, a broad labor coalition, and District 2 residents, and he is focused on delivering safer neighborhoods, cleaner streets and a city government that works.”
At the conclusion of his video, Blagojevich slows his speech to make a dramatic finish: “I hope you do a great job for the people.”
Come June, the people will render their verdict.
“He was, furthermore, a former Republican — like Bloomberg — who had worked in the George W. Bush administration”
Last I checked about 10% of SF voters are registered Republicans. I imagine that percentage is higher in D2.
So even if one Supervisor out of eleven is a (closet) Republican, that leaves the GOP under-represented in percentage terms city-wide.
In my time in SF the D2 supervisor has always been the most conservative figure on the board. And as you say, as long as he/she exhibits competence the D2 voters are sanguine about how they got the office.
Meanwhile, closer to home, the D9 seat has been used as the focal point of an extortion operation that coerces contributions from unwilling developers, Fielder had to float a subpoena to coerce the extorted payment, to direct the proceeds directly into private pockets.
At least when Daly put the squeeze on Rincon Tower, he exacted $50m to the SOMA Stabilization Fund that had the developer pay the government and the government set up a process for distributing the proceeds.
In this case, the D9 seat does not even go through the motions of ethical indirection, and simply connects up the extorted with nonprofits in their political base directly.
It does not matter if an elected leverages their seat for their own benefit or the benefit of a third party. The federal crime is depriving voters and residents of honest government service.
Why does Mission Local always give city funded Mission nonprofits all consideration in print, while larding all accountability on those who oppose the nonprofit grift?
Interesting story as usual. Sometimes truth is stranger than fiction (re: the bizarre Cameo video). Minor edit is that Blagojevich has the letter h at the end. Source: Among other things, I’m a former constituent.
Paul —
Thank you for the eyes. But I bet for another $100 he’d change it.
JE
Thank you for letting us know Joe. That Breed was corrupt was obvious, coming from the Willie “The E in email is for Evidence” Brown wing of the Democratic Machine. Still, it is nice to hear the details of how that corruption works.