“Can you please make sure your folks do not put up any more political ads? This is not good at all.”

Earlier this month, some 70 London Breed for Mayor ads popped up across the city, on bus and train shelters. They were eye-catching billboards: The candidate sported a blue blazer against a gold background and flashed a winning smile. But they were eye-catching for another reason, too: The San Francisco Municipal Transportation Agency has a crystal-clear and unambiguous prohibition against political ads being placed on transit shelters or vehicles, and a candidate poster is about as unambiguously political as you can get.

E-mails obtained by Mission Local reveal that Muni officials were caught off-guard by the ads, and were highly displeased.

“These need to be removed immediately,” Gail Stein, who manages Muni’s transit shelter and advertising programs, wrote in a one-line email to a bevy of higher-ups at both Muni and Clear Channel, a vendor responsible for vetting and placing Muni’s outdoor ads. Muni Chief Financial Officer Sonali Bose chimed in via a subsequent e-mail. “Why did these go up in the first place?? Not good.”

Bruce Qualls, Clear Channel’s vice president of real estate and government affairs, fell on his sword and took responsibility for the affair. “Our mistake,” he wrote. “Although our charting restrictions clearly state ‘no political on SF shelters,’ this somehow slipped through by human error. We have a couple new people and clear limits, but it was missed.”

Breed’s campaign consultant, Maggie Muir, told Mission Local that she worked out the ad buy with a Clear Channel representative in a discussion she says was initiated by Clear Channel. “They came and said ‘we have these for advertising. Would you like to advertise on them?’”

That political ads are verboten on Muni property is well known in San Francisco political circles. But Muir says she was unaware of this. And, in fact, she’d worked with Clear Channel only a few months before to place ads for Supervisor Jeff Sheehy on bus shelters — and, until the Breed ads popped up, nobody saw fit to complain about them.

“Apparently there is also an ad at Diamond and Bosworth for Jeff Sheehy,” Bose wrote to Qualls on March 13. “That has to come down as well. Can you please make sure your folks do not put up any more political ads? This is not good at all.”

Muir says Clear Channel has refunded the Breed campaign for its botched and abortive ad placements.

The situation left local politicos shaking their heads. “We know, straight up, that you can’t do campaign ads on bus stations. It’s that simple,” says a longtime city consultant. “You don’t have to overthink it. I don’t know what that campaign was thinking.”

Adds another veteran consultant, “It’s an oversight on the part of the consultant. But it’s a massive screw-up on the part of the company.”

Jim Ross, a longtime consultant who ran Gavin Newsom’s 2003 mayoral campaign and is still active throughout the Bay Area, said this incident left him dumbfounded. “In my experience, the review that Clear Channel puts into anything that has even the slightest amount of political context is extraordinary,” he said. “It’s shocking it would slip through due to human error.”

He added that he’s “kind of angry about this,” because “of the hurdles they’ve made our firm jump through.”

In 2016, Ross handled ads responding to a series of passive-aggressive Airbnb placements (also on bus shelters) in which the company patted itself on the back for belatedly paying the city’s hotel taxes. “We went around and around and around on what the content of those ads could be,” recalls Ross. “It took a month of approvals from Clear Channel to post them. It literally took a month to get those ads up; I’ve gone around and around with their legal counsel.”

Ross also handled an Oakland ad campaign by the SEIU during that city’s union negotiations, “and we had to totally re-do the ad so it wouldn’t mention the mayor. [Clear Channel] has a very rigorous approval process. It’s not like you just send them the art and they slap it up.”

In the end, however, Ross says the buck stops with Clear Channel. “I thought everybody knew in San Francisco you can’t buy political ads on bus shelters,” he says. “But, ultimately, it’s up to the vendor to tell you the rules of the road.”

Qualls admits as much. He did not return multiple calls from Mission Local. But his apology to Muni officials was unequivocal. “This was not cavalier disregard, but regrettable human error,” he wrote. “I know you are aware we have been historically careful with the sensitivity of these issues, and we apologize for this mistake.”

Bose responded to this missive with another one-line e-mail: “Given that it’s political season, you may want to send a reminder out to all your employees.”