It’s 2011, and a star-studded group of people — from will.i.am to Yahoo CEO Marissa Mayer — stand on a roof with a sprawling view of San Francisco behind them, ready to perform some hip-hop moves at the behest of millionaire tech mogul Ron Conway. The celebrities are wearing bright orange T-shirts that read “Fear the Mustache” as they gyrate in a video promoting Conway’s preferred mayoral candidate, Ed Lee.

The premise of the video was offbeat for a campaign ad — a remake of MC Hammer’s “2 Legit 2 Quit” — but if Conway asked you to show up, you showed up.

The video found a wide audience, and Lee was elected several months later. Over the next six years, Lee would position himself as an advocate for tech companies in the city, with Conway often close behind and cheering him on.

In an effort to blend the worlds of tech and politics, the two weren’t shy about making public appearances together. As their association grew, so did the perception that San Francisco politicians, too, would dance on demand for Conway.

As San Francisco finds itself in the midst of an unexpected mayoral campaign after Lee’s death, accusations are flying about Conway’s influence in a battle between moderate and progressive candidates.

At the same time, his role in Silicon Valley — the source of his power and authority in San Francisco politics — is diminishing. His venture fund, now mostly run by his son, shrank after a bitter split with a partner. Some of his allies — such as Mayer, who left Yahoo last year after its sale to Verizon — have faded from the tech scene.

Conway insists that he’s become too busy to meddle in local politics.

“I agree that the mayor’s race in San Francisco is important, but there are national issues right now that superseded that, and I’m spending all of my time on those issues,” he said.

Yet under the dome of City Hall, talk of Conway’s influence lingers.

Raised in the Bay Area, Conway has been a major tech investor and political donor for years. Just as he’s known to throw hundreds of thousands of dollars to moderate and tech-friendly candidates, he has also funneled money into hundreds of startups, including early investments in Google, Dropbox and Airbnb.

He has many philanthropic endeavors, like the San Francisco Citizens Initiative for Technology and Innovation, which represents tech companies in the Bay Area. He was an early backer of Sandy Hook Promise, the anti-gun-violence organization. He serves on the nominating committee of The Chronicle’s Visionary of the Year award.

Beyond that, who Conway is depends on whom you ask.

In the tech sector, he’s the dealmaker, the charmer, the guy with the impressive Rolodex who younger entrepreneurs are told they ought to know. While Conway, 66, has been nicknamed the “Godfather of Silicon Valley” with a surrounding “Rontourage,” people such as Susan Hobbs, a venture capitalist at CrunchFund, describe him in more human terms.

“He’s the grandfather,” she said. “Ron tends to be someone who almost everyone I know really does like him and believes he is doing good.”

In City Hall, meanwhile, he is often perceived as a symbol of the greed and money of the tech sector, a reputation that has only grown during the current mayor’s race. Lee was criticized for being too cozy with Conway, especially when it came to Conway’s pet issue, the “Twitter tax break,” a payroll tax exemption that encouraged tech companies to fill a derelict stretch of Mid-Market.

Soon after Lee died of a heart attack in December, Conway stepped up as a patron of Board of Supervisors President London Breed, who took over as acting mayor. Then San Francisco’s progressive supervisors orchestrated a plan to replace her with Mark Farrell, a wealthy white venture capitalist.

They were motivated, they said, not by animus toward Breed — a self-made African American woman from a housing project in the Western Addition — but by a desire to block Conway. Supervisor Hillary Ronen made the point publicly in an impassioned speech during the vote to oust Breed.

“I hate to say it, I wish it weren’t so, but those white men are so enthusiastically supporting your candidacy, London Breed,” Ronen said.

Conway says he hardly ever sets foot in City Hall. But he doesn’t need to. When his campaign contributions are examined, his financial impact is clear. He relies on independent expenditure committees, which are not subject to the $500 personal contribution limit for city candidates.

He donated nearly $600,000 to San Francisco races in 2012, chipping in $275,000 in contributions and loans to a ballot measure that changed the city’s tax structure for businesses, basing it on their gross receipts rather than payroll. The change benefited companies that earned little revenue but had lots of employees — namely, tech startups.

Conway also was angered when four progressive supervisors voted in 2012 to let Ross Mirkarimi keep his job as sheriff, in spite of a domestic violence conviction. He poured $29,000 in cash and $20,000 in-kind contributions into an independent expenditure committee called San Francisco Women for Accountability and a Responsible Supervisor, designed to punish former Supervisor Christina Olague for her vote. Olague, who was appointed by Lee, was facing a tight race against London Breed for the District Five seat.

Two years later, Conway pitched in $85,000 to defeat David Campos, who also voted to retain Mirkarimi, in his unsuccessful bid for state Assembly. Conway then threw $200,000 at an independent expenditure committee to trounce Jane Kim, another Mirkarimi ally, in her 2016 state Senate race against the moderate Scott Wiener.

Nathan Ballard, a longtime friend who has provided consulting services for Conway, characterized the tech mogul as a man of fierce loyalty and lasting grudges.

“If he picks you as the person who is going to carry his issues forward, then he’s going to be in your corner,” Ballard said. “But if he views you as someone who has betrayed him, and betrayed the moderates, you will be punished.”

Ballard recently found himself the target of Conway’s ire for serving as an adviser to Farrell. Conway was livid, and Ballard said the two of them haven’t spoken since.

Others in City Hall note that Conway’s influence extends beyond campaign contributions. The tech investor was embroiled in a years-long debate over the city’s regulation of Airbnb, one of his best-performing investments.

When city Treasurer Jose Cisneros decided in 2012 that Airbnb and other short-term rental services should be subject to the city’s 14 percent hotel tax, Conway rallied tech companies to speak out against the tax at a City Hall hearing. Lee took their side.

So it’s no wonder that progressives see Conway as a political bogeyman, hell-bent on tipping races in favor of tech-friendly candidates. To the moderates, he’s a kingmaker and occasional pest — prone to angry text messages, persistent phone calls and all-caps emails, which he sometimes sends to many recipients.

Some observers say the darker side of Conway’s reputation gave Farrell and the progressive supervisors political cover when they voted to unseat Breed and replace her with Farrell.

During her speech before the board’s vote, Ronen scorned the “tech moguls and real estate billionaires” who had supported and advised Lee, and said that they’d all gravitated to Breed.

Ronen said in an interview the next day that her comments referred to “Conway and his team,” and that they’d threatened to ruin the careers of city officials who didn’t back Breed — allegations that Conway later denied.

“Ronen’s speech struck a very populist tone,” said Jason McDaniel, an assistant professor of politics at San Francisco State University. He noted that to the progressives, Conway is an easy, catchall symbol of capitalism, gentrification and the eviction crisis — everything they say is destroying the city’s character.

Breed, he said, hadn’t done enough to portray herself as independent from Conway, who began stumping for her just days after Lee died.

“On Breed’s side, they just didn’t see how Ron Conway would be a rallying cry for the progressives,” McDaniel said.

When asked how he sees his involvement in the mayor’s race, Conway said he’s donated the allowable $500 to Breed’s campaign and doesn’t have plans for much else. Right now, he said, all of his energy “is on the national level,” as he focuses on gun control and immigration.

Asked if he had any resentment toward Mark Farrell, he paused.

“He’s our mayor,” he said. “I don’t have any further comment.”

In several interviews with people in Conway’s circle — from young entrepreneurs he’s invested in to tech moguls and music stars — many were surprised to learn how Conway is resented by some in City Hall.

Entrepreneur Gautam Sivakumar’s experience with Conway, whose firm invested in his company Medisas, is representative of many. A few years ago he found himself stuck in London because of a visa issue. Within hours, Conway put him on an email thread with the U.S. ambassador to Britain, who swiftly solved the problem.

“In my experience, it comes down to, when I need help and if I ever need help, Ron and SV Angel are there,” Sivakumar said, referring to Conway’s venture capital firm.

Though Conway, who got his start in Silicon Valley as a computer-chip marketer, is valued for the connections he’s able to make, his relationship with others in the industry isn’t always smooth.

Doug Leone, a partner at Sequoia Capital, which has worked with Conway for nearly 20 years, told Fortune in a 2012 profile that their relationship was “good 90 percent of the time.”

“Ten percent of the time it is less than good,” he said.

Salesforce CEO Marc Benioff couldn’t help but laugh at the notion of Conway serving as “the voice of tech” in City Hall. “No one should have a fear that he is a pied piper for Silicon Valley,” said Benioff, who has worked with Conway on philanthropic ventures.

Benioff said he has disagreed with Conway on the Twitter tax break and other issues, on which he declined to elaborate.

“He is evangelizing engagement, and I think that is a good thing for this city, and he is encouraging the tech companies to become engaged,” he said. “He really cares about politics, where I think a lot of businesspeople don’t have as much passion ... and that is something that I respect.”

But when it comes to politics, does he involve himself in the right way?

“I would say not always,” Benioff said. “But I would say that not everyone approaches things in the right way.”

Conway is also being sued by his former partner at SV Angel, David Lee, who says Conway is withholding millions of dollars from him. Lee declined to comment.

After the split with Lee, Conway’s son Topher seems to have taken the lead in day-to-day operations at SV Angel, according to several people Conway has backed. Conway says he still spends the majority of his time mentoring entrepreneurs.

“It’s the thing I most enjoy,” he said.

Paul Graham, co-founder of Y Combinator, a tech accelerator that has long jointly backed startups with Conway’s fund, said he used to tell his startups that if they were going to be big, they needed to have Conway as an investor.

Having Conway’s attention — no matter how scattered it is — is a blessing for anyone looking to make it, he said.

But when it comes to politics, “I could totally believe he seems like a pain in the ass,” Graham said. But, he added, “I’d rather have Ron kicking me in the butt than someone else, because I know he has the right motives.”