An influencer has Bill Ferguson stressing. Should he be?

When Bill Ferguson pulled up in early May to campaign in South Baltimore’s Cherry Hill neighborhood, the Maryland Senate president brought some heavy hitters with him.

He and Mayor Brandon Scott tossed a football with their respective sons for an endorsement promo at the recently redone Middle Branch Fitness and Wellness Center. Then Ferguson went house-to-house with a group of high-powered campaign volunteers, including City Councilwoman Phylicia Porter and J.D. Merrill, Scott’s chief of staff, to try and woo Democratic voters to his side ahead of the June 23 primary.

Electorally, the Senate president is among the most unbeatable politicians in Maryland — the last person had the job for 33 years and only gave up the gavel because of failing health. Ferguson’s only challenger in 16 years got fewer than 1,000 votes in 2014. A mild-mannered former school teacher, Ferguson is arguably the most powerful lawmaker in Maryland. Schools, roads, bridges — that fitness center — are built because he wants them to be. Laws are passed, or not, at his discretion. He’s stood up to Gov. Wes Moore more than once.

But these days, Ferguson’s stressing. The tension between the compromising Ferguson and his more uncompromising, increasingly left-wing primary electorate has come to a head.

For years, Ferguson’s made deals in the legislature or held up progressive bills around immigration and juvenile justice as a means to govern his chamber. President Donald Trump’s return to the White House last year only further split Democrats over how to respond.

And in the fall, Ferguson came out against midcycle redistricting, splitting with Moore and then-House Speaker Adrienne A. Jones, further frustrating voters who already saw him as slow to act. (After the U.S. Supreme Court threw out portions of the Voting Rights Act, Ferguson said last week he was open to redrawing the maps for 2028.)

This has left the Senate president in an unlikely spot: a contested race for the General Assembly’s 46th District against an unlikely opponent.

That would be Bobby LaPin, a hoodie-clad, flip-flop-wearing charter boat captain-turned-social media influencer who, as one Democratic strategist put it, looks like he “should be holding up a barstool down at Cat’s Eye Pub” in Fells Point rather than serving in the state Capitol.

Ferguson pitched the primary election as an opportunity to reintroduce himself to voters.

“It’s regrounding,” Ferguson said. “One of the challenges of being a presiding officer is that I’m often most successful by giving credit to others. I have to get into the habit of ... talking about things I have gotten done as opposed to what we do and what others have done.”

Alli Smith, Ferguson’s campaign manager, was blunter about their mission.

“He should crush the opponent, not eke out a win.”

But LaPin, part of a wave of populist newcomers seeking to reshape traditional party politics, is proving to be no slouch.

It’s a cycle that has repeated throughout recent U.S. elections: North Carolina’s GOP Senate president lost his primary earlier this year; then-unknown Alexandria Ocasio-Cortez knocked off Joe Crowley, a member of U.S. House Democratic leadership, in a 2018 New York primary; now-New York Mayor Zohran Mamdani used social media and a socialist platform to beat former Gov. Andrew Cuomo last year; and Graham Platner has mounted an insurgent Senate campaign in Maine.

LaPin’s strength is his online audience. The influencer is running a viral campaign from Ferguson’s left and has nearly 150,000 followers across Instagram and TikTok; Ferguson has fewer than 3,300 on Instagram and doesn’t have a TikTok.

LaPin, also known as “Captain Bobby,” cultivated his following in recent years under the username “Sail Local.” He found local celebrity making content on an array of topics, from lighthearted skits about picking up women by being able to afford eggs to videos of Baltimore sunsets from his boat, the SAEDA.

They aren’t all viral hits: A pandemic-era YouTube series called “Bobby’s Friday Love Songs,” featuring him playing guitar and singing while scantily clad, kind of flopped.

The posts became more political about a year ago as LaPin grew more outraged by Trump’s administration. LaPin started weighing in on state and city issues — utility bills, the looming threat of the National Guard being dispatched to Baltimore, the federal government shutdown, affordability.

As LaPin got more political, commenters started encouraging him to run for office. He made a video about Mamdani’s win, suggesting it “could be the beginning of change all across America.”

At that time, a letter Ferguson wrote to his fellow state senators outlining why the body would not take up midcycle redistricting became public. National Democrats who supported redistricting, including Moore, were outraged.

On Nov. 7, LaPin made a video critical of Ferguson’s decision. Four days later, he made an emotional video weighing whether to run for office. Then on Nov. 14, LaPin made a third video, this one announcing he would challenge Ferguson and, by extension, corporate greed and machine politics.

“Working people have carried this city on their backs while lobbyists have carried their wish lists into rooms where decisions are made,” LaPin told his followers. “This is bigger than just fighting Bill Ferguson. This is about a system that speaks in a language of progress but keeps power where it’s always been.”

LaPin’s online support has translated to the real world. He raised $52,000 in his first two months, entirely from small dollar donations (LaPin does not accept corporate donations). Two of those were from members of Moore’s administration, which rankled Ferguson. LaPin’s yard signs dot Southeast Baltimore neighborhoods like Canton, Fells Point and Patterson Park.

The captain feels the momentum, too. In an interview, he said that his videos on affordability, immigration and reining in corporations like Baltimore Gas and Electric have shaped the tenor of the race. Ferguson, LaPin said, is being forced to respond.

“I’m in his head. Of course. The proof is in the pudding,” LaPin said.

But LaPin’s fight is uphill. Ferguson has nearly $1 million in his campaign account, plus another $578,000 he could tap from the Democratic Senate Caucus Committee account. Already, Ferguson has spent more than $350,000 in his campaign against LaPin, more than twice what LaPin has raised so far.

Ferguson is campaigning with fervor — meeting daily with constituents and attending neighborhood meetings. That includes Democratic voters who don’t like him.

In mid-May, Kelly Quinn, an organizer in the Riverside neighborhood, hosted a small gathering of about a dozen fellow progressives to meet Ferguson and, essentially, grill him. Quinn, who said she has been “disappointed and alienated” by Ferguson’s staff in Annapolis because they would not return her calls, set up the gathering at his campaign manager’s request.

“I was intrigued that a campaign official would even want to do that, or a candidate would be willing. Because I’m really interested in how a candidate makes up and then changes their mind,” Quinn said.

Most people there, Quinn assumed, planned to vote for LaPin. They had grown frustrated with Ferguson over the past five years because of what they viewed as him singularly holding up the progressive agenda, including a bill to stop children from being automatically charged as adults and one to ban state and local law enforcement from entering into formal cooperation agreements with U.S. Immigration and Customs Enforcement.

This year, both bills, along with a series of other progressive legislation, became law after years of failure.

Ferguson spent the evening listening calmly, even when told people were suffering because of “your inaction,” Quinn said. He “talked about his own regret and, in some cases, how he was able to lead with changes this year,” Quinn said.

Some people even came away convinced they could vote for Ferguson — though no one requested a yard sign.

“I was on the fence going in. I feel much more comfortable,” Quinn said.

“I’ve been searching who I can vote for and not just against. And I feel much more comfortable voting for him now.”

As for Ferguson’s opposition? Quinn extolled the virtues of competitive primary elections before conceding that, while she liked LaPin’s passion for certain progressive causes, she didn’t find him to be “serious” in the way Ferguson is.

Len Foxwell, a longtime Democratic strategist, was blunter in his assessment: “There’s no evidence to suggest he’s prepared to serve in the Maryland state Senate in any way. It doesn’t mean he couldn’t learn ... but right now, Bobby LaPin is a political blind date.”

The race isn’t about whether LaPin would do well as a senator, Foxwell said, but whether Ferguson has done well enough.

That dynamic has played out at community meetings across the district.

At a candidate forum in Locust Point, LaPin spent the evening attacking Ferguson for everything from taking BGE money to the delay of the Key Bridge rebuild. At a meeting in Graceland Park, a neighborhood on the border of Baltimore and Dundalk, LaPin contrasted their approaches by positioning himself for the people and Ferguson for special interests.

Ferguson’s record is both a weight around his neck and his biggest strength.

In Cherry Hill, he and Porter, the councilwoman, spoke to residents about the money he’s secured for needed Hanover Street Bridge improvements. In Graceland Park, he spoke about getting more funds to redevelop nearby O’Donnell Heights and build a park there. In Locust Point, Ferguson spoke about how many schools he’s gotten money to build.

“That doesn’t happen because somebody posts a video,” Ferguson said then. “It happens because people show up and they do work, and they build a coalition, and they get stuff done.”

At an event in Canton, Ferguson started his remarks by acknowledging that LaPin, who was speaking after, would call him a “career politician” and talk about his corporate support, his participation in the political machine or how he’s done “some horrible thing.” All of that is fine, Ferguson said. He didn’t want to waste time rebutting all of LaPin’s attacks.

“What I would like to do is talk about my record,” he said. “About how I’ve served you the last 16 years.”