Baltimore Comptroller Bill Henry thought long and hard about a request from a few Baltimore City power brokers, one that had been bouncing around a few tight-knit political circles: Run for mayor. But despite the closed-door coaxing and poll results that Henry believed showed a pathway to City Hall’s top office, Henry decided to run for reelection next year.

“The fact of the matter is that I like Brandon personally and I do agree with him on so many of the things that he is trying to do,” Henry said during a flying disc golf round in Druid Hill Park last week. “I just didn’t feel like I could be sincere in campaigning against him when I do agree with the goals.”

“Instead, what I made the commitment to do is work harder from the comptroller’s office, to help take stuff that frankly, the mayor shouldn’t have to worry about, off his plate, so he can focus on the things that we both agree need to be done,” he continued.

His decision to seek reelection is significant as Mayor Brandon Scott remains the sole big-name candidate in the Democratic field.

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Former Mayor Sheila Dixon said she is still contemplating a run. But as summer — when many candidates decide whether to jump into a race — winds down, it looks increasingly like the 2024 race for mayor might end up a two-way rematch of the close 2020 race between Scott and Dixon.

The boosters who hoped Henry would run against Scott made the same basic pitch: Though he may not have the same name recognition as the mayor or Dixon, the 55-year-old Henry turned the historically humdrum comptroller’s race into one of the closest-watched of the cycle by marketing his experience and the potential of the comptroller’s office.

In the wake of former Mayor Catherine Pugh’s resignation amid a corruption scandal, the Henry campaign argued that the comptroller’s office should function as a financial watchdog for city taxpayers. His pitch, coupled with his experience serving three terms on City Council and penchant for wonkiness, won over nearly 55% of Democratic primary voters. Henry ended up defeating Joan Pratt, a six-term veteran, and netted the most votes of any 2020 citywide primary candidate.

Baltimore Comptroller Bill Henry plays disc golf.
Baltimore Comptroller Bill Henry plays disc golf at the Druid Hill Park Disc Golf Course on Friday, Aug. 4, 2023. (Kylie Cooper/The Baltimore Banner)

Consultants from Tidemore, a local Democratic fundraising and strategy firm, who declined to comment for this article, convinced Henry to run for comptroller. Shortly after his 2020 win, more boosters approached him hoping to persuade him to run for mayor.

The group included the Rev. Al Hathaway, who was the longtime pastor of Union Baptist Church, and David Smith, the executive chairman of Sinclair, Inc., according to someone who advised the campaign but was not authorized to speak publicly. The national broadcaster is based out of Cockeysville and operates WBFF Fox45, which airs coverage critical of the Scott administration. Neither Hathaway nor Smith responded to requests for comment.

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Henry largely glossed over the encouragement but began seriously thinking about it this winter, both he and staff aides said. In the spring, he decided to test the water by conducting a poll of likely Democratic primary voters. Pollsters first asked voters if they’d heard of Scott, Henry, Dixon and several other potential candidates, including former TV journalist Jayne Miller, Councilman Eric Costello and attorney Thiru Vignarajah.

The poll tested two descriptions of Henry. One said he was committed to tackling the root causes of crime and making the wealthy pay their fair share of taxes; the other held him up as a fiscal watchdog who brought a data-driven approach to City Hall.

About 8% of respondents who got the fiscal watchdog description said they would support Henry for mayor. But 11% who heard the more populist description said they would support Henry. In both cases, Scott and Dixon both received more than 20% of support, though it lagged somewhat against the populist description.

“The poll didn’t tell me that I couldn’t win a race for mayor,” Henry said. “The poll told me that to win a race for mayor I would have to spend the next year cutting Brandon down on everything.”

But he and the mayor “agree on so many basic goals that I didn’t feel like I could convincingly and sincerely spend an entire campaign knocking him, and I didn’t want to,” he said.

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Still, the comptroller has been unafraid to criticize the mayor, particularly over a controversial agreement with the Baltimore Gas and Electric Co. earlier this year, around the same time he was mulling a run. And he netted his office a bit more power by wresting a small portfolio of responsibilities from the mayor, through a charter that moved City Hall’s troubled vendor payment duties to his office.

Henry probably would have been a bigger challenge to Scott than Dixon, and certainly more than someone with less experience, said the adviser who is not authorized to speak publicly.

Henry still would’ve faced two significant challenges: fundraising and drawing enough of a distinction to Scott.

“The people who are energetically looking for an alternative to the mayor are coming from places that are probably more conservative than both Henry and Scott,” the adviser said.

Scott reported having nearly $451,000 on hand, according to the most recent campaign finance reports, which is more than eight months old. Henry reported having $9,454 on hand.

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Dixon has just under $5,000 in her campaign account. The Baltimore Banner reported last week that Adeo Advocacy, Henry’s current fundraising firm, created a super PAC to support Dixon.

Sophia Silbergeld, a partner at Adeo, said there was incredible donor enthusiasm for a Henry mayoral campaign from his existing base of supporters and those who had never significantly donated to his campaign.

“It was a real cross section of people who are players because they have business interests with the city and who have grown frustrated with the processes in the current administration, and ideological Democratic donors who are frustrated with their perception of an administration that is unengaged in issues that affect people all over the city,” she said.

She declined to name specific donors. The next round of campaign finance reports is due at the end of 2023.

Henry has a vision for his next term: more responsibilities for the comptroller’s office, which also oversees audits, real estate, and telecommunications and postal services for City Hall, particularly responsibilities under the finance department. “The mayor has 99 problems. We have four,” he said, in between fishing a stray disc out of a puddle in between flying disc golf rounds and handing it back to its grateful owner.

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Baltimore Banner reporter Emily Sullivan laughs as Baltimore Comptroller Bill Henry fishes a disc out of a pool of water.
Baltimore Banner reporter Emily Sullivan laughs as Baltimore Comptroller Bill Henry fishes a disc out of a pool at the Druid Hill Park Disc Golf Course on Friday, Aug. 4, 2023. (Kylie Cooper/The Baltimore Banner)

He said he’s pleased that more city residents are now aware of the comptroller’s office and its duties.

“Are we at the point yet where as many people as we like are as informed as we would like them to be?” Henry asked. “No, that’s why we’re going to keep doing this for another couple of years.”

Henry believes he has raised the bar for what people expect from all citywide officials.

“But we’re not going to rest on our laurels,” he said.