If history is any indicator, the fate of six members on the Baltimore City Council might as well be written in stone.

Voters filling out ballots this year are being asked whether to cut the City Council from 14 districts down to eight, eliminating nearly half of jobs on the legislative panel. Baltimore voters tend to approve ballot questions almost automatically — only one in the last 25 years has failed.

But in the final weeks before Election Day, City Council members, progressive groups and labor organizations are escalating a campaign aimed at convincing people to vote against Question H. Around town, signs are cropping up in yards. Opponents knocking on doors and attending community meetings dutifully inform residents that the measure is financed by David Smith, the Baltimore County-based media mogul who chairs Sinclair, Inc. and earlier this year bought The Baltimore Sun. In recent weeks, a well-funded counteroffensive backed by Mayor Brandon Scott — the pointedly named Stop Sinclair — has blitzed tens of thousands of residents with text messages and radio ads.

But could this late-stage push prove too little, too late?

The effort to block Question H is the most robust ballot measure opposition campaign in memory, said Andy Ellis, a member on the city’s Charter Review Commission who is leading one of numerous coalitions dedicated to stopping the proposal. Smith similarly financed a referendum two years ago to install term limits at City Hall. The measure was approved, but won the least support of any question on the ballot.

If Question H does pass, it will be by a narrow margin, Ellis predicted. That outcome could mean some pangs of regret for the opposition. Some 60,000 city residents received mail-in ballots late last month, and if there’s any missed opportunity, Ellis said it will be that the opposition didn’t ramp up its messaging campaign in time to reach all of those voters.

“I do feel comfortable. I don’t feel confident,” he said. “I think there’s a decent chance on Nov. 6 we look back and say, ‘Eh we could have beat this thing.’”

Whether Question H is approved or rejected has big implications for the future of politics in Baltimore.

Success could usher in a new era of power in the city, in which wealthy donors like Smith and grassroots coalitions alike bypass City Hall to make sweeping reforms through the ballot. If the question fails, it could demonstrate the power of public messaging to turn the tide against referendums.

Opponents insist that just about everyone in Baltimore who has heard about Question H plans to vote against it — a claim backed up by the coalition’s polling. According to Stop Sinclair campaign correspondences reviewed by The Baltimore Banner, an overwhelming 57% of respondents to a campaign survey planned to vote against Question H, while only 6% said they planned to vote for it. Though that survey relied on a small sample size taken months ago, it found another 26% of respondents were undecided and 11% needed more information.

But many still haven’t heard the opposition’s message.

Volunteers knocking on doors on a recent Sunday in the leafy, and pricey, Homeland neighborhood were having more luck than usual getting people to answer. But as of Oct. 20, the group, organized by Councilman Zeke Cohen, had knocked on just over 1,600 doors since the start of the month, talking face-to-face with fewer than 600 people. Though nearly everyone the canvassers have met says they intend to vote against Question H, they represent less than .2% of Baltimore’s registered voters.

Councilman Mark Conway, who joined the Homeland canvassers, explained to constituents that a smaller City Council would make him much less accessible. If the council gets slashed in half, he argued, their city services are going to suffer.

For at least some residents, the case for keeping the 15-member status quo can be nuanced. One woman walking her dog wondered if reducing the size of the council might make sense considering Baltimore’s decades of population decline? Another assumed Conway was there to talk about a different, high-profile ballot measure.

“Is this the one about the harbor?” asked a woman who answered the door for Conway. The Homeland resident briefly listened to the councilman’s case against shrinking the City Council, but soon steered conversation to Question F, the referendum that would make way for the nearly $1 billion proposed redevelopment of the downtown waterfront.

So far, Smith has sunk $415,000 into the group pushing Question H, People for Elected Accountability and Civic Engagement. But the Sinclair exec hasn’t put any new money into the effort since February, and PEACE reported this week that it has barely $200 in the bank heading into the homestretch before the election.

The bulk of PEACE’s spending happened close to a year ago, including to pay canvassers to get signatures for the petition that qualified their measure for the ballot. The Baltimore Banner has interviewed dozens of those signers and found that many don’t recall endorsing the ballot question — or now say they disagree with its intent.

Still, a few residents vented frustration with City Hall and urged change.

“Shrink it. Shrink it to the bare bones,” said East Baltimore resident Oletha Carter, who singed PEACE’s petition because she feels the council has no interest in serving its constituents.

PEACE chairman Jovani Patterson said he anticipates his committee will get more money before the election, but he also acknowledged he’s mostly letting things play out organically.

At the same time, Patterson criticized city leadership for its organized effort to block his proposal. When it comes to resident frustrations with city government, elected leaders fail to jump into action, Patterson said. But “when the people say that we should have a voice in how our government is structured, the powers of government essentially goes into protect mode.”

The Stop Sinclair committee reported more than $155,000 in the bank earlier this month, drawing on large donations from labor groups, as well as contributions from the mayor, six City Council members and one incoming member: Odette Ramos, Danielle McCray, Phylicia Porter, Ryan Dorsey, Sharon Green Middleton, Cohen and 8th District Democratic nominee Paris Gray.

The group reported Friday that it has spent more than half of that early October balance.

According to the internal Stop Sinclair emails reviewed by The Banner, the group recently sent anti-Question H texts to roughly 181,000 voters and earlier in the month spent $74,000 on radio and online advertising. Stop Sinclair anticipated sinking another $25,000 in advertising on Black radio stations, targeting a demographic that accounted for a disproportionate share of those who signed PEACE’s ballot petition, according to a Banner analysis.

Reaching voters just before they go into the polls, during early voting and on Election Day, is an important part of Stop Sinclair’s strategy, according to the messages. The group is planning to make last calls to mail-in ballot voters and blast out another round of text messages on the weekend before Election Day.

Like others in the anti-Question H coalition, Cohen expressed confidence that residents who know about the proposal don’t want it. But the East Baltimore councilman acknowledged that too many people still haven’t heard their case. That’s partly because the referendum didn’t have a name until a few weeks ago, making it tricky to wage a full-force awareness campaign, Cohen said.

While the Stop Sinclair campaign has painted Smith as the villain and mastermind behind Question H, some on the City Council have shied away from that framing.

“For me, it’s less about the single person that funded the ballot question, and more about the incredibly negative impact that it’s going to have on voters if it were to pass,” said Cohen, the Democratic nominee to become Baltimore’s next City Council president.

Still, antagonizing Smith has proven an effective strategy for City Hall before. Some saw Scott’s convincing victory in the Democratic primary over Smith’s preferred candidate, former Mayor Sheila Dixon, as a rebuke of the Sinclair executive’s meddling in city politics.

For at least one attendee at a recent community meeting in Park Heights, the David Smith-factor changed his mind about Question H.

Rudy Merrick, a retired U.S. Postal Service employee who has lived in the area for more than three decades, had been planning to vote for Question H. Merrick said he doesn’t feel represented by the City Council and finds the mayor ineffective. He voted for Dixon, Smith’s candidate, in the Democratic primary.

But when a volunteer with the opposition’s Baltimore City Is Not For Sale coalition stood up at the meeting and railed against Smith, it caught Merrick’s attention.

He didn’t know Smith’s name before the meeting. But when he heard the opposition’s case that the Sinclair exec is angling to “take control” of the city, he explained, “I was pretty convinced by that.”

Baltimore Banner reporter Lee O. Sanderlin contributed to this story.