This is the sixth attempt to persuade voters to undo the state’s flat income tax rate. Each previous time — 1962, 1968, 1972, 1976, and 1994 — proponents lost in a landslide. While some of the dynamics of the failed 1994 campaign exist today, there are critical differences that would suggest the sixth time might prove to be the charm for proponents.

“We were out-staffed. We were out-advertised. It was a tough situation,” recalled Peter Enrich, an emeritus professor of tax law at Northeastern University who was involved in the 1994 effort and serves as an adviser to today’s Question 1 proponents.

This go-round, backers of the tax measure have raised about $24.8 million, almost exclusively from education unions, while the opposition — bankrolled by the business community and wealthy individuals — has $13.7 million, according to state campaign finance filings.

In 1994, opponents outspent proponents by a 3-to-1 ratio.

It also doesn’t take a political genius to seize on a fatal flaw of the 1994 campaign: asking voters to support a two-part ballot initiative on an issue as complicated and controversial as taxes. Question 6 would have amended the state Constitution to adopt graduated rates, while Question 7 would have set new personal income tax rates.

Proponents figured they had a strong case to justify such an elaborate strategy: The measure would represent a tax cut for 92 percent of taxpayers. Early polls showed support for the “grad tax,” but the more voters heard about it, the more confused they became. The last poll, released days before the November 1994 election, showed the initiative was on track to lose.

“One of the general lessons that I think people have learned about ballot questions over the years is that complexity is a real hurdle,” Enrich said. “Given what general attitudes were in the ‘90s, we were trying to do too much.”

Today, voters only have to answer a single question about a constitutional amendment, and it’s been distilled to a simple concept: increase taxes on people who make more than $1 million a year. This would affect roughly 26,000 households — or less than 1 percent of taxpayers ― by adding a 4 percent surcharge to income over $1 million.

Jim Braude, who led the alliance that supported the 1994 graduated tax, hails the strategy as “smart.” In particular, Question 1 links higher taxes to funding education and transportation improvements. The 1994 proposal, however, was not intended to raise revenue. As a result, it felt more like an exercise in redistributing wealth by increasing taxes on the top 8 percent of households.

“You’re not endorsing an abstract concept. You’re endorsing something very concrete,” said Braude, who is now a popular radio and TV host on WGBH. “The question itself is constructed in a way that is far more appealing and far less scary to voters than anything that’s been done before, including my effort in ‘94. They really did it brilliantly.”

The organizers of Question 1 are also benefiting from a propitious moment in Massachusetts politics: The anti-tax movement lacks high-profile champions.

In 1994, they had two: Barbara Anderson and Bill Weld.

Anderson, the sharp-tongued head of Citizens for Limited Taxation, was in her element. She had led a series of successful ballot questions that reduced taxes, most notably Proposition 2½ in 1980, which capped property tax increases at 2.5 percent of a community’s total valuation.

By many accounts, Anderson was the state’s most powerful unelected official. Allies dubbed her a “tax-cut tigress,” while foes labeled her a “tax-cut terrorist.” And when it came to defeating the graduated income tax, she took a no-prisoners approach by tapping into a mistrust of government and portraying the initiative as a scheme by liberals and public employee unions to eventually raise taxes on everyone.

“There are three reasons to oppose the grad tax: One, you can’t trust the Legislature; two, it’s bad for the economy; and three, you can’t trust the Legislature,” Anderson told the Globe in May 1994, right after lawmakers voted to put the graduated tax on the ballot.

This time, the opposition doesn’t have Anderson to denounce new taxes at every turn. She died from leukemia in 2016 at age 73.

Anderson’s distaste for taxes was perhaps matched only by Weld’s. At the time, he was running for a second term as governor and cutting taxes was a cornerstone of his campaign. The Republican was a staunch opponent of the graduated tax and railed against it with a memorable one-liner, calling the measure a “Trojan horse.”

“I majored in classics and I think I know a Trojan horse when I see one,” Weld told the Globe, adding that the proposal was “designed to secure the admission of the grad tax within the gate.”

In November 1994, Weld garnered a whopping 71 percent of the vote; his victory margin was similar to the losing margin for the grad tax, with a lopsided 69.6 percent of voters against. By being on the ballot, Weld brought out like-minded constituents and got out the no vote.

Weld, who went on to run for president and is now a lawyer at Mintz Levin, remains fiercely opposed to a graduated tax. He will vote no on Question 1.