Shannon Liss-Riordan spent more than $9 million of her own money in her bid to become the Democratic nominee for Massachusetts attorney general. Less than two hours after voting ended, the primary’s outcome wasn’t even close — Andrea Campbell defeated Liss-Riordan by a stunning 16 points.
“Money,” the great Cyndi Lauper once sang, “changes everything.” Yet often that’s not the case for self-funded candidates. Liss-Riordan is only the latest wealthy candidate who dug deep into their own pockets and still came up empty. That led to a win for Campbell — and voters.
This not to say that Liss-Riordan, a labor lawyer, was unqualified for the job she sought. But unchecked money breeds mistrust in politics, and the exorbitant amounts she kept throwing into her campaign were unseemly. Whether or not the assessment was fair, it smelled like an attempt to buy the nomination.
“I think there’s so much unease and discomfort among regular voters and citizens with [unregulated money in politics],” said Maurice T. Cunningham, author of “Dark Money and the Politics of School Privatization,” published last year. “There’s a whole host of things wrong with the campaign finance system, and this is one of them — there’s a distance between regular donors and people who say ‘I’m in, I can do it myself’ but don’t have a track record with people.”
Even though Liss-Riordan was largely self-financed, “she had 1,300 individual donors. Campbell had 19,000,” Cunningham said. “To me, it exposed the weaknesses of self-financed candidates who quite often come up short.”
This was Liss-Riordan’s second self-funded political campaign. In 2019 she made an unsuccessful bid for the US Senate. In addition to backing from a super PAC, Campbell raised $4 million from donors.
Of course, some wealthy candidates achieve political success. When he ran for Massachusetts governor in 1990, William Weld lent his campaign $2 million.
Then there are the Kennedys. In a 1993 documentary on America’s one-time political dynasty, Thomas P. “Tip” O’Neill, the longtime US House Speaker and Massachusetts politician, recalled the money that family patriarch Joseph P. Kennedy Sr. poured into John F. Kennedy’s first congressional campaign.
“You can be a candidate, you can have the issues, you can have an organization, but money does miracles,” O’Neill said. “And that money did miracles in that campaign.”
Those miracles aren’t what they used to be.
Now senator of Utah, Mitt Romney dipped into his own millions for his presidential campaigns but never reached the White House. Michael Bloomberg, the former New York City mayor, spent $1 billion vying for the Democratic presidential nomination in 2020. He won a single primary — in American Samoa. Bloomberg couldn’t have generated more heat if he’d set his stacks of cash on fire.
Fellow Democratic candidate Tom Steyer, a billionaire businessman, dropped more than $350 million on his failed presidential pipe dream. In Massachusetts, Chris Doughty self-funded his campaign for the Republican gubernatorial nomination but lost the primary to Donald Trump-endorsed Geoff Diehl.
People of great means are accustomed to using their wealth to get whatever they want. But no matter how well they personally finance their campaigns, their money can’t cover other significant shortcomings.
Candidates “are often self-financing because they lack in other political assets,” Cunningham said. “Some haven’t run before, which is harder than people realize. They haven’t reached out to people to build an organization or a donor base.”
In the end, Campbell, a former Boston city councilor, was the better candidate. Despite coming up short in last year’s Boston mayoral primary, she has deep connections with constituents who know her, trust her, and didn’t let her down. Against Liss-Riordan, she won every precinct in Boston.
“Voters become less cynical when they get to meet a candidate and have a conversation,” Cunningham said. “If you’re on a TV ad, well, that’s nice, but it’s a one-way conversation. But if you’re out and you can see that person working for your vote, that has impact.”
Those who donate to campaigns feel personally connected to them. Whether they give a few dollars or hundreds, a donation is an investment in a candidate and the future they offer. Liss-Riordan’s millions could not compensate for the lack of unity between her campaign and voters.
If Campbell triumphs in November over Jay McMahon, her Republican opponent, she will be the first Black woman in Massachusetts history to win statewide office. And while it’s unlikely we’ve heard the last of Liss-Riordan, for now she is left to ponder a $9 million lesson learned about all the things that money can’t buy.