A Tale of Two Frontrunners: The Similarities of the 1993 and the 2021 Boston Mayoral Election

It is less than two weeks from Boston’s mayoral election, and for Michelle Wu, it is her race to lose.

The city councilor finds herself in a very strong position, as recent polling and fundraising detail how she has cemented herself as the top candidate over fellow city councilor and rival, Annissa Essaibi George.

The most recent poll, released by NBC10 and Suffolk University, showed Wu with 62% and Essaibi George with 32% with the former leading with White, Latino, Black, and Asian American Pacific Islander voters by double digits.

What is interesting with this poll isn’t just Wu’s 30-point lead. If these results manifest on November 2nd, she would come very close to matching the winning margins of Mayor Tom Menino in his first Boston mayoral election in 1993.

Menino’s victory also took place on November 2nd, 28 years ago, as he managed to beat then Massachusetts State House representative, James T. Brett by 28 points. He would then go on to become Boston’s longest-serving mayor before his retirement in 2013 and his eventual death in 2014.

One would think that similarities between the 1993 and 2021 elections would stop there. Yet, both elections tell a very similar story in how they began, how the front runners are running their campaigns against their rivals, and maybe, how the future will look.

To begin with, both races start very similarly: with the President of the United States tapping the current mayor to serve in his administration.

In 1993, then Mayor of Boston, Raymond Flynn resigned during his third term to serve under the Clinton Administration as the United States Ambassador of the Holy See. In 2021, President Joe Biden tapped Mayor Martin J Walsh to be the United States Secretary of Labor.

Both mayors had very close relationships with the presidents of their time. Flynn helped court pro-life Catholic voters to secure President Bill Clinton a victory in the 1992 election. Walsh and Biden were both from Irish families and had close ties to unions and union groups, creating a very close friendship.

When the Mayor of Boston resigns, the city council president would step in to become the acting mayor. In 1993, that was Tom Menino. In 2021, the City Council president was Kim Janey.

1993 was not planned to be a Boston mayoral election year, as Boston mayors served a four-year term, and, if not tapped, Flynn would not have been up for re-election until 1995.

In 2021 however, Walsh was up for re-election, and it was no secret to reporters and analysts that city councilor Michelle Wu was going to jump in and challenge him. Walsh in fact anticipated this, and pulled the rug from under Wu’s feet by announcing to the Boston Globe that she was running before she properly kicked off her Boston mayoral election campaign in September.

Wu would not be the only candidate to jump in before President Biden had tapped Walsh for Labor Secretary, as Ward 4 city councilor Andrea Campbell announced she was running that same month.

Either way, the races did become ones without incumbent mayors, as both races became incredibly crowded, a common staple of Massachusetts primaries.

Unlike Menino, Wu was not the acting mayor, and could not use that as an advantage point as he did. She did, however, use a different aspect that Menino brought up to court voters: their time in the city council.

Yes, Kim Janey, Boston’s first black female mayor was given a gift of a pseudo-incumbency much like Menino. Menino, however, built a name for himself in the city council as a man who knows every place in Boston, from Hyde Park to Dorchester, as well as becoming one of the most powerful and influential members of the council itself, heading the Ways and Means committee.

Menino also led the charge taking on social issues at the time such as the AIDS crisis and the increase in homelessness in Boston and had adamantly made his point that he was “more progressive than most progressives” in a Boston Globe column in 1993.

Wu has also built a career of taking on social issues and shaping a progressive policy in the city council, whether it be calling for more action to take on climate change, calling for a free MBTA, and just like Menino, call for more housing and help for the homeless in the city.

The election makeup of 1993 was of course different than 2021, as Boston still had a high population of working-class white voters at the time, as well as different issues making the headlines, such as crime being a more pressing concern for voters in 1993.

That doesn’t mean that there weren’t other overarching issues that still resonate with the two front runners today. One of the big talking points in both campaigns is the topic of Boston Public Schools. Menino discussed how he would see students protesting over the lack of quality in their schools, and ran fiercely on the issue to ensure better schools and school materials for children.

Wu and her rival Essaibi George took a different approach. Rather than be the observer of kids with inadequate schools, the two of them had connections to those students as mothers of children who went to Boston Public Schools.

What’s different about the two candidates, though, is what they are calling for in the public schools. Essaibi George in an interview with WGBH News said the schools need “Stability and predictability,” where Wu, much like Menino, wants to change the status quo and call for more school equity, and claims that it can be accomplished through politics. Wu said to WGBH, “We are a city where the barrier has never been financial resources or expertise or helping hands ready to partner from the community’s side. The resource barrier has always been around political will.”

The two front runners also managed to cement their statuses as front runners fast in the primary and managed to create a large gap between them and their opponents in the upcoming general election. Before the primary, Menino gained support from multiple African American politicians and groups to help build his collation, and while Wu originally struggled with gaining these voters, she did keep making visits and talking to voters in neighborhoods like Roxbury and Mattapan, which would lead major black leaders such as Tito Jackson and Kim Janey to endorse her over Essiabi George after both Janey and Andrea Campbell would not make the final two.

There is even some national overlap between these two election years, as outlets like the Washington Post and New York Times noted the historical significance of the candidates. The winner of the Menino-Brett race would be Boston’s first non-Irish mayor in 60 years. In the Wu-Essaibi George race, the winner would be Boston’s first female and person of color elected mayor, showing that the voters and ideals in Boston were changing.

As for the future? Well, if Wu is elected mayor, she might butt heads with the city council over getting ideas such as a free T or more affordable housing passed, but this wouldn’t be a new feeling in Boston city politics. Menino had a horrid relationship with the city council, and would often use a bully pulpit to get around them and get his ideas across towards the city’s residents. While Wu might not have the same sourness towards the city council as Menino, having a bumpy relationship seems inevitable.

Nevertheless, the shadow of 1993 hangs over 2021’s Boston mayoral election. For Michelle Wu, she seems to welcome this comparison, as in a recent mayoral debate, she name-dropped Menino as who she looks to for inspiration. After all, before joining the city council in 2014, she worked for the former mayor, and remembers what he told her: “we can do the big things by getting the little things right.”