Analysis: Why Boston is going to make history Tuesday night

Pindell: This is a good place to start. If people around the United States wanted to sound smart about the Boston mayoral race and just use a single word to describe it, that word would be: “historic.” Boston has held elections for mayor since 1822, before half of American states were even states. A White man has won every single election.

In 2021, the four front-runners for Boston mayor are four women of color. A Black man is in fifth place.

This historic change has driven the conversation about the race locally and nationally and rightly so. But was this a surprise for veteran Boston politicos? No, at least once it became clear that the previous mayor, Marty Walsh, would leave to serve as Biden’s Labor Secretary.

Even before Walsh got tapped by Biden, two council women of color (both had previously served as council president) were already running for mayor. Boston is a majority-minority city that last elected a Republican mayor 95 years ago and there is a hunger in the city for a diverse mayor. And a White person at that [stage] would have to enter a contest against two women of color who have stature already, and a Black woman who was the acting mayor and weeks from entering the contest herself.

Cillizza: Is there a liberal vs. moderate dynamic playing out here? Or some other split or dynamic that differentiates the field?

Pindell: Not really. There are ideological differences, but they are subtle. For example, affordable housing is a top issue in the election. One study found Boston is the second most expensive city to buy a home in the United States, behind San Francisco, but ahead of New York City. Before the pandemic, it was the third most expensive city to rent in, but apparently, it dropped to fifth last year. There is a sizable chunk of Boston residents who spend half of their income on housing.

I mention this because it’s the backdrop for probably the biggest difference in candidates: the woman topping the polls, Councilor Michelle Wu, a protege of Elizabeth Warren, wants rent control, while the others reject it for one reason or another.

Note we aren’t hotly debating other issues that fit neatly on the moderate/liberal scale such as defunding the police, tax cuts, reparations, Covid mandates, or other items you see debated in other city elections this year.

Some in the media have tried to suss out that Councilor Annissa Essaibi George is a moderate given her strong backing from law enforcement. And her pitch is “Common Sense for Boston.” At the same time, she doesn’t really differentiate on issues except for the need to hire more cops, but even that isn’t the main thrust of her campaign. She is no [New York City Democratic mayoral nominee] Eric Adams. She also notes she is the only candidate running who backed Ed Markey for Senate over Joe Kennedy last year.

Cillizza: Many of these candidates rose through the Boston political class as a sort-of team. Has that affected the way the campaign has played out?

Pindell: Totally. All four women front-runners are all city council members. Three have served as council presidents. The fifth, John Barros, was also part of the system as an aide in the Walsh administration. The point is that none of them are outsiders and none of them can really cast blame on a particular person. This is especially true since the items being discussed on the campaign trail are systemic (schools, racial justice, addiction, gentrification, climate resilience) that all candidates are, in a way, to blame for not fixing.

In tone, the race has had some “blunt elbows” between candidates and Super PACs, but no fists. That they all have worked together for years is probably the biggest reason why.

Cillizza: What is the general mood in Boston? Are voters happy with how things are going? Or is that a shake-up-the-status-quo election?

Pindell: Despite the systemic issues mentioned above, this is not the classic definition of a change election.

Boston has a world-class economy in terms of growth. In fact, it is undergoing the largest building boom in the city’s history and neighborhoods have been transformed, especially including my own in South Boston. Voters aren’t faced with bad choices, but instead about how to spend all this new property tax money and how to level out many inequities in the city, especially as it relates to race and class. Four years ago my colleagues at the Globe Spotlight team found the median net worth for a White Boston household was $247,000. For Black families, it was $8. [Note: This is not a typo.]

Still, no one is in the mood to throw the bums out (though, again there is no outsider even offering that choice.) There is a sense that a different background leading the city could lead the city to change, but not wholesale change.

Cillizza: Finish this sentence: “The two candidates MOST likely to advance to the general election in November are __________. ” Now, explain.

Pindell: Given the state of the polling industry, I am hesitant to really go here. But the trendlines of several polls are clear on two points.

First, Wu appears to have secured one of the two spots that will go on to the November run-off.

Second, there is a three-way race for the other slot that is really too close to call. Those competing are Essaibi George, Acting Mayor Kim Janey and Councilor Andrea Campbell.

I can make a compelling argument as to why all three can get second. But when we are talking about how you need just 25% support to move on, smarter people than me on this race, constantly point out that Essaibi George has her own set of voters. So I will take a stand and be willing to bet $5 on Essiabi George. (But not $10 dollars or $10,000 as some former Massachusetts politicians are willing to wage.)

If that happens, the post-game analysis will be on how Janey, handed one of the biggest gifts in state politics in decades by being lucky on timing to be the acting mayor and during a pandemic, failed in a Martha Coakley way.