I find it fascinating to examine where the money for each of these candidates comes from - how much is from Massachusetts, how much is from Boston, what’s the average donation, what neighborhoods most of the donations come from, etc. All of these really do vary wildly by candidate, and it’s easy to see that in reality… No! It’s not all “one big club” funded by the same people. Almost all of these candidates get the vast majority of their funding from many different donors (although of course there’s one who clearly does not - we’ll get into that).

The data below is all filtering for donations since the year after the previous election onwards, to make sure this is representing the most up-to-date support for each candidate. Also, this data is up to date as of July 2025 but will certainly change as the election ramps up.

Find information about where and when to vote on the city elections department website.

Alex Alex (yes, Alex Alex) is a self-described illegal immigrant and recent NYU graduate who has been advocating for bike infrastructure, community gardening, and corporate accountability for packaging waste on his Instagram @alexalex_100fordem for the past year. He is not on the ballot on account of missing the deranged ballot access requirement of 3,000 signatures in three weeks (I’m going to have to make a post on this one). He also is running a remarkable $0 campaign, so there’s not much data for me to map out. He was, however, able to qualify for the Democratic Ward Coalition mayoral debate, where he outlined his philosophy in running for election.

As far as money goes, there’s not much to talk about here. But what can be editorialized is that Alex Alex represents a part of the city which is often completely unrepresented in government. Youth, especially transient college-educated youth, renters, protestors and advocates. People who don’t typically contribute to political campaigns, either due to ignorance or lack of resources. People who are not being effectively outreached to by existing politicians because either they don’t know how to, or more cynically, it’s simpler not to. Should these young people have a stake in the city, given that they may not live there forever?

As one of them, my answer is a resounding yes, but the debate over how to handle this question is the basis of a lot of the resentment and turmoil in city politics. The closest thing the city has to purely economic, private sector actors, they form much of the city’s livelihood - purchasing at the city’s stores, renting up the city’s single-family units, riding the city’s transportation and working for the city’s businesses. It’s hard to argue they shouldn’t have a stake in the city, but their philosophy and perspective are bound to clash with long-term residents. How will this dynamic play out? Young politicians like Alex Alex are bound to play a role.

P.S. He’s hosting a neighborhood cleanup this weekend August 9th and 10th in Franklin Park.

Bob Cappucci is a devout Catholic, retired Boston police officer, and perennial Boston candidate. He has been on the ballot for Mayor of Boston twice now. In 2017, he earned 6% of the vote. In 2021, just 1%. But Bob is a persistent man. The only money he’s amassed for his campaign? $12,675 of his own money. I didn’t include any graphs here because again, there’s not much to analyze.

Even though I don’t agree with much of his politics, I have to admire his lifestyle. At 80 years old, he insists that he still goes to the gym every day, and honestly I believe it. I met him standing outside a Whole Foods collecting signatures, and he had to be one of the fittest octogenarians I’ve ever met. He’s certainly the most conservative candidate in the race, but also decidedly anti-establishment - his only funding has come from himself, and most of that was spent on buying signatures (that’s right, you can buy signatures to get on the ballot! Did I mention I have to make a stack post about this?). I have some amount of empathy for old conservatives (otherwise I couldn’t get along with my family), so much so that I might genuinely consider voting for this man over Josh Kraft, in the astronomically unlikely scenario that they end up in the general together.

Check out his campaign website if you’re interested.

Domingos DaRosa is another perennial Boston candidate and community activist. He ran for city council at large in 2017, 2019, and 2021, and now he’s back running for mayor. I had the pleasure of speaking with him at a community meeting a few weeks ago about the issues facing the city and our democracy. He’s the kind of guy who’s well-known, well-spoken, and well-regarded in the community but unfortunately has no major funding backing him, “eschewing funds in his long-shot mayoral challenge.”

In 2017, he earned 4.38% of the vote in an 8 person race but in 2019 and 2021 failed to advance from the preliminary to the general election. In this race, his only hope to reach the general is siphoning enough support from Kraft supporters, since it looks like Wu is reaching the general regardless. However, given the millions of dollars being poured into Super PACs in this election, it’s going to be an uphill battle.

However, DaRosa has managed to collect enough donations so far to put them on a map.

You can see that DaRosa’s support is strongest in the Black and Hispanic cores of the city in Roxbury and Dorchester, which implies that DaRosa represents a distinct interest in the city from Kraft and Wu. His areas of greatest support don’t overlap at all with theirs. Here we see the weakness of a non-ranked choice system fully exposed, as no matter how the preliminary goes down, one part of the city will be forced to choose between two options that don’t really represent them.

Josh Kraft, famous for being son of Robert Kraft (owner of the New England Patriots), and locally recognized for his charity work with the Boys & Girls Club in Boston. His argument for becoming mayor is a little muddled, but a central theme is that he would “hear the community” more than Wu has. He’s also argued he’ll be able to convince his wealthy friends to use their wealth to benefit the city when Trump attacks, which sounds an awful lot like selling out the city. As for policies, he would remove bus and bike lanes… that’s about it.

The perfect storm of conflicts of interest, his mayoral campaign feels like little more than an coup of the city government for private interests and a reflection of the chaos currently happening in Washington. His father is a major Trump donor. But let’s see what his pockets of support look like.

This, of course, includes the $2 million donation from Josh Kraft to himself, which he made from his new address in the North End - a microcosm of the questions surrounding his entire campaign. Should anyone from the suburbs be allowed to buy a condo in Boston and run for mayor? Are his donations to the Boys and Girls club enough to grant him credibility as a community organizer? Can any billionaire’s child truly relate to the problems of working class Americans? This author thinks the answer to all these questions is no. But ultimately that’s going to be up to you to decide.

Kraft’s support is greatest, of course, in Back Bay and South Boston, where many of the wealthiest, whitest and most conservative in Boston reside. Perhaps he’s trying to make up for this by surrounding (shielding) himself with a colorful campaign staff, and spreading out his own donations to include a variety of colorful candidates. Whether this strategy will pay off, or whether it will be seen through, is hardly a matter of debate, according to recent polling.

Mayor Wu, oh, Mayor Wu. What would we do without you? …is the question Bostonians are faced with this fall.

Maybe the second or third most recognizable mayor in the country, and certainly among the most popular, she’s looking to reinforce her message and continue the “pragmatically progressive” policies enacted during her first term. Already endorsed by half the politicians in Boston, Wu - despite being boasted and derided as a progressive - has turned out to be a quite middle-of-the-road politician when it comes to Boston politics.

Her firm challenge to the President’s attacks on the city’s immigrants has garnered her national adoration, and with her presence and prestige it wouldn’t be surprising to see her angling for national office come 2028. Her administration’s rezoning efforts have pressed forward aggressively, despite the fears of various community “zoning experts.” And many of her agenda items and budget proposals have been greased through the city council by her positive relationships there (this could be seen as a pro or a con I guess).

However, lately she’s been walking back bus and bike lanes left and right, and has faced criticisms that her administration has been poor at community input on projects such as the Blue Hill Ave bus lane and White stadium redesign. Unfortunately, discerning how much of this is valid criticism and how much is manufactured outrage of the campaign cycle is hard to pick apart without the protection of a hazmat suit and the delicacy of a pair of tweezers. The sheer mass of thinkpieces and stinkpieces have been reaching a crescendo over the past few months, and sifting through them all is such a monumental task that I don’t think I’m personally ever going to do it. Just Google “Michelle Wu” and read the news.

Her strongest districts are the progressive regions of Jamaica Plain and Roslindale, her own neighborhood. She also earns the strong support of the South End and Back Bay, earning a significant portion of the more poor-friendly wealthy living there. However, she lags behind in her donations from Hyde Park, Roxbury and Mattapan in a way that I don’t think can be simply handwaved by a general lack of political enthusiasm. Wu is going to have to grapple with the fact that she’s leaking (or perhaps never had all that much) enthusiasm in the most Black and Hispanic neighborhoods in Boston.

Omitting Alex and Cappucci due to a lack of data, we can take a quick look at how all of the candidates stack up. Since January 2022, DaRosa and Wu have received 60 and 23,605 donations respectively. Kraft only opened his OCPF account last year, but he has received 1,931 donations since then.

Kraft’s mean, median and mode (definitions here1) dwarf the others. In fact, the mean is over the $1,000 individual annual campaign donation limit. This is because the data is heavily skewed by Kraft’s own $2 million donation. He’s not the only candidate to contribute to his own campaign - DaRosa also contributed $250 of his own money to his campaign. But Kraft’s donation puts his campaign firmly in the realm of “billionaire self-funded.” As far back as the OCPF records go, no mayoral candidate has spent millions of dollars on their own campaign.

Now, if you say, “that’s just fine, I plan to vote for him anyway,” then maybe you’ll agree we should just do away with democratic government altogether and simply let the “invisible hand” rule over us. After all, if you’re good at running a business, you must be good at running a government.

What I’ve also heard is that Josh’s “love for the community” is the sole motive behind his campaign. This may explain why he’s frittering away so much of his family’s money, but not why his median donation is still $500, fully ten times as much as DaRosa and Wu, and mode donation is $1,000, the maximum allowable donation. I suppose all these wealthy donors must be very on board with Josh’s vague notions to benefit the underserved members of the community.

As far as DaRosa and Wu’s data goes, it’s harder to make some firm statements about the two, but since Wu’s mean donation rises above DaRosa’s, we should expect to see that DaRosa’s distribution of donations is more centralized, that is, more people donated closer to the average donation for DaRosa than for Wu. In fact, why don’t we just look at a histogram of the donations for all these candidates?

Josh’s data looks a little strange - there’s a few donations higher than $1,000 and a handful of contributions lower than $0. These reflect donors who attempted to give more than $1,000 directly to Josh and then were refunded, or whose donations were refunded for some other reason. I have left this data in for purity and transparency’s sake, as they are included in my other charts as well (and since the number of these refunds is so small they barely nudge the data).

There are a handful of factors that contribute to these charts, two notably being the wealth of the donors and their enthusiasm for the campaign. It’s theoretically possible that a more enthusiastic impoverished donor might donate more to a campaign than a less enthusiastic wealthy donor. It’s hard though to see why a multimillionaire or billionaire would donate five bucks to a campaign as opposed to donating nothing.

We can see that my assumption about the distribution of Wu and DaRosa’s data is confirmed. Wu’s data peaks with very small donations but has a second peak with large ones, with a significant portion of her donations coming from the $500-$1,000 crowd. Which makes sense when you consider that Wu is likely hosting more big-dollar fundraising events than DaRosa. In fact, even though only a couple thousand come from the $1,000 donations, she received more money from those than from the 14,000 donations which were $100 or less. When money is amongst the most important factors in an election, currying favor with the well-to-do can pay off big.

An effect that may contribute to the variance of the charts and the somewhat smoothness of DaRosa’s is the differing layouts and amounts highlighted on the campaigns’ donation websites. Kraft offers options ranging from $25 to $1,000, Wu only up to $100, and DaRosa offers no default options at all.

These numbers could also somewhat encourage or discourage smaller donations in general. A Kraft supporter may be thinking to donate five bucks, go to the campaign website and see the options and figure their donation won’t actually make a meaningful difference, then sour on the idea of donating at all. Whether these websites themselves have had an impact on the distribution of donations is hard to say, but they are likely intentionally set up with these options to be geared towards the most common donor buckets.

We can also take a look at the percent of each’s funding and donations from each location.

The distinction between slices of donations - the number of individual donations made - and slices of funding - the total amount of those donations - may seem arbitrary, but depending on the size of the donations can make a huge difference in how much the campaign will care about donations from each location. For example, look at the difference between Kraft’s funding percentage from Boston and donation percentage from Boston. Kraft appears to be receiving many of his high amount donations from within Boston, which matches up with (if you scroll all the way back up) his most popular neighborhood being the wealthy Back Bay. (Note that Kraft’s donation is included.)

The distinction is also a tipping point in Wu’s case, with the slim majority of her donations coming from Boston, but the majority of her funding coming from outside the city. Wu is therefore incentivized to curry favor with suburbanites over Boston residents, at least in terms of the funding she receives from both groups. Whether this crops up in her past and future actions as mayor is unclear to me, but is worth looking out for. I started this post by asking whether recent Boston immigrants should have a say in city politics. Should people who don’t live in Boston have a say?

Being able to effectively fund a campaign is paramount in winning an election. Nobody who doesn’t hold a fat wad of bills is going to hold office. The reality of our political process is that there is an “election before the election,” which can only be participated in by those with money and influence. Influence can be difficult to quantify - it could constitute preferential treatment by media and the press, favor with powerful unions or PACs, or relationships with existing elected officials leading to endorsements.

Money, on the other hand, is quantifiable, trackable, and plottable. Its flow can be traced through the engine of the political machine, and those it influences and favors can be picked out from the crowd. A law does not have a price tag. But an effective lobbyist knows how to make their clients’ money work. And politicians aren’t oblivious to the fact that they would be sunk if they ceased to do as their donors pleased.

If you’re interested in delving deeper into the weeds with me, please subscribe to my Substack or my Instagram @kelsoforcitycouncil. I plan on creating another post or two attempting to make sense of some of the city council races. Also, leave a comment below and I will be happy to respond and discuss your own insights into the data I’ve collected here. I am not a native Bostonian and I’m always pleased to learn more about the local historical context behind these candidates and political trends.

-Ryan

Okay, here’s a couple more charts. These are maybe better than those I included in the main text of the article but I don’t have the energy to restructure everything to include them. Onwards and upwards.