I posted recently about strategies to result in a 6th place finish for Jack Connolly, and I think there is one.
Last time Connolly got votes from just shy of 55% of voters. This was good for fifth place, a bit over 7% behind the fourth place candidate. Let's imagine he gets 55% again. (Each voter gets four votes.)
Let's also imagine that a fair fraction of Connolly voters want him to win and are therefore more likely to vote for last year's top three, which were Mary Jo Rossetti with 81%, Stephanie Hirsch with 69%, and Bill White with 64%. These are the candidates who will come ahead of Connolly anyway, who have been around Somerville forever, aren't firebreathing progressives, are white, and got lots of crossover with Connolly last time. Plus a vote for Hirsch is insurance; if Connolly doesn't get elected and she quits, he has a second chance.
If votes were independent you'd expect 34% of voters to vote for both Connolly and Mbah, based on last year's numbers. But Connolly voters are not super likely to vote for Will Mbah or Kristen Strezo because those are the candidates who might beat out Connolly, and also because they're the most opposed to Connolly's politics. So the number has to be less. It can't be too much less, though: last time at least 17% of voters voted for both Connolly and Mbah, as their totals added up to 117%. Let's imagine that somewhere between 20 and 25 percent of voters will vote Connolly-Mbah, and between 10 and 15 percent will vote Connolly-Streza.
Allocating the remaining Connolly votes more or less proportionally, and leaving a few for the two fringe candidates or for undervotes, let's guess that 40% of voters will vote Connolly-Rossetti, 35% Connolly-Hirsch, and 30% Connolly-White.
The remaining 45% of voters are just enough to get Streza ahead of Connolly if we all vote for her. We then want to allocate our other three votes among Rossetti, Hirsch, White, and Mbah so that each has a comfortable margin. If we do this optimally we can get each of them a 10% margin. We do this by all voting for Mbah, 77% of us voting for White, 66% of us voting for Hirsch, and 55% of us voting for Rossetti.
In fact not every anti-Connolly voter will be following this playbook. Probably Hirsch will be underrepresented and Rossetti will be overrepresented.
So my recommendation is to roll D6. If it comes up 1, leave White off your ballot. If 2, leave off Hirsch. 3 or higher, leave off Rossetti.
If you don't like playing dice, this rounds off to endorsements for:
Stephanie Hirsch
Will Mbah
Kristen Strezo
Bill White
I don't expect Strezo to make it to 4th place. In fact even playing by this strategy she might not come ahead of Connolly for 5th place either. But it's super unlikely that this leaves you in the position that there's someone you could have voted for who would have beat Connolly if you had, and almost as unlikely that your vote put Streza on the council over an incumbent either.