Examining Milford Municipal Politics Part 1: Allegations Of Selectman Misconduct And Cover-Up Unresolved, Questions Of Corruption Remain

Nearly a year after town Selectman William Kingkade's alleged drunk driving incident and the ousting of popular Police Chief O'Loughlin, residents search for answers in murky waters.

Milford has been on our radar a lot lately. Between the bootleg “homeless shelter” that town officials have turned a blind eye to, despite being an obvious sanitation and fire hazard nightmare run by a habitual liar and lunatic who rips off vulnerable homeless families for her own benefit; the former resident who spends her time smoking rolled cigarettes and blunts from Maine while calling in kidnapping scares; and the court circus that just occurred today, there’s just a lot to talk about in Milford these days. What kind of town allows this sort of tomfoolery to go on?  To answer that, let’s revisit a blog published last September, about an incident which sparked public outrage and has since morphed into a chain of events that is going to keep us looking at Milford for quite some time at this rate. Anyone have a spare room for us in Milford while we stick around for a while?

No. Not you. Anyone else? Because this story gets pretty involved, so we may be booking an extended stay.

We have obtained so much information at this point that one blog is not going to do any justice here. And we first have to walk back, all the way back to October 2018 and a little story we wrote about a saucy little Selectman, his pickup truck and a pole. So strap on…..your helmets folks, because it might get a little wild. This will be Part One of a series of blogs, and I want to take you back on a trip down memory lane in TB-ville.

Remember Milford Selectman William Kingkade, Jr?

He’s the genius whose two-ton pickup truck was violently accosted by an out-of-control telephone poll that jumped out at him at 12:48am while he was totally stone-cold sober, you guys. We covered it in October 2018, and you can catch up by clicking the link here, but I’ll give you a brief refresher course. Billy and his Masshealth glasses were “guest bartending” an event at a local bar on the evening of September 23, 2018. He was slated to arrive at 8pm.

Later that night, at 12:48am (technically September 24th), the rouge utility pole leap into action and in front of Kingkade’s pickup truck, totaled it, and Kingkade took off. Definitely sober, of course.


He pinky-swears. Don’t listen to the purported eye witness testimony….


….Just trust the guy at the bar who played chicken with a telephone pole at 1am and fled the scene in his smashed up truck on three wheels.


If this were you, or me, we’d be one active driver’s license lighter in the wallet and in front of a judge faster than you can say, “I only had one beer, two hours ago.” But Billy is a town official, and town officials often make useful friends, so allegedly a detective Robert Pavia helped cover all this up. We really can’t confirm or deny that allegation at this juncture, nor could we a year ago….but there’s enough suggestive evidence to at least justify a closer look. I’ll defer to our previous blog on that one in the interest of keeping this concise.

Cover-up allegations, questionable dispatch audio, and pictures of smashed-up debris allegedly in the back of the detective’s own truck? That should trigger an internal investigation into the actions of the police department employees in question, right? Nope, wrong; more on that in the later blogs. Let’s just note that as of today, no internal investigation has been launched, despite public allegations of a cover-up with some compelling evidence behind them, that could easily be either substantiated and dealt with, or put to rest, by means of an impartial investigation.

Prior to Selectman Kingkade’s early morning pole ride, he came under heavy scrutiny after he and one other Selectmen, William Buckley, voted to not renew the well-liked and highly regarded Chief of Milford Police, Tom O’Loughlin, despite the entire town’s well-documented and vocal objections.


Now retired, former Milford Police Chief Tom O’Loughlin began negotiations for a final three year contract with the Town of Milford and the Board of Goons during two Executive Sessions one in October 2017 and the other in January 2018. Executive session is just a fancy way of saying; they don’t want the public to know what they’re discussing behind closed doors, because it’s their club and you can’t join. According to court records, prior to the discussions which ensued behind closed doors, the selectmen told the Milford Town Administrator Richard Villani and the Administrative Assistant to the Chief of Police to leave the room against O’ Loughlin’s wishes.And since this this is a “personnel matter”, apparently, or at least according to town attorney Chris Brown, we don’t get to know, and that is that.

That was that,  until they realized that O’ Loughlin took “contemporaneous” hand written notes at the first two meetings. The easy way to counter and dispel such notes, one would think, would be to release the minutes for the meeting in question, but that’s apparently not going to happen as long as Kingkade, Buckley and Walsh have anything to do with it.



That troubled resident was a man named Dominick Cristino, who was indicted on criminal stalking charges for his outspoken criticism and activities against O’ Loughlin. In all fairness, his conviction was later vacated after an Appeals Court deemed that his public statements (which were  perceived as threats at the time) were protected free speech as O’ Loughlin was  a public official. Caselaw notwithstanding, this guy also appears to be kind of insane.

Just look at him.

And he was definitely a little over-the-top in his efforts to injure O’Loughlin.




and over,


and over again.


Whoever Steve is, I’m pretty sure he can attest to the point that Dominick is a loon. Presumably the town of Upton can, too. 

The town investigated these allegations and an official letter from the then town attorney, Gerald Moody, was released to the resident stating,

“The above email complaints were investigated and found to be baseless.”

O’ Loughlin had negotiated a contract renewal in 2015 with the Board of Selectmen which ironically was around the same time allegations were being launched against him, but the board renewed then without hesitation. Why? Because the board of Selectman echoed the conclusion of the town attorney,  deeming the allegations baseless and leveled with ulterior motives behind them.

Case closed. Until 3 years later.


Apparently, you can drunkenly hit a telephone pole at 1am and flee the scene and keep your position in the town of Milford, no problem. You can’t have any unsubstantiated allegations made against you by an angry, fat Cheech who writes on fences for fun and also enjoys mind-altering substances from the comfort of his car, though. Those will cost you your job, three years after you’re cleared for it. Makes perfect sense. And the opinion of the residents you’re supposed to be serving does not matter at all.

On October 22, 2018, the Milford Board of Selectmen held a regular meeting in their board room which was nearly filled to capacity with several residents speaking in support of the Chief and asking that they re-enter negotiations and allow the Chief to remain for three more years, which would bring O’ Loughlin to the mandatory retirement age of 65. The then-Chairman of the Board, Selectman Mike Walsh, motioned to rescind the vote to not renew the O’ Loughlin’s contract and re-enter negotiations which received applause from the residents, But that was quickly squashed by Selectman Buckley, who accused the Chairman of “theatrics”. Both Buckley and Kingkade declined to second the motion, instead opting for more secret closed-door discussions.

The Board later responded after their secret squirrel meeting with a warm and fuzzy announcement that by all appearances removed them as the responsible party for the lack of negotiating, they stated that they would re-enter into negotiations pending a response from O’ Loughlin to a March 26, 2018 “personnel memo” addressed to him.

In Part 2 of this blog, we’ll get in to this memo more, and the suspicious circumstances surrounding it. We’ll also look at the question – why axe the Chief amidst such vehement public outcry? What do Kingkade and Buckley have to gain?







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