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A Massachusetts police chief says selectmen violated his rights. Now he’s suing.

“Certainly he’s earned the right, I think, to end his career on his own terms.”

Milford Town Hall as seen from the town's Main Street. Christopher Gavin/Boston.com Staff

Since 2002, Milford Police Chief Thomas O’Loughlin has renewed his contract every three years with the town’s Board of Selectmen.

Except last year.

In early spring, negotiations stalled. Months later, he was notified his employment with the town would come to an end when their current agreement expires this June.

Now O’Loughlin, a 41-year law enforcement veteran and a 30-plus-year career chief in communities across Greater Boston, is in the midst of an unusual lawsuit that pits the popular chief against Milford’s top officials.

“He’s never been brought in for any type of discipline of any kind,” Ernest Horn, his attorney, recently told Boston.com. “He has on two separate occasions received a unanimous vote of support from the police union, which is sort of unheard of. He is beloved by the community.”

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Filed in Worcester Superior Court in November, O’Loughlin’s complaint alleges he was “unlawfully and unjustifiably removed from his appointed position” by a 2-1 vote by selectmen two months earlier.

The suit specifically names Selectmen William Kingkade Jr. and Bill Buckley, who O’Loughlin’s attorney alleges opted to terminate O’Loughlin’s employment agreement knowing they didn’t have the authority to do so.

The pair also backed the decision to form a search committee for a new chief to replace O’Loughlin, once chief in Wellesley and Wayland and at the helm of the MBTA’s police force.

“Their actions were willful, intentional, malicious and intended to damage O’Loughlin’s reputation in the community and his professional reputation,” wrote Horn, who believes the board acted on a deliberate attempt to oust O’Loughlin to advance the careers of others within the department. “Every day that passes with the refusal of the Board of Selectmen to rescind their unlawful vote or non-renewal and termination … increases the damage to his good name.”

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The lawsuit seeks that the court declare the selectmen’s vote null and void while issuing O’Loughlin financial compensation for damages.

But officials contend the town and selectmen acted within their rights — as laid out in the contract — and based off concern regarding O’Loughlin’s alleged inappropriate behavior on the job.

Christopher Brown, special counsel for the Town of Milford, said O’Loughlin’s argument is “an incorrect, and frankly, absurd reading of the contract,” according to an email to a reporter provided in court documents.

“His arguments repeatedly refer to the Board’s action as a ‘termination’ or a ‘removal’ in an obvious attempt to sensationalize the Board’s action despite the fact he remains employed by the Town through June 2019,” defense attorneys wrote in one filing. “The Board decided not to reappoint the Chief in accordance with the plain language of the contract.”

Earlier this month, a judge ruled against offering a preliminary injunction to O’Loughlin — an effort Horn has said would have blocked the town from searching for a new police chief as the court examines the case.

Brown, in an interview, said the decision means it’s likely the case will not continue.

But Horn said O’Loughlin isn’t backing down.

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Milford Police Chief Thomas O’Loughlin as seen in an August 2002 file photo, one month after he was hired.

‘I think there’s a few people inside the department that want to move up’

O’Loughlin met with selectmen to renegotiate his contract in closed-door meetings during late 2017 and early last year, according to court filings. The three-year agreement being discussed would have carried O’Loughlin through 2021 when he turns 65, the state’s mandatory retirement age.

A memo filed by Brown and attorney Seth Barnett, who is representing Kingkade and Buckley, states that O’Loughlin and selectmen could not come to an agreement partially because of issues the board had surrounding notes O’Loughlin took of two of their negotiation meetings.

Those notes formed the basis of an open meeting law complaint filed by a Milford police sergeant against the board last March, which claimed selectmen had instead violated his own rights.

Selectmen, in a letter to O’Loughlin dated March 26, 2018, outlined their concerns regarding the release of the notes, calling O’Loughlin’s account of the meetings “patently false.” Additionally, they asserted that the conversation centered on allegations of O’Loughlin drinking during the work day with subordinates.

Those accusations, cited by officials, came to light in recent years from a former town resident — an outspoken critic of O’Loughlin who was initially sentenced to up to two-and-a-half years in state prison for stalking him but later had the conviction vacated in 2017.

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At the time the allegations were brought to the board in 2015, Town Hall officials called them “baseless” and “malicious.”

According to Brown, similar allegations have since been reported to officials by other people, which ultimately led the board to its decision last fall. Brown said he did not know who the accusers were.

In September, selectmen opted not to renew O’Loughlin’s contract after not receiving a response to their March letter. He was offered a 3 percent raise for the rest of his employment — totaling an annual salary of $135,404, according to paperwork submitted by Brown and Barnett.

But selectmen never asked for a response, including even during two meetings with O’Loughlin after the letter was sent, according to Horn.

“The letter is pretty much a statement of what (the selectmen) believe,” said Horn, who argues it should never have been made public because of the personal nature of its contents.

Ultimately, O’Loughlin responded to the letter in October with a letter of his own, which states that Brown was unable to provide Horn specifics on new allegations against him.

“Given that there is no reference within the Board of Selectmen letter … to a specific event in which these alleged circumstances occurred, I can only respond by informing the Board of my intent to be particularly vigilant in clarifying any misperceptions or misunderstandings as it relates to my personal, rather than professional, presence and capacity as an invitee at future social gatherings and events,” O’Loughlin wrote.

Horn contends the board is following through on an attempt to undermine O’Loughlin and reorganize department leadership.

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“What some of this boils down to is that I think there’s a few people inside the department that want to move up and they have some friendships with members of the Board of Selectmen, in fact one of them is the brother of one of the selectmen,” he said.

Asked whether he could substantiate those claims, Horn said he feels his point will be made clear in testimony, phone records, and emails once the case heads to discovery, adding he has a “gut feeling” about it.

“It’s rather sad that people he has done so much for would try to undermine him with this,” he added.

In court documents, defense attorneys for the town and selectmen wrote O’Loughlin did eventually respond to the March letter in October, but “hid behind a canned response playing coy,” focusing on the source of the drinking allegations above other points outlined by officials.

“The Chief’s actual response failed to live up to these expectations, dismissing some of the Board’s concerns raised in the Board’s correspondence in face-to-face meetings with the Chief in executive session,” one filing reads. “Not surprisingly his response (or lack thereof) failed to convince the Board to reconsider its prior decision not to renew his contract.”

Both attorneys wrote that rumors raised by Horn about members of the department were “inaccurate and speculative.”

Brown told Boston.com he never heard those rumors. Horn mentioned them once in a court hearing, but never wrote about them in court files, Brown said.

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“Obviously the town can look at internal candidates (for the position), too,” he added.

Brown and Barnett, in court filings, also dismissed the notion that the March letter — including the allegations that O’Loughlin drank on the job — could be considered part of a personnel file or of a personal nature.

“Allegations of that nature, made about one of the Town’s senior management officials, are clearly a matter of public concern and the Chief’s privacy interests, to the extent that they are invoked here at all, have to be balanced against the public interest,” they wrote.

‘Nothing in the contract requires that’

Under the terms of the employment contract, selectmen and O’Loughlin had to agree to enter negotiations, which the two parties did in 2017, according to Horn. That notice must be given at least six months before the current terms of the contract expire.

Should the parties decide to renegotiate, “the terms and conditions of this Agreement shall remain in full force until a successor agreement is executed,” according to a copy obtained by Boston.com.

The contract does not explicitly say what happens in the event that the two parties don’t broker a deal.

Horn argues that since both O’Loughlin and the selectmen agreed to enter negotiations, they essentially opted for a renewal of the contract.

He said the board’s decision not to reappoint O’Loughlin based on his lack of response to its letter should be considered a punitive action.

“That’s discipline,” Horn said. “He has an absolute right to due process.”

Brown and Barnett have disputed what they refer to as the “evergreen clause” — the belief that the contract’s language means the board was obligated to reappoint O’Loughlin once the two parties agreed to start the negotiation process.

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“Even if the Board started to renegotiate with the Chief, that did not bind the Board to reach agreement with him. Nothing in the contract requires that,” the attorneys wrote. “To turn the examples offered by Attorney Horn at the hearing around, if the Chief demanded an annual salary of $1 million dollars, and was inflexible on that point, it cannot reasonably be said that the Board would have been obligated to continue negotiations. Furthermore, based on the Chief’s flawed logic, he would be precluded from changing his mind during such negotiations to take a job elsewhere or simply retire.”

Selectmen can vote to terminate a contract based upon “inefficiency, incapacity, conduct unbecoming or insubordination,” but they must notify the chief 30 days before they intend to make a vote, the existing contract states. The chief would also be entitled to a hearing — public or private, his choice — before the board, where he could call witnesses and be represented by an attorney.

Brown and Barnett have said the board never terminated the agreement, but rather chose not to reappoint the chief.

“Really, I think it came down to a matter of contract interpretation,” Brown said in an interview.

This month, Superior Court Justice Gavin Reardon Jr. denied Horn’s motion for a preliminary injunction as the case plays out, essentially siding with the town’s argument.

Reardon wrote it is not clear if the chief would be irreparably harmed if the injunction was denied and if he was, whether it would outweigh any harm to the board if its unable to search for a replacement chief.

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Furthermore, the language of the contract “does not require the board to enter into a successor agreement,” Reardon wrote.

It merely states that the original terms and conditions remain in effect while the parties are renegotiating,” the document reads.

The town’s search for a new police chief can now move forward, and, if the decision stands in court or the lawsuit is dismissed, O’Loughlin’s tenure will come to an end in June.

The Milford Police Department headquarters

‘He’s earned the right … to end his career on his own terms’

As the news of the board’s decision played out in town, O’Loughlin gained many supporters, among them the three former selectmen who hired him, who have signed affidavits vouching for Horn’s interpretation of the contract.

“I think that the chief has always done and continues to do an outstanding job in leading the Milford Police Department,” Brian Murray, sitting state representative for the 10th Worcester District and a former Milford selectman, said in an interview.

Murray, citing his 16 years on the board without issue with O’Loughlin, highlighted that O’Loughlin’s department always operated within its budget and managed high profile crime cases with professionalism.

When he was hired in 2002, O’Loughlin was hurled into a department rife with problems surrounding internal politics.

“The department really was very disorganized and there was really low morale and it was not functioning well at all,” Murray said. “And he turned it around, almost immediately.”

Last week, four additional former selectmen added their voices in a letter — signed by six in total — read aloud by former Selectman John Seaver during the board meeting’s public comment session.

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The group emphasized that it did not want to interfere with executive decisions, but instead wanted to offer their perspective given its collective experience in handling these kinds of matters and urged officials to return to the negotiating table.

“Through independent discussion and review of the facts at hand, it appears that the non-renewal of the police chief’s contract has caused a considerable distraction to the board, to our citizens, and to the Milford Police Department. This climate is detrimental to all involved and it is not in the best interests of the Town of Milford,” Seaver said. “Although we are reluctant to get involved, as former selectmen we have a deep care and concern for our town. We recognize and appreciate that the longer that this turmoil remains, the more problematic it becomes to find a mutual compromise.”

The former selectmen warned that the dispute could continue to carry over into “multiple lawsuits, investigations, employment matters, and other unforeseen violations” that would burden the town’s finances and attention.

The letter continues:

“By opening negotiations with all parties, there becomes a hope for compromise. Doing so would neither frustrate the process nor create a negative judgment from our citizens. Instead, it achieves a balanced, deliberative approach to a most difficult situation which honors and respects your positions and the views of Milford’s citizens while quelling the divisiveness that has ensued. This reasoned approach serves the board and the citizens of Milford now and in the years to come. Please consider a motion for reconsideration and open the path for compromise. We trust your review and hold hope for a compromise ahead.”

Due to meeting rules, selectmen could not comment on the letter publicly last week, but the board later continued discussions about the formation of a committee to search for O’Loughlin’s replacement.

Across town, signs expressing support for O’Loughlin peppered front yards after the board’s vote last year. On social media, residents expressed confusion and disappointment with the decision.

“Certainly he’s earned the right, I think, to end his career on his own terms,” Murray said.

Confidence on both sides

Brown said the court’s decision on the preliminary injunction motion went beyond providing only what was required to deny it, and instead included important insight on the language of the contract itself.

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“It’s obviously a good decision for us, the decision that came down. … We’ll be hoping to obtain a dismissal of the case in the near future,” he said.

Horn acknowledged the motion for a preliminary injunction had a high burden of proof. But he remains confident additional information collected in discovery will prove instrumental in supporting O’Loughlin’s case.

“If we prevail in this case and they have hired a new chief come July 1, they will effectively be paying two police chiefs because obviously they’ll be dealing with who stays and who goes,” Horn said.

The Superior Court case is also hardly the only avenue O’Loughlin is exploring.

According to Horn, O’Loughlin has filed complaints with the state Attorney General’s office for alleged open meeting law violations and for the unlawful release of personnel records.

Another filing is before the Massachusetts Commission Against Discrimination alleging O’Loughlin was denied reappointment because of his age and a disability.

“We feel very good about the case and very much about getting into discovery,” Horn said. “Because I truly believe when we start … we’re going to get a very clear picture of what’s going on here.”