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The e-mail was sent in April 2017. Boston police had arrested a local immigrant for an undisclosed crime, and a police sergeant wanted to alert his counterparts at US Immigration and Customs Enforcement. The suspect faced deportation, yet there was a chance he could be released before he could be removed from the country.

“This guy is at Nashua St. [jail] and has a detainer. . . . His state case bail was reduced the other day, he may be able to post it,” wrote Boston police Sergeant Detective Gregory D. Gallagher.

And the ICE agents were appreciative, with one of them writing back, “10-4, thanks Greg,” as he laid out plans to apprehend the man.

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Newly released police documents show that Gallagher cooperated regularly with federal immigration authorities, despite a city regulation — called the Trust Act — meant to prevent police involvement in civil immigration matters.

The e-mails from Boston police servers show that Gallagher was actually deputized as an ICE agent, which could be itself a violation of the Trust Act. He filled in as an agent for ICE officers on leave. And he communicated with ICE agents frequently to check on the immigration status of people who initially had been arrested for crimes but who could be subject to civil deportation proceedings.

The exchanges, among hundreds of police documents obtained by the American Civil Liberties Union and shared with the Globe, raise new questions about police compliance with the Trust Act, a symbolic effort to build trust between police and the local immigrant community.

In response to the revelations, Mayor Martin J. Walsh said that Gallagher had been removed Friday from his post as liaison to ICE. The mayor said he is committed to ensuring Boston is welcoming to immigrants and is working to rewrite the Trust Act to spell out what officers can and cannot do.

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“Boston is a city that values and respects immigrants, and we will continue standing by our immigrant community who make positive contributions to our city each and every day,” Walsh said in a statement.

Gallagher had been assigned to be the department’s only liaison with ICE through a partnership former commissioner William Evans signed with homeland security officials in 2014. The agreement was meant to build a partnership between police and federal agents to investigate crimes and homeland security matters. At the same time, though, the city’s Trust Act dissuaded police involvement in immigration matters, which are civil affairs.

Attempts to reach Gallagher to comment Friday were unsuccessful.

The e-mails indicate that in at least some of the cases, the suspects had indeed committed crimes — but Gallagher also involved himself in their deportation for immigration violations.

Laura Rótolo, staff counsel and community advocate for the ACLU of Massachusetts, said the e-mails show a “significant breach of the public trust.”

“BPD officials have repeatedly assured the public and the City Council that they are not interested in acting as ICE agents,” she said. “Yet, for at least a decade, they have had an officer embedded with ICE, working hand-in-hand to deport Bostonians.”

The police department did not immediately respond to a request for comment. In recent City Council hearings, department officials repeatedly have denied cooperating with ICE in matters other than criminal investigations.

But the documents obtained by the ACLU paint a picture of regular interactions between ICE agents and Gallagher, the department’s liaison to a previously unknown ICE task force, on civil matters such as detainer requests.

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In February 2019, Gallagher sent ICE a report of a man who was arrested with a Honduran ID. The agents, in turn, continued the e-mail discussion to secure a formal request to hold the man. “Email to Greg, he will make sure [the detainer] gets to packet,” the agents wrote.

In another case, in March 2019, an ICE agent apparently had faxed a detainer request to a local court, and notified Gallagher. “Happy hunting,” the ICE agent wrote in an e-mail to Gallagher.

City Councilor Josh Zakim, the author of the original 2014 Trust Act, said he could not comment on the specifics of the e-mails, because he had not read them. But he said they appear to conflict with the overall intent of the Trust Act — to prohibit any Boston police involvement in civil immigration proceedings.

“The original Trust Act is quite clear that Boston police officers are prohibited from detaining individuals based on their immigration status,” Zakim said in an interview, saying that city officials, including councilors and the mayor, agreed there are “more important things to work on other than federal civil immigration matters.”

The original language of the Trust Act generally seeks to discourage Boston police cooperation with ICE on immigration matters, though Zakim said the new version would more clearly spell that out.

The ACLU review was sparked by concerns in a high-profile case earlier this year that Boston police notified ICE agents of the whereabouts of a man who was wanted for deportation, and who was ultimately arrested by ICE agents after he went to his worksite at a construction company.

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The disclosure, first reported by WBUR of Boston, was made in a federal court complaint that the US Department of Labor filed in February accusing a South Boston company, Tara Construction, of retaliating against the worker for seeking workers’ compensation for an on-the-job injury by having him deported with the help of Boston police.

The CEO of Tara Construction, Pedro Pirez, had told a police detective that he suspected the employee may have given him a false name: The federal complaint alleges the concern was a pretext to having the employee deported.

Police have said that the worker, Jose Martin Paz Flores, had been under investigation for stealing the identity of another immigrant with a green card, and Gallagher relayed that information to ICE agents.

However, a lawyer for Paz Flores, who fled Honduras 18 years ago, pointed out that he had never been charged with a crime on any matter. He had been wanted by ICE for deportation because he missed an immigration hearing in 2002.

Immigration advocates argued that Boston police broke the spirit of the Trust Act by essentially collaborating in a civil deportation proceeding when no warrant for criminal charges was at play.

Zakim said the recent case, as well as the e-mails, require a closer look at the language of Boston’s own Trust Act, amid what he called the Trump administration’s “hostile” environment toward immigrants. He said other communities, such as the state of California, have explicit directives prohibiting police from sharing immigration information with federal authorities unless ordered, for instance, by a court.

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The new proposal would clearly prohibit police from inquiring about a person’s immigration status, or detaining anyone for immigration matters, or providing information to ICE about an immigrant’s release from city or state custody, or making an arrest based only on an ICE warrant.

“We want to make sure city employees are making sure everyone feels welcome,” Zakim said. “We cannot prohibit federal ICE agents from coming and detaining people. What we can control and are working to continue doing is making sure our own employees, our own authorities, are not doing it.”


Milton J. Valencia can be reached at milton.valencia@globe.com. Follow him on Twitter @miltonvalencia.