Ethan Wolin

The Republican president was holding up millions of dollars of funding that Congress had allotted to aid cities. The Democratic mayor of New Haven sued to secure the money for local programs, putting the Elm City at the forefront of an effort to stop the president from making unilateral spending cuts.

It was early in 1986, and Mayor Biagio DiLieto confronted delays in housing funds he was expecting to flow to the city from the federal government. President Ronald Reagan, trying to curb government spending, had deferred paying out $8 billion to cities — including $638,000 due to New Haven that year from a Community Development Block Grant, as well as housing subsidies for nearly six thousand city residents.

“New Haven depends on these programs for its poor and elderly and for its revitalization efforts,” DiLieto said in a press release after the city filed a complaint that February in federal district court in Washington, D.C.

The city won the case on summary judgment and won an appeal. Now, 39 years after New Haven took the Reagan administration to court, Mayor Justin Elicker signed the city on as a plaintiff in two lawsuits against the Trump administration during its first two months.

The first recent lawsuit takes on President Donald Trump’s crackdown on so-called sanctuary cities that refuse to bolster immigration enforcement. The second one challenges his moves to freeze environmental grants — and the complaint, filed this month on behalf of six cities and eleven organizations, cites the 1987 appellate ruling that reaffirmed New Haven’s victory over Reagan. For New Haven, it’s a precedent twice over.

Graham Provost, an attorney with the nonprofit Public Rights Project that helped assemble the new lawsuit, said in a statement provided by the group’s spokesperson that the complaint’s authors “chose which cases to cite based on their legal relevance. And it is an added benefit to point to a situation involving one of our plaintiff cities.”

The legal issue in the Reagan administration’s 1986 appeal concerned the 1974 Impoundment Control Act, which restricts the president’s authority to withhold or delay congressional appropriations. In particular, after the Supreme Court had invalidated the law’s one-house legislative veto power over presidential spending deferrals, could the president still defer spending by himself?

No, the district and circuit courts concluded. At least not for the president’s policy reasons, as opposed to routine “programmatic deferrals” in the course of executing a law, according to the unanimous three-judge appellate panel — which included Judge Robert Bork, just six months before Reagan would announce his ultimately failed nomination to the Supreme Court.

It’s that technical distinction between policy and programmatic spending delays, outlined in the 1987 D.C. Circuit ruling in City of New Haven v. United States of America, that comes up briefly in New Haven’s latest joint lawsuit against the Trump administration. But in both cases, the city emphasized the urgent real-world implications of a dispute about the separation of powers.

“Much more is at stake here than the political machinations between two branches of government operating at either end of Pennsylvania Avenue,” New Haven argued in a 1986 filing to the district court.

Neil Proto, a New Haven native and former Justice Department lawyer who represented New Haven in the housing funds lawsuit, told the News that it was part of a broader push by DiLieto to revive the city’s urban center and housing options. DiLieto was also waging a multifront legal battle against a proposed shopping mall in North Haven that he feared would gut his city’s downtown.

Where Reagan pulled back on some spending, Trump has taken a more radical approach to disrupting the federal government, Proto said. Trump has signed a torrent of executive orders, several of them threatening funding streams to cities. The Environmental Protection Agency has put in limbo over $30 million in grant money promised to New Haven, some of which would normally be paid as reimbursements for projects already underway.

“We are doing what we can in New Haven to confront this climate crisis,” Elicker said at a March 20 press conference about the environmental funding lawsuit. “Unfortunately, we have a president of the United States right now that is doing just the opposite and illegally stymieing and setting up roadblocks to our nation’s ability to address climate change.”

There are other differences between the 1986 and 2025 lawsuits, besides the presidential actions at issue.

Elicker has made a wide-ranging push to counter the Trump administration, through municipal policies and through messaging frequently focused on championing progressive “values.” He struck a defiant tone in his State of the City address last month, describing New Haven’s multicultural character as a rebuttal to Trump’s vision for the country.

DiLieto was less liberal and less ideologically driven, according to Steve Mednick, a lawyer who served on the Board of Aldermen, now called the Board of Alders, representing Westville’s Ward 26 from 1982 to 1991.

“He wasn’t part of the progressive movement. He was pretty middle of the road,” he said about DiLieto, who was New Haven’s police chief before running for mayor. The desire to sue the Reagan administration, Mednick said, “came down to the fact that we were going to lose substantial sums of money.”

New Haven is receiving free legal support for the two current lawsuits from Public Rights Project, the California-based organization that is mobilizing municipalities across the country to challenge Trump policies.

San Francisco and Santa Clara County, California, spearheaded the sanctuary city lawsuit, which had three other plaintiffs when it was filed in California in February and later added 11 more plaintiffs — all of them cities or counties. The Southern Environmental Law Center joined with Public Rights Project to assemble the climate funding lawsuit, filed in South Carolina. Elicker is the only New England mayor to participate in either lawsuit, at a time when many local leaders are lying low to stay out of Trump’s crosshairs.

In the clash with the Reagan administration, New Haven stood out even more. As the National League of Cities, or the NLC, looked for cities to join forces against the housing money delays, DiLieto had another idea, Proto recalled.

“He didn’t want to just piggyback on top of a dozen other cities. He wanted to be first,” said Proto, who had been a political strategist for DiLieto. “That was one of my purposes, to ensure that that happened, and we did” — by one day.

New Haven submitted its complaint on Wednesday, Feb. 19, 1986. On Feb. 20 came a lawsuit on the same subject from a bevy of plaintiffs, including the NLC and four members of the House of Representatives — among them New Haven’s Rep. Bruce Morrison and New York’s Rep. Chuck Schumer, now the Senate minority leader. New Haven moved to consolidate the cases the next month, retaining its pride of place in the case name.

David C. Vladeck, the lead lawyer for the NLC and other plaintiffs, later wrote that he had “serious reservations about the City’s decision to file its own case.”

That comment came in a letter to the editor of the New Haven Independent — a weekly newspaper that stopped printing in 1990, succeeded since 2005 by a news website of the same name — in which Vladeck defended Proto’s integrity from the newspaper’s suggestion that he had milked the case for profit while playing a redundant role. The original Independent story, headlined “Case pays off for Proto,” reported that the city paid Proto $10,000.

No doubt, DiLieto cared about New Haven’s prominence in the proceedings. In a memo to the mayor after the district court argument — preserved along with other documents from the case in Proto’s papers at his alma mater, Southern Connecticut State University — Proto reported that he had let the NLC attorney speak first. “As I indicated before, however, I have retained the option of going first in the Court of Appeals, if necessary,” he wrote.

In the end, Proto said, he stood up first at the appellate oral argument to say that New Haven would adopt Vladeck’s arguments, before ceding the podium to him.

By the time the decision came down from the D.C. Circuit on Jan. 20, 1987, Proto had already been officially commended by the Board of Aldermen for his “tremendous efforts” toward the lower-court triumph. And, the prior July, the contested funds had already been distributed after Congress intervened with a supplemental appropriations bill.

DiLieto stepped down in 1989 after a decade as mayor, and died in 1999.