On the night Joe Lentol won his first campaign, Richard Nixon was storming to re-election as president of the United States. John Lindsay was still mayor of New York City. A young real estate developer named Donald Trump had been recently named the head of his family business, the Trump Organization.

New York and the United States have, in many ways, been radically reshaped over the last half century, but the Williamsburg and Greenpoint neighborhoods of Brooklyn have known only one State Assemblymember. Since 1972, Lentol has held the seat continuously, rarely facing a serious challenge. His last highly competitive race was his first one: then a 29-year-old attorney, Lentol narrowly edged out a Republican by just a few hundred votes.

In this June's primary, almost 48 years after that first race, Lentol will be forced to compete again. He will face a local activist named Emily Gallagher who was won the support of some reform Democrats in the area, hoping to pull off an Alexandria Ocasio-Cortez-like upset against an incumbent who may be tougher to dislodge than Joe Crowley.

"Just running this race, just having an election is really important,” Gallagher told Gothamist. “Our democracy in New York is very broken.”

Williamsburg and Greenpoint have changed drastically since Lentol first took office. In the 1970s, they were working class neighborhoods, home to a large contingent of Italian, Polish, Jewish, and Latino immigrants. In the 1990s, Williamsburg was a hub for artists and upwardly mobile new arrivals. By the late 2000s, the area had rapidly gentrified, with a Michael Bloomberg-backed rezoning triggering the development of luxury condominiums along the waterfront. The working and middle classes have largely been priced out.

The influx of new residents has pushed the area’s politics further left. Bernie Sanders, while losing Brooklyn, defeated Hillary Clinton handily in Lentol’s district. Cynthia Nixon beat Governor Andrew Cuomo there in 2018. Democratic socialist Julia Salazar was elected to the State Senate, in part, on the strength of her performance in Williamsburg and Greenpoint.

Emily Gallagher (left) in a backyard with supporters after she is endorsed by the New Kings Democrats in October.

Gallagher, running in a district that also includes the Brooklyn Navy Yard and a slice of Clinton Hill, hopes to capitalize on this progressive energy. Her roots in the district run deep. Though she’s not a native, she has been living in Greenpoint since 2006. She is a member of the local community board and co-founded a task force to respond to an uptick in local sexual assaults. In 2016, she ran for the unpaid position of Democratic district leader, losing to the establishment-backed incumbent by 344 votes.

Though Gallagher lost out on a coveted endorsement from the Democratic Socialists of America (DSA made picks in four other Brooklyn races, but not this one), she is backed by a number of progressive political organizations, including the New Kings Democrats, who rose to prominence aggressively organizing reform-oriented voters in the district over the last decade.

“When Emily ran a few years ago, we saw at that time what an impressive leader and voice she is in the community. Since then, there’s even more clarity around her purpose and why she’s running,” said Jessica Thurston, NKD’s VP of Political Affairs. “My hope is that we will be able to send a lot of people to knock doors.”

Thurston argued Lentol, though generally progressive, had failed to address skyrocketing housing costs in the district, as well as environmental challenges. “The incumbent has been in office for 47 years and hasn’t been able to address these problems,” she said. “The fact is there’s clearly an appetite for fresh energy and someone to really engage the grassroots. It’s clear that hasn’t been done.”

Gallagher, who said she was inspired by the wave of progressive insurgents who defeated members of the Independent Democratic Conference in 2018, is running on a leftist platform that should be popular in the district. She supports more state funding for public housing, passing tenant protections to make it much harder for landlords to evict tenants, raising taxes on the wealthy, and reforming the 421-a subsidy to force developers to build more low-income housing. Passionate about environmental issues, she backs increasing funding for the Department of Environment Conservation, which oversees the water quality improvement plan for Greenpoint’s Newtown Creek.

Gallagher is close to the women who formed Albany’s Sexual Harassment Working Group, which successfully fought for new laws to protect staffers who are sexually harassed. Lentol, she said, wasn’t a vocal enough supporter in the years women were suffering. “I wanted somebody to say, it doesn’t matter, this is right, this should happen, we should have a victim-centered form of justice,” Gallagher said.

Another sore point for Gallagher: Lentol was one of the Democrats in the Assembly who voted to block New York City from imposing a fee on plastic bags to cut down on their usage.

But Gallagher’s task of framing Lentol as another out-of-touch moderate won’t be easy.

Like other Democrats in the Assembly, he has been a consistent vote for pro-tenant bills championed by the left. He was a backer of the major pieces of progressive legislation that passed in Albany last year.

As the longtime chair of the Assembly’s Codes Committee, Lentol has been a consistent supporter of criminal justice reforms. He was a lead negotiator in the Assembly last year when Democrats overhauled the state’s bail and discovery laws, a historic moment for progressives in the chamber.

In an interview with Gothamist this week, Lentol was hesitant to give ground to conservatives and moderate Senate Democrats who want to tweak the laws to make it easier for judges to jail defendants with cash bail. “It’s not even three weeks since the bills [became law] and we’re talking about changing them. We have to give it a little bit of time,” Lentol said. “No one is talking about crimes committed by people who make bail.”

In 1995, Lentol did vote to reinstate the death penalty, but told the New York Times in 2004 he was “reassessing” his position. By 2008, the death penalty was effectively abolished in New York State.

Lentol has been the rare Democrat to back legislation to make it easier for the home-sharing colossus Airbnb to operate in New York, a stance that has put him at odds with leftists in Albany and the powerful hotel workers union, the Hotel and Motel Trades Counci [HTC]l. The veteran assemblymember said he went into the issue “blindly,” meeting with hosts who wanted to make more money to help pay their rent.

“Had I realized the dragnet I went into at the time, I may not have done it,” Lentol said at first, before adding: “I still would have done it, it’s the right thing to do. Airbnb and other platforms flourish elsewhere. They ought to be regulated and taxed.”

If Gallagher can enlist HTC, a lavish spender on local campaigns, she may have a chance. But it’s unclear the heavyweight union is joining the fight against a strong incumbent. As of this month, Lentol has banked nearly $350,000 for his re-election. Gallagher only has $23,440 on hand. Local elected officials sympathetic to Gallagher’s cause, like Salazar and Councilmember Antonio Reynoso, have remained on the sidelines.

Lentol also enjoys the unstinting support of Williamsburg’s ultra-Orthodox Jewish community, which typically votes as a bloc and makes it difficult to displace incumbents they favor.

“I keep telling him he can’t retire!” gushed Rabbi David Niederman, a political power broker in the local Satmar Hasidic sect and the president of the United Jewish Organizations of Williamsburg and North Brooklyn. “He is humble and he listens and he works on any issue you bring to his table.”

For anyone who has lived in the district long enough, or has family roots going back a century, the Lentol name is deeply familiar. His grandfather, also named Joseph, served two one-year terms in the same district in 1919 and 1920, winning narrow victories against a Socialist insurgent. (Lentol said his grandfather, despite beating a Socialist, voted against expelling the rest from the chamber during the height of the Red Scare in 1920.)

His father, Edward Lentol, had a longer political career, representing Williamsburg in the Assembly and Senate for 24 years before becoming a State Supreme Court justice. Edward’s ascension to the Supreme Court created a vacancy in the Senate for the local assemblyman to fill. Once the Assembly vacancy opened up in 1972, Edward encouraged his son, a young assistant district attorney in Brooklyn, to run for the seat.

“I’m really proud of having a family history,” Lentol said. “When I didn’t want to run for office, my father talked to me about it and cajoled me to do it. He said it was good to continue the family tradition and I did it.”