New York City has had 109 mayors and they’ve all been men. This year, two women stand a chance of breaking the streak. One-time underdog Kathryn Garcia has surged to the top tier of candidates, and Maya Wiley has seen a relatively united left fall in behind her going into the race’s last two weeks.

What’s taken New York so long, anyway? Of the nation’s 100 biggest cities, about a third have a woman serving as mayor, and others have been led by a woman at some point in history.

We asked a couple of the women who have come close for their thoughts. “Maybe the answer is we’re not quite as liberal a city as we like to imagine,” said Ruth Messinger, who was the first female Democratic nominee for mayor, but lost to incumbent Rudy Giuliani in 1997.

Christine Quinn, the one-time frontrunner in the 2013 election, recalled being coached to tone herself down to be more palatable to voters, a decision she now regrets. “To succeed in New York City — there are songs written about it — you have to be ambitious, you have to be aggressive, you have to be hard-charging, you have to be pugnacious,” she said. “All characteristics that when a woman has them, she’s considered a bitch. When a man has them, he’s considered Chuck Schumer and is incredibly successful.” Experts also cited the historical influence of party machines and unions, and onerous ballot qualification and fundraising requirements among the factors that have held women back.

This time, the decline of those party machines and the advent of ranked-choice voting could help a woman over the finish line — or not. As we’ve stressed before, no one has any idea what’s going to happen in this primary. Women are a majority of the primary electorate, but they’ve never voted as a bloc. “I think this is the first time that there are this many viable woman candidates running,” said Columbia University’s Esther Fuchs. “And women may decide, ‘I’ve had enough of these men. I’m voting to calm things down.’”

IT’S TUESDAY. Got tips, suggestions or thoughts? Let us know … By email: [email protected] and [email protected], or on Twitter: @erinmdurkin and @annagronewold

WHERE’S ANDREW? In Albany with no public events scheduled.

WHERE’S BILL? Holding a media availability.

QUOTE OF THE DAY: “It was a great day for mediocrity.” — a New York litigator re: Cuomo’s Court of Appeals picks.

DAYS TO THE PRIMARY: 14

ABOVE THE FOLD — “Cuomo: Most remaining restrictions to lift once 70% of adult New Yorkers get first vaccine shot,” by Spectrum News’ Shannon Caturano: “Once 70% of adult New Yorkers have received at least one dose of the COVID-19 vaccine, most remaining restrictions will be lifted, Gov. Andrew Cuomo announced Monday. Currently, 68.6% of adults in New York have received the coronavirus vaccine. ‘The light at the end of the tunnel is to remove the remaining COVID restrictions, right? Get to a point where COVID is not inhibiting our society, inhibiting our growth,’ said Cuomo. The governor said capacity restrictions, social distancing rules, cleaning protocols, health screenings and contact tracing requirements will become optional for most places, including retail stores, restaurants, offices and gyms. Unvaccinated people will continue to have to wear masks and maintain social distancing…Some restrictions will still be in place at large venues, schools, public transportation, hospitals and nursing homes, and masks will still be required in certain situations, including mass transit.”

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Yang says he helped win Georgia for Democrats. Some activists beg to differ, by POLITICO’s Tina Nguyen: Andrew Yang has for weeks claimed he was deeply involved in helping Democrats take back the Senate, touting his work in the Georgia runoff as he campaigns for mayor of New York. Last week, during the second televised Democratic primary debate, Yang went a step further, inserting himself into the victories of Sens. Jon Ossoff and Raphael Warnock, both Georgia Democrats, in January’s high-octane runoff election. “I moved to Georgia to help win the Senate,” he told voters, asking if they could “imagine” what would have happened if the Republicans had control of the Senate. “That has given us a lifeline and opportunity to actually get out of this crisis. I’m proud of that work.” But activists on the ground in Georgia paint a more complex picture of Yang’s involvement: that of a man who clearly leveraged his celebrity for the sake of a razor thin Democratic victory — and energetically so — but who may have exaggerated his activity and impact on the race.

Maya Wiley unveils $1 billion plan to create city-sponsored health insurance, by POLITICO’s Amanda Eisenberg: Mayoral candidate Maya Wiley is unveiling a plan Tuesday that would create city-sponsored health insurance for low-income and undocumented New Yorkers — and dismantle a signature 2019 program created by her former boss, Mayor Bill de Blasio, to address the same issue. While the de Blasio administration looked to provide free care to people, it was based largely on services the public hospital system already provided. Wiley’s plan aims to get more than a third of the city’s 600,000 uninsured residents covered with traditional insurance policies.

— FIRST IN PLAYBOOK — Health care union 1199 SEIU is launching a $1.2 million TV ad buy in support of Wiley’s campaign. The new ad, which will air on cable and broadcast TV starting today, features health care workers who fought Covid-19 arguing that Wiley will “fight for frontline workers.” The union, the city’s largest, endorsed Wiley in February. “Maya has always been our number one choice in this race, and we are thrilled to see that her support is growing. Her plans to move our city forward through job creation, investment in community care, and affordable housing will make the difference for families who are working hard to live with dignity in a city that is increasingly pricing them out,” 1199 president George Gresham said.

“As Maya Wiley Pledges to Transform Policing, A Look Back at Her Tenure at NYPD Oversight Board,” by City Limits’ Roshan Abraham: “Four former employees who served under Wiley at the CCRB, who spoke to City Limits on the condition of anonymity, say they were put off by some of her decisions there, including the creation of what they said was an unnecessary position as part of a behind-the-scenes power struggle at the agency.”

— Wiley’s Brooklyn neighborhood is patrolled by a private security force.

— Eric Adams said he would follow the lead of late Mayor David Dinkins on policing.

“Solitary Confinement Reforms Set for City Jails, Even as Advocates Decry ‘Broken Promise,’” by The City’s Reuven Blau: “Two years and a day after Layleen Polanco’s death on Rikers Island galvanized a movement to ban solitary confinement, the de Blasio administration is poised Tuesday to approve new rules it says will effectively end the practice in city jails. But the highly anticipated changes, which would give detainees a minimum of 10-hours outside their cell each day, are strenuously opposed by advocates — including Polanco’s sister — who contend the new regulations don’t go far enough. ‘The mayor made my family a promise that he would end solitary confinement,’ Melania Brown said Monday.”

“NYC’s de Blasio Backs Washington Square Curfew Amid Political Backlash,” Bloomberg’s Peyton Forte

FIRST IN PLAYBOOK — The Retail, Wholesale and Department Store Union is endorsing Corey Johnson for city comptroller. “The RWDSU has proudly worked side-by-side with Corey Johnson for many years,” union president Stuart Appelbaum said of the City Council speaker, citing his opposition to Walmart opening in the city, passage of legislation regulating schedules for retail workers, and support during the fight over Amazon’s scuttled HQ2. “We know that we can rely on him to support unions and workers as NYC’s next Comptroller.”

— Manhattan DA candidate Eliza Orlins is releasing a new plan to assist New Yorkers with disabilities, promising to hire more disabled lawyers, investigators, and researchers in the DA’s office and make physical upgrades to the office to remove hurdles that have dissuaded people with disabilities from reporting crimes and serving on juries. She also says she would take defendants’ disabilities into account in seeking more lenient sentences because of the hardships disabled detainees face at jails and prisons.

ON THE TRAIL — Kathryn Garcia was the only candidate to come out in strong support of Mayor Bill de Blasio’s plan to close Rikers Island and replace it with four new jails at a Tuesday mayoral forum hosted by the 92nd Street Y, City & State and PIX 11. Most mayoral candidates have equivocated on the subject, creating doubt as to whether the multi-year effort to shutter the isolated jail complex was on life support. Shaun Donovan didn’t give full backing to de Blasio’s proposal, but said alternatives should be pursued closer to courts. That sparked pushback from both Maya Wiley and Dianne Morales, who want to close Rikers but not add new jails — and are ambiguous on what alternatives they’d pursue. “The alternative does not have to be a different kind of jail cell — the alternative can be to a life lived in dignity,” Morales argued. Ray McGuire also said he’s “not convinced four vertical jails” is the answer. Scott Stringer and Eric Adams didn’t attend the forum, but have previously voiced opposition to the plan. — Danielle Muoio

“Federal Prosecutors Subpoena Material Related to Andrew Cuomo’s Book,” by Wall Street Journal’s Jimmy Vielkind and Corinne Ramey: “Federal prosecutors have subpoenaed material related to New York Gov. Andrew Cuomo’s recent memoir as part of their probe into Covid-19 deaths in the state’s nursing homes, people familiar with the matter said. Prosecutors working for the U.S. Attorney’s Office for the Eastern District of New York in Brooklyn asked for communications related to Mr. Cuomo’s October 2020 book, ‘American Crisis,’ including contracts and materials used to pitch the book to publishers, the people said.”

“New York Senate Passes Antitrust Bill Targeting Tech Giants,” by Wall Street Journal’s Ryan Tracy

“Final push for parole reforms head to New York Democratic leadership,” by Times Union’s Joshua Solomon: “Democratic leadership in the state Legislature continues to mull how expansive it wants its additional parole and bail reform measures to be in the final week of the legislative session, while advocates continue their attempts to push the reforms they view as very close. … The lawmakers believe they can persuade legislative leaders to push for what they say would be meaningful change to a parole system that a Times Union analysis found has substantial racial divides. ‘The ones who gave us the super majority, they want these things to happen,’ state Sen. Gustavo Rivera, a sponsor of the bill, told the Times Union.”

“Shifting mask policies leads to confusion at schools,” by Spectrum’s Nick Reisman: “Over the last four days, school districts, parents and kids received three different messages for mask wearing by New York state officials. On Friday, it was Health Commissioner Howard Zucker signaling mask rules for both vaccinated and unvaccinated children could ease starting Monday unless the Centers for Disease Control said otherwise. On Sunday afternoon, school officials received an unsigned email from the State Education Department declaring nothing would change. And finally Monday gave the latest iteration of the mask guidance: Kids would be required to wear masks indoors, but districts could have the option of allowing mask wearing to end outside.”

“‘A Great Day for Mediocrity’?: Many Lawyers Left Disappointed by Nominees for NY’s Top Court,” by New York Law Journal’s Ryan Tarinelli: “When Gov. Andrew Cuomo revealed his picks for New York’s top court last month, a parade of glowing statements flowed in the wake of the announcement. But behind the scenes, many attorneys in New York’s legal industry expressed disappointment and surprise at the governor’s decision to nominate Nassau County District Attorney Madeline Singas and Administrative Judge Anthony Cannataro for the state Court of Appeals… Not only are Cannataro and Singas not the best candidates for the court, but their nominations have political overtones, the critics said.”

“Rochester mayor’s husband faces additional drug charges,” by The Associated Press

#UpstateAmerica: Read about the wild ride for Tri-City ValleyCats pitcher Nick White, who went from a reported $350,000 signing bonus from the Miami Marlins to fixing toilets in Oklahoma.

Rep. Bowman calls Manchin ‘the new Mitch McConnell,’ by POLITICO’s Quint Forgey: Rep. Jamaal Bowman on Monday said Sen. Joe Manchin “has become the new Mitch McConnell,” denouncing the West Virginia Democrat for maintaining his support of the legislative filibuster while opposing his party’s expansive election and ethics reform bill. In an interview on CNN, Bowman (D-N.Y.) invoked past comments by McConnell that cast the Republican Senate leader as a partisan obstructionist to the agendas of former President Barack Obama and President Joe Biden. “Now,” Bowman said, “Joe Manchin is doing everything in his power to stop democracy and to stop our work for the people, the work that the people sent us here to do.”

— Cher apologized to Sen. Kirsten Gillibrand for incorrectly lumping her in with Manchin, having confused her with Arizona Sen. Kyrsten Sinema.

“Schumer urges Biden to tap voting rights experts for N.Y. judgeships amid escalating election fight,” by New York Daily News’ Chris Sommerfeldt: “Senate Majority Leader Chuck Schumer urged President Biden on Monday to tap a couple of prominent voting rights attorneys for federal judgeships in New York, signaling Democrats are hoping to bring the national battle over election access into the judicial arena amid partisan gridlock in Congress. Speaking on the Senate floor, Schumer (D-N.Y.) said he first wants Biden to nominate Myrna Perez, the director of New York University Law School’s voting rights and elections program, for an open seat on the prestigious U.S. Court of Appeals for the 2nd Circuit in Manhattan.”

— “Springsteen on Broadway” will be back this month, now the first Broadway show to return.

— The city Law Department got hacked.

— De Blasio pushed for parole reforms and gun control measures in response to the shooting death of a 10-year-old boy.

— Five Democrats are vying for the City Council seat in Queens held by Eric Ulrich, the borough’s only Republican member, while two Republicans hope to keep the seat in GOP hands.

— More than a dozen people were injured when an MTA bus slammed into a brownstone in Brooklyn.

— Actor, activist and former gubernatorial candidate Cynthia Nixon sighting in Albany.

— A judge ruled in favor of AG Tish James’ request for an injunction against the Rensselaer County Board of Elections for failing to provide voters with equitable access to early voting poll sites.

HAPPY BIRTHDAY: Cory Fritz of FTI Consulting … Donald Sussman … Bloomberg’s Patrick Garrigan … Jennifer Dunn of Wells Fargo … Uber’s Matt Wing … Julianna Margulies … CNN’s Sonia Moghe … Jim Cicconi … Avery Brooks … Ben Case … Daniel Elbaum … Jordana Cepelewicz

MEDIAWATCH — The Atlantic’s staff is unionizing with the NewsGuild of New York, and management says they plan to voluntarily recognize the union. … Choire Sicha is joining New York Magazine as editor-at-large. He has been an editor at The New York Times. … Zach Everson is now a staff writer at Forbes covering money and politics. He previously wrote the 1100 Pennsylvania newsletter. Announcement

— Per Talking Biz News: “After more than 2 years working as a columnist at Bloomberg Opinion, Elisa Martinuzzi has now joined the investigations team at Bloomberg as a reporter-editor to cover business, finance and government. … Sally Shin, executive editor of business, tech and media unit, NBC News, is departing. Shin is a veteran NBC News journalist having been with the network for more than 11 years.”

— “Carey Mulligan And Zoe Kazan To Portray The New York Times Reporters Who Broke The Harvey Weinstein Sex Scandal Story In Plan B & Annapurna Drama For Universal,” by Deadline’s Justin Kroll

WHAT DALTON PARENTS ARE READING — “The Private School ‘Awokening’ Panic: What a fun culture war for the world to wake up to!” by Alice Lloyd in the upcoming June issue of P.J. O’Rourke’s American Consequences

FOR YOUR RADAR — “Top White House tech critic Tim Wu holds more than $1M in Bitcoin,” by Daniel Lippman: “His investment in Bitcoin is his largest holding in his financial portfolio. … Wu went on leave from his position as a law professor at Columbia University to join the Biden administration. At Columbia, he made $617,500 over the 16 months before he joined the White House.”

MAKING MOVES: Dennis Poust has been appointed executive director of the New York State Catholic Conference. He had been serving in an interim capacity since January after Richard Barnes resigned from the position last year.

A message from Equinor:

The energy transition is the defining challenge opportunity of our time. Without energy, the world would simply stop. Today, 80% of energy comes from fossil fuels—and the energy system has to change. The world needs energy — but it must be affordable, reliable, and accessible. How will we do it? By accelerating the energy transition. At Equinor, we’re growing our portfolio in renewable energy and cutting greenhouse gas emissions. We’re already planning to power more than 1,000,000 homes in New York with homegrown, renewable energy. But for us, that’s only the beginning. By the time the global population reaches 9 billion in 2050, our goal is to have net-zero emissions. Discover more about Equinor at www.equinor.com/USA.

“Nearly 2/3 of All Manhattan Office Workers Expected Back After Labor Day, Survey Says,” by NBC New York: “The days of remote work for many of Manhattan’s office workers may be numbered, according to a new survey of the island’s largest employers. A whopping 62% of Manhattan’s roughly 1 million office workers could be back in person by the end of September, a Partnership for New York City survey revealed Monday. That number is up from 45% predicted several months ago.”

“Mystery Buyer Pays $157.5 Million for Two Condos on New York’s Billionaires’ Row,” by Wall Street Journal’s Katherine Clarke and E.B. Solomont: “Two condos at New York’s 220 Central Park South have sold for a combined $157.5 million. It is one of the city’s priciest residential transactions of all time. Property records show a buyer paid $82.5 million for a unit on the 60th floor and $75 million for the floor above. The purchase was made through a limited-liability company; the identity of the buyer couldn’t immediately be determined.”