The FlynnStoned Cannabis Company, a dispensary in Syracuse, N.Y., is the size of a large clothing store. Its wooden front doors have iron handles with finials in the shape of cannabis leaves. Inside, nuggets of cannabis flower, infused candies and vaporizers are laid out in glass cases spread over two stories. A lounge under a skylight on the third floor hosts concerts and yoga classes.

It is, by nearly any measure, one of the success stories of New York’s nascent legal marijuana industry. And the man behind FlynnStoned, a 43-year-old high school dropout and roofing entrepreneur named Michael Flynn, appears poised to build a weed empire, with FlynnStoned dispensaries from Brooklyn to Buffalo.

But Mr. Flynn’s hard-charging approach has drawn ire from communities where he is seeking to open more stores. And a recent deal-making spree, in which he has cut branding agreements with dispensaries all over the state to use his name, has drawn the attention of regulators, who are investigating whether he is violating the spirit, and perhaps the letter, of the state’s legalization law.

“They’re trying to stick a pitchfork in me,” Mr. Flynn said.

Mr. Flynn, who has tattoos on his fingers that spell “HIGH VIDA,” is in some ways the type of person whom the state’s legalization efforts were intended to support. His conviction for marijuana possession 25 years ago put him at the front of the line for a state license to sell recreational cannabis products, part of New York’s effort to right the wrongs of the war on drugs.

And in some ways, the success of his business is a bright spot in the state’s troubled marijuana rollout. As others struggled to get off the ground, hamstrung by a combination of complex rules and a slow bureaucracy, FlynnStoned made $30 million in revenue in its first year.

His ambitions have also encountered some familiar roadblocks. Would-be neighbors in New York City have sought to block new stores over concerns about crime and exposing children to marijuana.

At the same time, community boards and state regulators worry that his entrepreneurial attempt to sell the rights to the FlynnStoned name to about 30 dispensaries around the state amounts to preying on marijuana license holders who are less fortunate.

“It seems to not be in the spirit of giving the helping hand to those who were previously adversely impacted by anti-cannabis laws,” said Jesús Pérez, the district manager of a community board on Manhattan’s East Side, where Mr. Flynn is building a dispensary in what was the city’s last Hallmark store. “Just red flag after red flag seems to have come up about this that the community was not comfortable with.”

A Lifelong Calling

Mr. Flynn sees selling marijuana as his destiny.

“I just feel like I’ve been put on Earth to do this,” he said in a recent interview. “I’m just going to keep doing it as long as I’m having fun.”

He said he had started selling weed when he was 12, after his parents divorced and his father disappeared from his life. Left unsupervised, he got hooked on drugs. At 15, he moved out, bouncing among apartments and flop houses before dropping out of school. By the time he was 24, he was carrying hockey bags full of weed across the border from Canada, charging about $2,400 a pound in Syracuse, his hometown, and $4,000 a pound in Florida.

He was convicted of low-level marijuana possession when he was 18, paid a fine and avoided jail. Five years later, he quit drugs and took up roofing.

He started his first business, The Roofing Guys, in 2006. He set himself apart by offering customers financing and, as his main competitors fell to the wayside, he got rich.

“I was so addicted to drugs, alcohol and the party life,” he said. “I turned that around and got addicted to success.”

It has afforded him a different life with his wife, Angela, a high school classmate who gave him a Home Depot credit card in her name to help start the business. The couple have five children and live on a custom-built estate in the middle of a cornfield near Syracuse.

When New York legalized recreational cannabis in 2021, Mr. Flynn’s demonstrated ability to run a business and his marijuana conviction helped him win a license to open one of the state’s first legal dispensaries.

On Instagram, he shared video from the ribbon-cutting ceremony in June 2023 interspersed with photos of his lime-green Lamborghini Aventador and a diamond necklace bearing his store’s name encircling a green marijuana leaf. The video was set to a song called “Blow Up” by the rapper J. Cole, who sings, “This is a song for my haters/ Y’all got me feeling like the greatest.”

As FlynnStoned grew, so did the opportunities its founder began to see fanning out before him.

Building the Brand

Under New York’s legalization law, one shop owner is not allowed to control more than three dispensaries.

Mr. Flynn, regulators say, may have found a way to skirt that law.

In the wake of FlynnStoned’s success, other dispensary owners began reaching out to Mr. Flynn for help and advice, he said. Soon, he started to make deals with some of them.

Those deals allowed other dispensaries to use the FlynnStoned name in exchange for a small cut of their revenue, he said. Mr. Flynn added that he also connects the business owners with friends who are investors but “not Wall Street guys.”

“At first it was advice and help, and then it became, well, why don’t we just build the brand and help ourselves, too?” he said.

Mr. Flynn said the branding agreements do not make him an owner or investor. He declined to say how much revenue he takes, except that it was “not that much.”

But state officials have begun scrutinizing the deals, seeking to prevent big players from taking advantage of small, local business owners whom legalization was supposed to benefit. James Rogers, the director of a new unit within the Office of Cannabis Management that investigates potential ownership violations, said licensees were free to sign agreements that make their businesses work. But he said his team would unwind deals that give investors too much control.

“It’s the predatory behavior that we’re after,” he said.

The agency declined to say whether it was investigating Mr. Flynn, though Mr. Pérez, the community board official, said that was what he had been told by state officials. Mr. Flynn also said the agency was blocking some of the deals.

Robert Grannis, a 54-year-old farmer, got a license in 2022 and plans to open a FlynnStoned store in Binghamton. He said he had sought Mr. Flynn’s help after the state failed to provide the financing and real estate that it had promised to help early licensees open dispensaries.

Mr. Flynn initially offered to buy his license, Mr. Grannis said, but they settled on a branding deal, and Mr. Grannis took on an investor who paid for renovations. He declined to discuss the terms.

Mr. Grannis said the deal gave him peace of mind because he had heard horror stories of people building out their stores only for regulators to deny or delay their openings. Unlike liquor stores, cannabis licensees receive their final licenses only after their stores are built.

He said that what Mr. Flynn was doing in the cannabis industry was no different than what Starbucks did for coffee or McDonald’s did for hamburgers.

“We’re not doing anything but the American dream,” he said.

Axel Bernabe, a lawyer who helped to write the state’s legalization law and the rules for the market, helps Mr. Flynn structure the deals. Some industry insiders have criticized his involvement, but Mr. Bernabe said there is nothing wrong with what he or Mr. Flynn is doing.

“This idea that this is super shady is mudslinging business,” Mr. Bernabe said, adding, “It’s a play on building your brand, and everybody’s trying to do that.”

An Unexpected Turn

The deals had proceeded smoothly until Mr. Flynn began expanding in New York City, drawing vociferous backlash.

Residents protested his plan to put a dispensary in the former Hallmark store, near the United Nations. In Greenwich Village, where he is converting what had been an adult video store into a FlynnStoned, the community board dug up videos of him and others smoking at his Syracuse store, which is not allowed. A petition to stop him from opening another location in the Greenpoint Savings Bank building in Brooklyn also gained hundreds of signatures.

“I’m not anti-pot, but I am anti-dispensary,” said Tanya Arias, a Realtor who has lived around the corner from the Hallmark store site for 20 years. “It’s not a store that’s going to service the needs of our community.”

Mr. Flynn’s own words may cause him the most trouble. In September, he told the East Side community board that he was the sole owner of the forthcoming dispensary, that he had already signed a lease and that the Hallmark store’s owners had not paid their rent in months.

None of it was true.

He said he had not expected the opposition, but he bristled at questions that he felt were intrusive. “Whatever I said in that community board was just whatever I had to say to get the hell out of there,” he said.

Kuljot Bhasin, 63, who owned the Hallmark store with his wife, Amrita, sued Mr. Flynn for defamation. They are seeking at least $4 million in damages. Mr. Flynn’s defense lawyers said their client had not spoken maliciously.

“To come and disparage us to make himself look good to the board, that infuriated us,” Mr. Bhasin said in an interview.

Mr. Bhasin, a Sikh American immigrant, said he plans to reopen the business in a new location. But a part of him hopes that Mr. Flynn’s plans fall through, he said, so that he might be able to return to the shop where he sold cards and gifts for 22 years.

Alain Delaquérière contributed research.

A Newark federal judge on Friday heard arguments on whether the case to free Mahmoud Khalil, a leader of pro-Palestinian protests at Columbia University, should continue to play out in New Jersey or be transferred to Louisiana, a potentially more favorable venue for the government’s case.

The judge, Michael Farbiarz, did not make an immediate decision, but is expected to rule soon. Mr. Khalil, a legal permanent resident, was detained on March 8 at his New York City apartment, sent briefly to a New Jersey detention center and now has been held for nearly three weeks in a facility in Jena, La.

While Mr. Khalil’s lawyers are fighting for his freedom, the Trump administration is seeking to deport him, saying that he spread antisemitism through his involvement in the protests. If Mr. Khalil stays in Louisiana, his case could end up in one of America’s most conservative appeals courts. Those judges could decide whether the government’s rationale for detaining Mr. Khalil could be used in other cases.

The case was originally filed in New York, but a judge there decided he lacked jurisdiction and that it should be heard in New Jersey. The attempts by Mr. Khalil’s lawyers to free him have created a tangle of litigation, much of which has focused on a seemingly technical question: In which court should his case be heard?

On Friday in Newark, Baher Azmy, a lawyer for Mr. Khalil and legal director of the Center for Constitutional Rights, argued in court that transferring the case to Louisiana would set a precedent for other activists to be moved without legal justification, which he called “Kafkaesque.”

The government’s case against Mr. Khalil was undertaken “in order to retaliate against constitutionally protected speech,” Mr. Azmy said.

But a lawyer for the government, August E. Flentje, said it “made no good sense” for the case to be heard in New Jersey when Mr. Khalil had been arrested in New York, asserting that “the case belongs in Louisiana.”

Judge Farbiarz delayed ruling on a request from Mr. Khalil’s lawyers that he be granted bail, saying he first wanted to resolve the issue of where the case would be heard.

Mr. Khalil is one of at least nine protest participants who have been arrested and detained this month. Unlike some others, he is a legal resident, married to an American citizen who is expected to give birth next month.

He has not been charged with a crime. Instead, the secretary of state, Marco Rubio, has cited a rarely used law to explain Mr. Khalil’s detention, saying that the recent graduate threatens the Trump administration’s foreign policy goal of halting the spread of antisemitism.

Mr. Khalil’s lawyers initially asked for his release in New York federal court. But the judge there determined that it should be heard neither there, nor in Louisiana, but in New Jersey, where Mr. Khalil was being held at the moment his lawyers filed court papers. Accordingly, the case itself was transferred to New Jersey last week.

Once there, the government’s lawyers continued to fight to transfer the case to Louisiana. In a filing, they noted that Mr. Khalil had never filed a petition in New Jersey — and argued that the court had no jurisdiction.

The administration has reason to continue its fight. If the legal battle is waged in Louisiana, it is likely to make its way to the U.S. Court of Appeals for the Fifth Circuit, which from New Orleans presides over cases from that state.

The Fifth Circuit is known as one of the country’s most conservative, and in the past has sided with government officials over noncitizens. If its judges rule in favor of the Trump administration, Secretary Rubio could continue to cite the law used to justify the detention of Mr. Khalil in efforts to deport other legal permanent residents.

Friday’s hearing came days after a judge in Manhattan ordered the government to halt efforts to detain Yunseo Chung, a 21-year-old Columbia student and legal permanent resident who had participated in pro-Palestinian protests. Ms. Chung, who shares a legal team with Mr. Khalil, was never detained by immigration authorities.

In an interview outside the courthouse after the hearing, Mr. Azmy noted the distinction between her case and Mr. Khalil’s.

“The fact that he’s in custody allows the government to have total control over him,” Mr. Azmy said.

As the hearing played out, around 50 demonstrators assembled outside the Newark courthouse to protest Mr. Khalil’s detention. They waved Palestinian flags, held signs and chanted.

“Hands off our students! ICE off our campus!” read one sign. “Opposing genocide does not mean supporting terrorism.”

Speaking at the rally, Amy Torres, executive director for the New Jersey Alliance for Immigrant Justice, pointed to a chilling effect on free speech created by the detention of students across the country.

“They have only targeted people that they view to be voiceless,” she said, adding, “This is about this administration taking the issue that they believe is the least sympathetic, and making an example out of the people that they arrest.”

Jonah E. Bromwich contributed reporting.

Being the front-runner in a race for mayor of New York City often comes with exceptional scrutiny. But few have presented their opponents with quite as many targets as former Gov. Andrew M. Cuomo.

In the weeks since Mr. Cuomo joined a crowded Democratic primary field and immediately catapulted to its front, a group of New Yorkers whose relatives were nursing home residents who died of Covid have repeatedly blamed him for their suffering.

Women’s groups have picketed his campaign events to remind voters of the sexual harassment accusations that drove him from the governor’s office.

Then, on Thursday, years-old sworn testimony surfaced in The New York Post describing Mr. Cuomo and his longtime top aide, Melissa DeRosa, as having been in an “emotionally intimate” relationship.

Mr. Cuomo’s proximity to Ms. DeRosa would seem to have little bearing on his qualifications to be mayor. But the sudden re-emergence of the long-denied rumors underscored how his tenure as governor left Mr. Cuomo with a lengthy list of enemies and political baggage ripe for attack.

For now, Mr. Cuomo has maintained a comfortable polling lead against nine Democratic challengers, including Mayor Eric Adams. Yet as New York City political history has long demonstrated, a perceived lead comes with real risks — especially months before Primary Day.

“When you’re the only game in town, you’re the only person to take down,” said Mike Morey, the campaign spokesman for then-Council Speaker Christine Quinn in 2013, who watched her early polling lead in that year’s mayor’s race collapse. “You’d probably rather be second or third place and just climbing.”

New York City lets voters rank up to five candidates in order of preference on their primary ballots. Opponents of Mr. Cuomo and Mr. Adams are trying to stop their ascent by popularizing the acronym D.R.E.A.M., or “Don’t Rank Eric or Andrew for Mayor.”

Mr. Cuomo’s result may well be different than Ms. Quinn’s. He is better known and more battle-tested than almost any of his predecessors. His allies believe that that he can prevail as long as he can redirect voters’ attention toward his record of accomplishment during roughly a decade as governor, during which New York State legalized same-sex marriage, raised the minimum wage and rebuilt LaGuardia Airport.

“New Yorkers know the city is in crisis and Governor Cuomo is the only candidate in this race with the experience and the record of results to help fix it and make it a safer and more affordable place for all,” said Rich Azzopardi, Mr. Cuomo’s spokesman. “This is why these petty attacks are falling on deaf ears.”

But as Mr. Cuomo’s opponents are eager to point out, his tenure in Albany was also marked by turmoil, controversy and heavy-handed tactics that have left him with higher unfavorable ratings in recent polls than any candidate except Mr. Adams.

“The fly in the ointment is that he’s not particularly lovable,” said Mark Green, who narrowly won the 2001 Democratic primary for mayor, only to lose in the general election to Michael R. Bloomberg.

Those trying to stop Mr. Cuomo have been far more vivid. On Sunday, nine mayoral candidates gathered in Brooklyn alongside relatives of nursing home residents who died of Covid-related complications during Mr. Cuomo’s governorship. They hammered him for his policy directing nursing homes to admit hospital patients who had tested positive for the coronavirus.

“Could any other issue bring us all together with the differences that we have?” said Curtis Sliwa, the Republican candidate for mayor. “No — it’s the death, the unneeded death, of all these folks who were trusting the governor to do the right thing.”

Mr. Cuomo has said the state’s public health policies, including those involving nursing homes, adhered to federal guidelines, and he has accused federal authorities of trying to scapegoat him politically.

That controversy was largely eclipsed by accusations, including from former state employees, that Mr. Cuomo had sexually harassed them. The claims prompted an investigation by the office of the New York attorney general, who concluded in August 2021 that Mr. Cuomo had harassed 11 women.

He resigned within days of the report’s release, though in the years since, he has spent millions of dollars in legal fees fighting to clear his name. He denies any wrongdoing.

It was in March of that year, around the time that Mr. Cuomo was facing the first of those accusations, that The Daily Mail approached the governor’s office with questions about his relationship with Ms. DeRosa. It was preparing to publish photographs that showed the pair seated close together, huddled in conversation over drinks at a Manhattan restaurant.

Ms. DeRosa was also concerned that the outlet would publish longstanding rumors that she and Mr. Cuomo were more than just colleagues. She called Josh Vlasto, who had previously served as Mr. Cuomo’s chief of staff and who was an informal adviser, for advice on dealing with the publication, according to Mr. Vlasto’s testimony during the sexual harassment investigation.

In the transcript of that testimony, Mr. Vlasto is quoted as saying that Ms. DeRosa, who was married at the time, told him she did have an “emotional romantic relationship with the governor,” but said that the two had never been sexually involved.

“Emotionally intimate was the words she used,” Mr. Vlasto said. “I didn’t press on what that meant.”

The former governor’s younger brother, Chris Cuomo, was also brought in to brainstorm a response, according to Mr. Vlasto’s account. “He had said do you intend to be together in the long-term or do you intend to be together after you’re in office,” Mr. Vlasto said of Chris Cuomo. “She said I don’t know.”

The trio agreed that Ms. DeRosa would deny a romantic relationship to The Daily Mail; Ms. DeRosa ultimately told the publication that she and the governor “never had an intimate relationship.”

Mr. Vlasto testified that after The Daily Mail published the photographs, Ms. DeRosa told him that she had not had a romantic relationship with Mr. Cuomo, contradicting her earlier account.

Months later, in her own testimony in the sexual harassment investigation, Ms. DeRosa also denied having had a romantic relationship with Mr. Cuomo.

Investigators separately asked Mr. Cuomo whether he had had any romantic relationships with members of his staff.

“Never,” he said.

On Thursday, after The Post published its article, both Catherine M. Foti, a lawyer for Ms. DeRosa, and Mr. Azzopardi reiterated that there had been no physical relationship between Mr. Cuomo and Ms. DeRosa.

“Of course after seven years of working together for New York, the governor and Melissa were emotionally close,” Mr. Azzopardi said. “We all were after going through Covid and everything else together.”

Mr. Vlasto declined to comment.

The interview with Mr. Vlasto took place in the summer of 2021, but Mr. Vlasto’s account of Ms. DeRosa’s request was not reported before Thursday.

The transcript of his testimony posted on the attorney general’s website is redacted, and it conceals Ms. DeRosa’s name and much of Mr. Vlasto’s remarks about her and Mr. Cuomo. But an unredacted version of the transcript was posted briefly in 2022 as part of a broader tranche of investigative materials, before it was taken down and replaced.

A spokeswoman for the attorney general, Letitia James, said the unredacted version had been posted by accident, and that it had only been up for two hours.

The New York Times was able to access the unredacted transcript of Mr. Vlasto’s testimony using The Internet Archive’s Wayback Machine, which preserves web pages.

Mr. Azzopardi, though, called for an investigation into how the unredacted transcript became public. In a statement, he accused Ms. James of using “lawfare” to harm Mr. Cuomo and of helping to resurface the transcript as part of a “transparent ploy” to aid one of his rivals in the mayor’s race, Adrienne Adams, the City Council speaker.

The spokeswoman for Ms. James declined to comment on the accusation.