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Bill de Blasio's persistent courting of New York City's Orthodox community has reached a crossroads, two years into his mayoral administration.

The mayor has lavished favors on the Orthodox, restoring key political goodies that his predecessor, Michael Bloomberg, eliminated, and creating major new programs with the Orthodox in mind.

Yet for all those gestures, it's now far from clear that the mayor will be able to count on the powerful Orthodox vote during his reelection run, just over a year away. Revelations about federal corruption investigations involving Orthodox donors and the mayor's fundraising apparatus have cast a pall over the Orthodox community, with names and photos of Orthodox Jews showing up daily in city tabloids in connection with the probes.

"He's tried harder on the cultural issues than Bloomberg ever did," said Michael Tobman, a Brooklyn-based political consultant who works frequently in the Hasidic community. "It's a little messier, that's all. There are Orthodox bundlers wrapped up in a scandal. Who likes that?"

The city's Orthodox population is large and growing, and tends to vote in a well-organized set of blocs, making it a plum prize for citywide elected officials.

Bloomberg, who paid for his own political campaigns and took no donations, dealt harshly with the Orthodox on religious and cultural issues. De Blasio, who lacks Bloomberg's personal wealth, has been forced to play an old-fashioned machine politics game, seeking a more transactional arrangement with Orthodox leaders.

So far in his first term, de Blasio has removed many of the irritants that Bloomberg imposed on the community. In 2015, he lifted Bloomberg's controversial restrictions on the metzitzah b'peh circumcision rite. He restored funding in 2015 for some of the childcare vouchers that Bloomberg had eliminated. He rolled back Bloomberg's special education reforms.

De Blasio also instituted a universal pre-kindergarten program that gives city funds to not-for-profits to run private school programs for four year olds, which he has said he created with Orthodox in mind. And he approved, following negotiations with the City Council, a controversial and expensive program to provide private security guards to religious schools.

He's even made efforts to ease congestion on Boro Park's streets.

"The difference is really access," Goldenberg said. "Hearing, understanding, and thinking about it."

Now, the ties that de Blasio has carefully cultivated could be under threat. De Blasio's progressive agenda on social issues has always been in contrast to the beliefs and positions of many in the Orthodox community. And while the leadership has been willing to overlook those differences, that could change if the relationship continues to sour.

Two Orthodox donors to de Blasio's 2013 campaign and his nonprofit the Campaign for One New York, Upper West Side real estate developer Jona Rechnitz and Boro Park police aficionado Jeremy Reichberg, are reportedly at the center of a federal corruption probe, one of a number of investigations currently rocking City Hall and the New York City Police Department.

Neither Rechnitz nor Reichberg were major figures in Orthodox communal politics, but the investigations are drawing new attention to the steady flow of friendly political gestures that have streamed from City Hall to Orthodox enclaves like Boro Park and Williamsburg.

Relations appear to be strained between Orthodox leaders and the de Blasio administration. The executive vice president of the powerful Orthodox umbrella group, Rabbi Dovid Zwiebel, declined to speak for this story, although de Blasio has appeared at his organization's gala dinner. Maury Litwack, director of state political affairs at the Orthodox Union Advocacy Center, did not respond to requests for comment.

When de Blasio ran for mayor in 2013, he found an Orthodox community that was frustrated after a dozen years under Bloomberg. As conservative-leaning New Yorkers, many approved of the mayor's success rebuilding the city's economy after September 11 and keeping crime rates low. But as Orthodox Jews, they harbored a distinct sense that Bloomberg, despite being Jewish himself, simply didn't like them.

Bloomberg spent his tenure chopping away at key political goodies that the Orthodox had won over years of coordinated voting and disciplined political work. The mayor cut funding for childcare vouchers disproportionately used by Orthodox Jews, and he made it harder for parents to get the city to pay for private schools for special education students, a major issue for Orthodox families. Bloomberg also imposed restrictions on a potentially dangerous circumcision rite long overlooked by city health authorities.

"No one ever felt that there was this kinship and familiarity with us" from Bloomberg, said Ezra Friedlander, founder and CEO of the Friedlander Group, a political consultancy specializing in ultra-Orthodox clients.

Despite his progressive politics, de Blasio seemed an obvious pick to many Orthodox activists, particularly in Boro Park. A former City Council member representing the neighborhood, he had close friends in the leadership of its large Bobov Hasidic sect , and on the Agudath Israel board.

Even the Boro Park street corner trash bins, bought with de Blasio's appropriations during his time in the Council, bore his name.

"He's been to my house on a Friday night," said Leon Goldenberg, an Agudath Israel board member and longtime de Blasio supporter. "It creates a different kind of relationship."

De Blasio raised $10 million from residents of the two main Boro Park zip codes for his mayoral campaign. Joe Lhota, his Republican competitor, raised just $3.5 million.

Other Orthodox communities were slower to back de Blasio. Hasidic sects in Williamsburg supported Bill Thompson during the Democratic primaries, and Syrian Jews in Flatbush favored Christine Quinn. On the day of the general election, de Blasio won the parts of Boro Park that he had represented in the City Council, though he lost the neighborhood as a whole to Lhota by a narrow margin.

The lesson de Blasio took from the 2013 results in Boro Park, according to one Jewish communal official active in city politics, was that the Orthodox community was a winnable constituency despite their conservative politics if he continued to show that he could serve their particular needs.

"Because the Boro Park voters who lived in the district he represented as a council member voted for him, one conclusion that he and his campaign draws is that the more he is known as being willing to serve the communities, the more likely they are to vote for him," said the official, who asked not to be named to protect relationships.

That's led to a persistent campaign of friendly treatment towards the Orthodox.

Now, amid the swirl of investigations into de Blasio's political fundraising, observers are taking a second look at that positive treatment.

Rechnitz and Reichberg both donated to de Blasio's campaign, and served on the mayor's inauguration committee. They are reportedly under investigation for their relationships with high ranking police officers, some of whom have already been disciplined by the department. The Forward reported on April 6 that Reichberg flaunted his connections to the mayor to exert influence at the police precinct in Boro Park.

Questions also remain about the mayor's role in a scandal surrounding a Lower East Side nursing home, in which an obscure move by a city agency allowed a Hasidic businessman who is a member of the Bobov community to clear millions by selling the home to a condo developer.

What remains unclear is whether, when the funk of the scandals clear, all of that positive treatment will have been enough to win de Blasio lasting goodwill among the Orthodox rank-and-file.

Friedlander, the political consultant, said that he believes that de Blasio is popular in Boro Park. "I haven't heard one complaint about Bill be Blasio," he said.

Still, others acknowledge a cultural divide. Michael Fragin, an Orthodox political analyst, said that, from an Orthodox perspective, de Blasio and his team can seem distant from Orthodox concerns. "Many of them are very wedded to certain progressive orthodoxies," Fragin said. "And those don't always include groups that are not in sync with them, such as the Orthodox."

Meanwhile, leaders struggle to manage the expectations of the community that's eager to take advantage of de Blasio's friendship. "There are [Orthodox people] that would like [that] everything that we ask for, we should get," said Goldenberg, the Agudath Israel board member. "But the reality is we're living in a progressive city… In New York City, we're an anomaly."