After several months of searching for a new leader for the nation’s largest school system, Barbara Jenkins, the superintendent of Orange County Public Schools in Florida, emerged this week as a contender for the job.

City Hall is still courting the Orlando schools chief, according to a source. But there are several big reasons why Jenkins might not be New York City’s next school’s chancellor — as well as some unusual behind-the-scenes discussion that could help draft Jenkins or other out-of-state superintendents.

One is that Jenkins has voiced concerns about taking the job, according to multiple sources with knowledge of the search. Some said she signaled weeks ago that she was not interested.

Another is that she may not have the union support that has proven valuable to Mayor Bill de Blasio. She definitely doesn’t have the support of Randi Weingarten, the influential leader of the American Federation of Teachers.

Weingarten told Chalkbeat this week that she was “surprised” to hear Jenkins’ name surface, and compared her to leaders of the so-called education reform movement who have had contentious relationships with teacher unions.

I think that Barbara Jenkins is much more in line with the Joel Klein and Michelle Rhee types than she is in line with the Carmen Fariña types,” Weingarten said, comparing the polarizing former schools chiefs of New York City and Washington, D.C. to the city’s current schools chancellor.

Fariña, who has held the top job since 2014 and announced she was stepping down in December, was brought in partly to undo Klein’s policies and has taken a friendly stance toward the city’s United Federation of Teachers. (UFT President Michael Mulgrew declined to talk about discussions he has had with City Hall about Fariña’s successor.)

A third potential issue: compensation. Jenkins made $310,000 in 2017, according to the Orlando Sentinel, while Fariña’s salary is roughly $235,000. A move could mean Jenkins, who is in her late 50s, would have to forfeit some of her future pension, after spending years in the same district, and contend with the high cost of living in New York City.

Those factors could be a problem for many potential candidates, says Kathryn Wylde, the president and CEO of the nonprofit Partnership for New York City, which serves as the business community’s lobbying group. That’s given rise to conversations about whether the chancellor’s compensation could be supplemented — perhaps by a third party, such as an individual who is interested in education. (The Partnership for New York City is not working to find additional funds, she said.)

“It’s understandable that it would be difficult to attract somebody to the city because of our high costs,” Wylde said. “Perhaps that’s something we ought to be trying to address.”

Still, Jenkins generally fits within the profile de Blasio has sketched out for the next schools chief. She has years of experience running a school system with over 200,000 students, and the district has earned praise under her leadership. If chosen, she would be the first black woman to lead New York City’s school system.

Jenkins and Mayor Bill de Blasio declined to comment.

Patrick Wall contributed reporting.