For years, the principal of Springfield’s Chestnut Middle School Talented and Gifted had two identities: living at home as a man, but known as a woman to the school community.

This week, Declan O’Connor will finally be true to himself, telling parents and students at Chestnut TAG that he is a transgender man.

He is the third school principal in Massachusetts to publicly come out as transgender.

“Last summer, I realized that I was really living two different lives,” O’Connor said last week in an interview in his school office — where a plate carrying his former name, Colleen O’Connor, still hung outside. “I had my internal and personal identity that didn’t align with my public persona and identity. And I just got tired of carrying the burden of having two identities — one that was true and one that was a safer way to move through the world without coming out.”

O’Connor recently told school staff about his gender identity. He sent a letter to families, timed to arrive in Tuesday’s mail. The school will inform students Wednesday.

“After much soul searching, I realized that I have an obligation to my communities, and myself, to be my fully authentic self in every area of my life,” O’Connor wrote in the letter.

It is the first public step O’Connor is taking on a journey he always kept private.

Chris Gabrieli, chairman of the board of the Springfield Empowerment Zone, a group of schools that includes Chestnut TAG, called O’Connor an “outstanding principal” who has the board’s support.

“We believe that the principals who lead the school should be principals who do a great job for students and who build a strong community with teachers,” Gabrieli said. “Dr. O’Connor’s gender identity ... doesn’t change any of that.”

Gabrieli said of O’Connor’s decision, “I honestly consider it consistent with his leadership as a principal that it would be done with style and grace and courageousness and transparency. That’s exact how he’s led the school.”

O’Connor, 49, grew up in a working-class town in Connecticut. He moved to Western Massachusetts to attend Elms College and fell in love with the region.

In 1996, he took a job teaching English at Springfield’s Central High School. He later worked as a literary coach and director of English language arts for the Springfield school district. In 2014, he was hired as a turnaround principal to lead Chestnut Talented and Gifted, one of three schools created out of the struggling Chestnut Middle School. He earned a doctoral degree in educational leadership at the University of Pennsylvania while working as principal.

At Chestnut TAG, O’Connor focused on improving the teaching staff. Around one-third of teachers left after his first year, he said.

Health and physical education teacher Molly Smith said O’Connor earned a reputation for having high standards and being “firm but fair.” Between 2015 and 2018, rankings based on the state’s accountability standards saw Chestnut TAG rise from the ninth percentile among all Massachusetts schools to the 55th percentile.

The Springfield Empowerment Zone recently chose O’Connor and two other principals for its “Building With Our Best” program, which expands the roles of top-performing educators. Next year, O’Connor will become executive principal of Chestnut Impact Preparatory, in addition to continuing his duties at Chestnut TAG.

O’Connor had kept his gender identity private throughout his career, although he has identified as male in his personal life for a decade. He worried coming out publicly would hurt him professionally, and he was reluctant to divulge such personal information.

Wearing a suit, with his hair cut short, O’Connor said he has always looked masculine. He wonders if people speculated about his gender identity, but he resisted putting a name to it.

“One thing I find fascinating and frustrating is I can look this way and be this way, but when you name it, it becomes something very different for people,” he said.

When O’Connor was 4 years old, he knew he didn’t want to wear “girl clothing.” He did not focus on gender identity as a teenager. In his 20s, he began to acknowledge it, recognizing that the person he was in his mind did not align with the person he saw in the mirror.

“I had somebody close to me ask me if I was transgender, and I’d never heard that word before,” O’Connor said.

Declan O'Connor stands for a portrait in the school's hallway. (Don Treeger / The Republican)

Neither did he have a single moment where he “transitioned.”

“I just made one decision at a time to make changes for myself that helped me feel more comfortable and more male,” he said.

O’Connor has been married to his wife, Michelle O’Connor-St. Pierre, for a decade. He said his family and friends have been supportive.

Last year, frustrated and exhausted with living a dual identity, O’Connor gave himself a deadline of the end of this school year to decide whether to come out in his professional life. “I was getting too old to keep batting this decision around, and I wanted to make peace with myself around it,” he said.

O’Connor recalled a conversation with a therapist who had a suicidal transgender boy as a patient. The boy said he needed to see more transgender people in the world.

“I’m certainly not doing this for anyone else. I needed to do this for myself and for my family,” O’Connor said. “But I also recognize that there are a lot of transgender people that need hope and need to see more people represented in positive ways.”

O’Connor recently changed his name to Declan, choosing a name he liked. He legally changed his gender, from female to male.

Legally, transgender people in Massachusetts are protected from employment discrimination. A high-profile 2016 law extended anti-discrimination protection to all public places, and voters defeated a 2018 ballot question that would have repealed the law.

Smith said she hopes O’Connor’s public affirmation helps students who are struggling with their gender identity or sexual orientation. Studies have shown that people who are transgender — as well as gay and lesbian — have high rates of attempted suicide. Students are frequently harassed.

“In a way, it’s exciting because it will show our students, not only our transgender students but all of our students, that people are different and it’s okay ... and you might identify as something that’s not binary or ‘traditional’ and that doesn’t mean that you can’t live a full and happy life,” Smith said.

Other school administrators who have made similar transitions have had mixed experiences.

Asa Sevelius, the principal of Heath School in Brookline, was the first principal in Massachusetts to come out publicly as transgender. Sevelius has said he felt supported and welcomed by his school community since making his announcement via email in June 2017.

“The avalanche of warm wishes was ceaseless, for days and days as my story reached larger and larger circles of folks,” Sevelius wrote in a post on the website of GLSEN, a national advocacy organization for LGBTQ students. “I was overwhelmed. I was ecstatic. I was relieved.”

But in Swampscott, parents held a no confidence vote and Principal Shannon Daniels’ contract was not renewed after Daniels publicly identified as gender fluid, according to news reports.

Genny Beemyn, director of the Stonewall Center at the University of Massachusetts Amherst, a resource center for the LGBTQ community, said one challenge people often face coming out as transgender is that some conflate gender identity with sexual orientation, and have misperceptions about what transgender means — particularly in a school setting.

“People who are not educated really jump to ‘this is sexualizing our children,’ when this has nothing to do with sex or sexuality,” Beemyn said. “It’s someone being able to be their authentic gendered self in a workplace setting, which everyone should have a right to do.”

Ev Evnen, interim director of the Massachusetts Transgender Political Coalition, said the biggest challenge many transgender people face coming out is encountering transphobia.

“Trans folks face the perception that we are deceiving people or are in some way, shape or form different in a way that is dangerous and that is a threat,” Evnen said. “This is rooted in a fear of the unknown rather than in any sort of reality.”

Evnen said that can be heightened when a transgender person holds a visible community role. At the same time, Evnan said for a principal to come out as transgender, “It’s really a message of commitment to the lifelong process of knowing yourself and living out your truth. ... It’s a really great example to set for young people of being authentic to who you are.”

O’Connor said he understands some people will have biases, but he hopes knowing someone who is transgender will help address bias.

“I generally believe in the goodness of human beings, and I think that all I can do is be honest and real and see what happens,” he said.