Cheryl Katon’s improbable choice

But at home and with her family, the person known as Chuck at work was Cheryl Katon, a trans woman with a radiant smile and a love of brightly colored blouses and bold necklaces. She had been married to her wife, Jenn, for more than 20 years and they’d raised two children. The family was active in their Unitarian Universalist church. Many nights, after work, Katon would transform into Cheryl and head out to give speeches and organize fund-raisers in her role as a leader in Boston’s trans community.

A week after the new Boy Scouts policy was announced, Katon was interviewed on NECN as Chuck, wearing a dark suit and blue tie. Don’t be too giddy, she thought to herself, but the grin on her face was undeniable. The news was wonderful for both the trans Scouts she knew, and for the organization that had meant so much to her growing up.

Katon, 54, had been a Scout since second grade. She credits the experience with helping shape the confident, resilient adult she would become. And yet changes she would make as an executive — some intended to make Scouting more inclusive, some just adjustments to old ways of doing things — would generate fierce opposition among a small number of traditionalists.

But these problems had yet to unfold. The announcement came before more people in the local Scouting community found out their CEO was a trans woman, before the false accusations at work, and before the threats started arriving. But even as Cheryl Katon hoped the new policy would make a difference, she had long known she might one day need to make an impossible decision: between the organization she loved and the person she needed to be.

Cheryl Katon grew up in Quincy, the middle child of a nurse from New Bedford and a father from Dorchester who worked his whole career for the phone company. Katon’s parents separated when she was 7. Her father got a place nearby, but Katon didn’t see him much.

Katon was about 11 when she started exploring her gender identity, collecting old clothes from her two sisters and hiding them at the bottom of her closet. When she pictured herself walking to school as a girl, she was always laughing with a group of friends — a happier version of the boy who in fact walked alone. Under her bed was an envelope of articles she’d clipped about drag queens and men who identified as female. One day, the articles were gone — taken by her mother, she suspected, without a word.

Around the same time, Katon took over a 5 a.m. newspaper delivery route from a neighborhood girl. One customer, unaware of the change, continued to leave payment envelopes addressed in neat, looping handwriting to “paper girl.” When Katon finally met the customer, and found the envelope made out to “paper boy” the next week, she felt a twinge of sadness.

But in the Scouts, Katon felt part of something bigger, like she belonged. Katon loved everything about it: earning badges for horsemanship, rope tying, and canoeing, and the positive feedback that came with each success. She loved climbing trees and camping with the boys from the West Quincy neighborhood where she went to Catholic school and where her troop met every Wednesday night in the basement of St. Mary church. They’d carpool to meetings, and a Scout leader later taught Katon to drive. On awards nights, when fathers pinned new badges to their sons’ shirts, Scoutmaster George Kanelos did the honors for Katon.

Katon’s mother had hoped Katon would find male role models in the Scouts, and the scoutmaster, known as Mr. K to the kids, became a father figure. A Vietnam veteran, Mr. K instilled values in Troop 32 that he learned in the Army: work together, look out for one another, help your buddy. Katon always had a great Scout spirit, Kanelos recalls today, embodying the values of kindness and trustworthiness. Eventually, Katon and about a dozen fellow troop members made it to Eagle Scout, the highest rank possible. For more than a decade, Katon has organized an annual trip with many of them to see Mr. K in Maine. “They send me a card at Father’s Day,” Kanelos says. “My Eagle Scouts, I’m so proud of them.”

Scouting has long been a safe haven for young people struggling to fit in at home or school, says Rick Martin, a longtime Scouting friend of Katon’s who is gay, but wasn’t out when he led her Scout camp in New Hampshire. “You could forget about those other distractions,” says Martin, now chief development officer for Ronald McDonald House New York.

Katon recalls spending hours in the public library over the years, searching for stories of people who felt the way that she did. There wasn’t much: A magazine article about the murder of trans sex workers, an autobiography of trans tennis pro Renée Richards that she read cover to cover in the library, too afraid to check it out. A psychology textbook had a few sentences about “cross-dressers,” who wore women’s clothes, and “transsexuals,” who elected to have surgery. Which of those two categories do I fit into? she wondered.

Katon was about 14 when she learned the truth about her father: He’d left the family because he was gay. He had tried therapy to shed his attraction to men, Katon’s mother explained, but it didn’t take. This put Katon in a panic — she’d thought her need to be a girl would pass. Now she realized it might not.

After the conversation with her mother, “I cried and cried and cried,” Katon recalls. “She thought it was about my dad, but it was about me.”

By her late teens, Katon was in the grips of severe depression. Raised in a Catholic family, she prayed every day to understand why God had selected her to endure what felt like a curse. “I wanted to get rid of this thing so badly,” Katon recalls. Can I just be a girl? Can I just be a guy? she’d think. I don’t care. Pick one and let me be. Plagued by thoughts of suicide, she clung to Scouting, counting down the days until she could be with her troop again.

Before her senior year of high school, in 1985, Katon worked as a counselor at her childhood Boy Scout summer camp in New Hampshire. One night, unable to sleep, Katon slipped out of the tent she shared with Kevin Connolly, her best friend from home. Connolly woke up and found her, and they sat at a picnic table in the dark as Katon tried to explain, for the first time to another person, that she felt she was a girl. Connolly didn’t fully comprehend, he recalls today, but he knew it was big and tried to be supportive. Just knowing Connolly accepted her helped carry Katon through the most difficult years of her life.

Two years later, when Katon was 18, her father died from complications of AIDS. Her family told everyone it was lung cancer. Katon was bereft. She mourned the loss of her father, but also a lost opportunity to connect — maybe they could have talked one day about who they both really were and helped each other? On the day of the funeral, Katon’s friends were working at the Scout camp, and she felt utterly alone.

But when Katon turned to follow her father’s casket out of the church, she was stunned to see rows of pews filled with camp staffers — her people. Rick Martin and others had scrambled to find volunteers to fill in for them at camp, so they could make the drive down to the church in Jamaica Plain and be there to support their friend.

“I was overwhelmed,” Katon would write years later. “Seeing everyone immediately filled my void of pain and loneliness.” It was a kindness she’d never forget.

Katon was standing in line for the cafeteria when she was overcome by a wave of gender dysphoria, the psychological distress caused by a person’s gender identity not aligning with their biological sex. It was January 1989, her first semester at what is now Unity Environmental University in Maine, where she studied outdoor education. Katon was watching an older male student — comfortable, confident, laughing with his friends. He looks so self-assured, so engaged, she thought.

Katon only felt that way as Chuck when she was in “camp mode,” rock climbing or building a fire. But she did feel glimmers of it — that sense of ease, of rightness — when she imagined a different life. In the cafeteria line, she promised herself she’d live as a woman whenever she felt safe doing so.

That Halloween, Katon went to a party wearing a black skirt and a white blouse, her long hair curled and makeup applied by her female friends. Unlike the college guys who dressed as sexy cheerleaders for a laugh, Katon wasn’t in costume — she was revealing a part of who she was. Katon considered herself bigender — sometimes presenting as Chuck, sometimes as Cheryl — and tried to embrace both sides of herself. That Halloween, “I was sharing my other identity,” Katon says, “on the one night a year when I could share myself without fear.”

Back home in the Boston area, Katon was also making her first tentative steps to connect with other trans people, a difficult and dangerous endeavor in the days before the internet at a time when violence was growing, culminating in the murders of several local trans women in the mid-1990s. When she saw an ad in The Boston Phoenix for Vernon’s, a boutique selling size 14WW women’s shoes, she realized That’s code. That’s for me.

Katon spent an hour walking around the store on Moody Street in Waltham, nervous and wondering if she was allowed to try on the dresses. She didn’t dare. But she came back, and the shopkeeper struck up a conversation. That day, the Boston transgender community began to open up.

It was from the shopkeeper that she learned about the Tiffany Club, an invitation-only support group for trans women founded in 1978 and now known as the Trans Community of New England, or TCNE. Club members had designed strict safety measures. On a Tuesday night, Katon was instructed to go to a certain phone booth dressed as Chuck, peppered with questions over the phone, then told to get into a car in the nearby parking lot for an in-person interview. After that, she was invited to follow her interviewers to a house at the end of a cul-de-sac. People who were transitioning lived on the third floor; down below, members played bridge in the kitchen; the basement provided a dedicated space for members to change their clothes and put on makeup. Although Katon wouldn’t join for years — as a college student, she couldn’t afford the $150 annual membership fee — she had unlocked the door to a life she knew she was meant to be living.

Back at college, Katon started dating a young woman named Jenn, a Cambridge native and a childhood friend of one of Katon’s classmates. Jenn already knew about Katon’s identity, and was comfortable with it. “We mostly presented as a hetero-normative cis couple,” Jenn says. But they occasionally went out with a small group of trusted friends as Jenn and Cheryl. “Cheryl was more nervous than I was,” Jenn says.

The couple married in 1993, the year after Katon’s college graduation. At a ceremony with friends and family — Kevin Connolly was best man — Katon wore a tuxedo, Jenn, a wedding dress. A few years later, they renewed their vows in a more private ceremony as Jenn and Cheryl, this time with Katon in a long silver dress and Jenn wearing a women’s suit, their hands bound together in a pagan ritual. “It was a beautiful day,” Jenn says. “This day of our authentic selves.”

Katon had always dreamed of a career with the Boy Scouts — there was no Plan B. After a short stint as an independent contractor, she was hired as a full-time employee in 1993. Her subsequent climb up the corporate ladder took her and Jenn around the Northeast, from New York to New Hampshire to Philadelphia. In 2010, Katon returned to Massachusetts to lead the Boston-area council. It merged with another chapter in 2015 to form the Spirit of Adventure Council, with Katon at the helm.

But Katon had joined the organization in a time of crisis. The Boy Scouts of America was a fairly forward-thinking organization when it was founded in 1910, Katon says. It put children at the center, bucking the mentality that young people should be “seen but not heard.” But its roots were socially conservative and religious, with “duty to God” central to the Boy Scout oath. Churches — especially Mormon, Catholic, and Southern Baptist — chartered most of its members. A 2000 Supreme Court decision had upheld a Scouts’ rule explicitly barring LGBTQ+ members.

By that point, the organization had taken a “hard-right turn” politically, says Rick Martin, the former Scout camp director. Katon describes it more bluntly, as “a progressive organization taken over by knuckleheads.” In her view, the BSA was more motivated by maintaining the status quo, and its traditional relationship with churches — even as the Scouts’ membership and relevance waned — than keeping gay members out.

However, the fight over gay Scouts was far from the biggest crisis unfolding in that era. Past allegations of child sexual abuse, and the Scouts’ mishandling of those reports, had started coming to light. By the time Katon started in Boston, stronger youth protections had been put in place, including criminal background checks for every volunteer. But in years past, allegations of sexual abuse had often been swept under the rug.

The Scouts had kept records of employees and volunteers who had been kicked out of the organization for suspected sexual abuse, but didn’t necessarily report them to the police. In 2012, the Los Angeles Times published a database of roughly 5,000 men, and a few women, who had been quietly expelled from the Scouts in previous decades for alleged sexual abuse. Eventually, some 80,000 former Scouts would come forward to say they were abused. The organization would later enter bankruptcy, and create a $2.46 billion settlement fund for victims, the largest such fund in US history.

In Greater Boston in the 2010s, Katon found a local organization swimming in debt. Membership was dropping, as it was across the country. And local councils were selling some of the estimated 2,000 properties they owned nationwide, worth more than $8 billion. The Boston council had closed a camp in New Hampshire, and had unsuccessfully tried to sell a 112-acre property in Milton where troops often camped on weekends. It was in disrepair and the pool, built just four years earlier, was already closed because of high maintenance costs.

Under the umbrella of the Boy Scouts of America, individual Scouting councils are given wide latitude to make local changes. With this leeway, Katon set out to revive the Milton site. She rebranded it as New England Base Camp, making it a year-round camp open to the public with a high-ropes course, swimming lessons, and refurbished cabins. Her changes attracted non-Scouts, and today about three-quarters of those who use the facility are from outside the organization, such as the school groups that come for team-building exercises or the Islamic Society of Boston, which visits several times a year. The Base Camp brings in $1.7 million a year in revenue, and there are now similar camps in Rhode Island and New Hampshire, with more in the works.

Individual troops have historically also been able to set their own membership rules, and Katon wanted the Boston-area troops to be as inclusive and community-minded as possible. She’d always seen the Scouts’ mission as a very simple one: helping parents work together to raise each other’s kids. She revived the council’s scholarship fund for campers from low-income communities, and provided a Scouting family living in a shelter a place to stay at summer camps in New Hampshire. She also helped the family find a co-ed troop — before girls were officially allowed — and the mother, Lizbeth Valerio-Green, went on to become the troop’s scoutmaster. Two of her children are now Eagle Scouts. Valerio-Green, an immigrant from Costa Rica, says her family’s dedication to Scouting was strengthened by Katon “bringing some light in those darker times.”

Katon’s changes were bringing in new funders and new members. But some longtimers, it would turn out, were highly resistant to change.

Scouts tend to have strong attachments to their camps. Remaking the Milton camp as a profit-making public space meant Scouts no longer had unfettered access to it. Summer camps have even more meaning. As kids, Scouts may attend the same one every summer, returning to work there as teens. Later, they return with their children’s troops.

So Katon’s decision in 2019 to stop operating the Boston council’s T.L. Storer summer camp in Barnstead, New Hampshire — renting out the property to school groups on weekdays instead — struck a nerve. “There’s an emotional investment in the summer camp that you go to. There’s a legacy there,” says Steve Sookikian, 65, an Eagle Scout and longtime volunteer. “People weren’t happy because they were losing something that meant something to them.”

Many in the Scouting community, Katon included, had attended T.L. Storer as children, sleeping at the same campsites, swimming in the ponds, and singing songs in the mess hall. “There’s a lot of longtime Scout volunteers that liked it just the way it was,” says Michael Jeans, a Boston council board member and advisory committee chairman. Adds board member Jeff Reynolds: “Chuck Eaton was a pretty polarizing person within the Scouting community.”

As pressure grew on the national organization to admit gay members, including from local United Way chapters that had withdrawn their financial support, a number of local councils adopted unofficial “don’t ask, don’t tell” policies banning discrimination against gay troop members and leaders. When Boston’s longstanding open-door policy was mentioned in a 2012 Wall Street Journal article, it caught the attention of then-BSA chief executive Wayne Brock.

Although they were on opposite sides of the issue at the time, Katon and Brock started talking every month or so. The BSA had always been a hands-off organization that let parents and young adults lead, she said. Katon argued that by keeping gay people out, the Scouts were breaking their own membership standards that let local troops choose their members and leaders.

Brock listened, Katon says. (Brock, who retired in 2015, did not respond to interview requests.) In early 2013, the Scouts held a national meeting in Dallas to discuss policies regarding LGBTQ+ people with the leaders of the country’s roughly 250 councils. Brock asked Katon to speak first. The following month, hundreds of delegates representing each council voted to allow gay youth to join the Scouts. Two years later, the Scouts started allowing gay leaders and the policy including transgender people followed. By 2019, it had welcomed girls into its flagship programs.

Katon had told a few of her closest colleagues that she was trans. And in 2015, Brock somehow found out. At the end of an unrelated phone call, he asked her bluntly if she had been wearing women’s clothes. Katon admitted it was true, but wished she could have replied with an Eddie Izzard joke: “As a matter of fact, I was wearing my clothes. But yes, I did buy them in the women’s department.”

After several tense conversations, in which Katon assured him she kept her lives separate, Brock allowed her to stay. But Katon still remembers the way he phrased it: Don’t embarrass us.

Katon had planned to continue her bigender existence forever. It seemed like the only way she could keep working for the Boy Scouts. This is fine, she thought. It’s working.

Chuck had essentially become her persona at work. Katon’s kids, who are now in their 20s, knew about Cheryl, as did her church community. Katon didn’t put on her wig and makeup when she mowed the lawn or cleaned the house, but she did when she left for an event. Jenn liked to call her “a lady who lunches.”

Katon was becoming a prominent member of the local LGBTQ+ community. She joined the board of TCNE in 2018, and effectively served as the face of the organization, giving speeches, holding fund-raisers, and organizing volunteer events at nonprofits like the Greater Boston Food Bank and Cradles to Crayons. In 2020, she oversaw an annual conference that attracted more than 1,500 attendees to the Boston Park Plaza.

Even as Cheryl’s profile was rising in the trans community, the animosity toward Chuck from some members of the Scouting community was coming to a head. Anonymous emails were sent to the board and the national leadership team, levying a string of false allegations against Katon: driving drunk, misappropriating funds, and providing alcohol to underage youth. Katon — pained that her efforts to make Scouting a better place for everyone clearly had the opposite effect on some members — vigorously denied all of it.

The local and national councils conducted investigations, and both cleared her name, says Jeans, the Boston council board member. Looking back, Jeans believes the accusations were retaliation by a small group of longtime members upset over the changes Katon ushered in.

Several of those anonymous emails, in the fall of 2018, instructed Katon to come up with an “exit strategy” and announce it by October 15. By this point, Katon was well aware of the people who disliked her, and wasn’t particularly concerned; she tried to forget about it. But on the morning of October 16, she arrived at work in Milton to find her old company car, which she had stopped using, charred and still smoldering. Someone had set it on fire. (A report by a Milton police detective noted that “no evidence has been discovered that would identify a suspect.”)

Around the same time, someone in the Scout community started sending Katon increasingly menacing messages, she says, culminating in a threat to cut off her male genitalia and out her as transgender. With threats rolling in — and fearing for Jenn and their children’s safety — Katon decided it was time to make a change.

I can’t deal with this anymore, she thought. Let me live my life.

The thing she had kept tight grips on for so long was no longer in Katon’s control, and people close to her could see the toll it was taking. Jeans, the board member, says Katon was instrumental in moving the Scouts into the 21st century, and yet “she increasingly realized that being a trans person in Scouting is like pushing water uphill with a broom.”

Her work had been the only thing standing in the way of living as Cheryl full time. If she was going to be outed and forced to resign, she figured, she might as well fully transition. In February 2020, she took her first hormone replacement therapy shot and started looking for a new job.

Katon is now vice president of resource development and donor engagement at Fenway Health, the largest provider of transgender health care in New England. As the only trans person on the organization’s leadership committee, she often speaks publicly about the trans experience, including her own. Candice St. James, a transgender woman who worked with Katon as a fund-raiser for TCNE, says visibility like this is essential. “The people that accept trans people are people who know trans people.”

Katon also serves as an unofficial trans ambassador, knowing her phone will light up whenever attacks are made on trans rights. And with hundreds of anti-trans bills filed across the country this year — seeking bans on youth medical care, books about trans people in school libraries, and more — these calls keep coming.

When she resigned from the Spirit of Adventure Council in early 2021, Jeff Reynolds, the board president at the time, called each member of the 25-person board to tell them about Cheryl. “Almost to a person,” he recalls, “everybody was asking, ‘Does she want to go . . . or can we keep her?’”

For all that’s changed for Katon, a lot has stayed blissfully the same. Kevin Connolly, Katon’s longtime Scout camp tentmate, acknowledges that her transition was a big deal among their mutual friends from Quincy. It sometimes feels as if he’s missing a friend. “I have lost Chuck,” admits Connolly, a retired police officer. “It’s not the same. It’s just not.” And yet they still reminisce about Scout camp, and laugh, and talk about their wives and kids like they always did.

People often ask Jenn if she mourns the loss of her husband. Like Connolly, she does — in a way. Cheryl and Chuck were so compartmentalized she almost feels that one of her partners is gone. But the question irritates her, too: “If you think a person is what they’re wearing or how they look, that’s kind of nuts.”

As for Katon, she says that by going through life as two genders, she’s come to understand how two seemingly opposite things can be true at the same time. How the Scouts could be a conservative institution that led to great pain in her life, while also being a bedrock of strength and support when she needed it most.

“Cheryl Katon’s journey exhibits the courage exemplified in Scouting and we are appreciative of her years of professional leadership,” a representative of the Boy Scouts of America says in a statement. “Cheryl is a living example of the service and leadership Scouting can provide by and to people of different beliefs, backgrounds and experiences. Her impact on the Scouting movement is an important moment in our history.”

Katon is grateful to still be involved in the Scouts. She was recently asked to speak at a virtual Pride celebration organized by the LGBTQ+ employee resource group. Reynolds and other Scout leaders were there to support Katon at a TCNE event honoring her community leadership. Last year, a council in Portland, Oregon, hired the Scouts’ first openly gay CEO. In July, the Scouts dedicated a space for LGBTQ+ youth at its National Jamboree in West Virginia (Katon helped fund-raise for it). She’s hopeful doors will keep opening.

She caught a glimpse of what her life could have been during her last month with the Scouts. When she made it clear she wouldn’t reconsider resigning, the executive board in Boston said she could finish her tenure as Cheryl. In those 30 final, glorious days, Katon got to make several appearances in Zoom meetings and at Boy Scout functions in long hair, makeup, and colorful blouses. She got to hear her colleagues call her “Cheryl” for the first time.

It’s a relief to no longer be living two lives. But Katon doesn’t regret what she’s been through. “I get to live these wonderful chapters,” she says. “I’m so lucky that I have all this richness in my life.”

Katie Johnston can be reached at [email protected]. Follow her @ktkjohnston.