Dozens of community members and activists attended a Regional School Unit 24 board meeting in Sullivan last December, the first since the state filed a lawsuit against the district over a resolution aiming to ban transgender students from bathrooms and sports teams that aligned with their gender identity.
After heated public comments, the community waited to see whether the board would drop its policy plans to avoid the lawsuit and still-unknown costs, or push forward with its bid to block transgender inclusion in sports.
Unknown to the public, a conservative activist was texting with one of the board’s most powerful members, encouraging the district to take on the legal fight that some school leaders did not believe they could win.
Moments before the school board planned to meet with its longtime counsel, Portland-based Drummond Woodsum, board member Carla Jung made a motion to exclude the firm and instead consult with Steve Smith Trial Lawyers, a conservative Augusta firm that the school had not yet retained and that had a record of pushing districts to disregard their typical legal advisors. The move sparked debate over procedure, and some board members said in the meeting they were caught off guard because the motion was not on the agenda.
While arguments unfolded, Jung was texting Heidi Sampson, the head of the Maine Education Initiative, part of the conservative Maine Policy Institute, a Maine Monitor analysis of newly released documents shows. Sampson had served as Jung’s confidant and advisor for months and had told Jung about the alternative lawyers in the summer. Her group also provided a sample school policy to Jung that would bar transgender students from certain sports and private spaces. Jung had pushed the policy change through in October, with just four of the board’s nine members supporting the measure.
“They are trying to say it’s not weighted,” Jung texted Sampson during the Dec. 9, 2025, meeting. Jung was referencing the board’s weighted voting system, which gives greater voting power to members from larger towns such as her own. Despite being one of nine people on the board, Jung carried 20.5% of the vote.
“Well, they’d have to prove that to you,” replied Sampson, who is also a former Republican state representative from Alfred. Sampson advised Jung that the vote would be weighted.
Sampson was right. The board voted to exclude Drummond Woodsum from the executive session. Five of the nine school board members opposed the move, but their votes did not carry enough weight to block the decision.
Board members decided to push forward with the policy and hire Steve Smith Trial Lawyers, which has gone on to defend the district against the state in court. Drummond Woodsum, by contrast, had advised other school districts to follow state law.
Sampson’s group, as well as the Maine First Project, run by Republican former state Rep. Larry Lockman, and a local chapter of the national organization Parents’ Rights in Education, have been actively working to get conservative school board members elected across the state and to train them to pass policies that align with their values.
They jumped at the chance to push transgender students — a small demographic in Maine — out of teams, locker rooms and bathrooms aligning with their gender identity after an executive order by President Donald Trump claimed that Title IX, a landmark women’s rights statute, required separation by biological sex.
More than 900 pages of documents recently released by a group of area residents reveal the extent of Jung’s communication with Sampson and the influence conservative policy groups had on the district’s debate over transgender rights policy. They also show that board members discussed whether they could fire the superintendent if he refused to enforce the new rules and that Jung at one point asked for details from an individual student’s birth certificate.
The texts and emails spanning Jan. 1, 2025, to this summer show the board member from Franklin, who was elected in March 2025 with the support of the Maine First Project, regularly sought advice and support from Sampson and leaders of the two other conservative groups in her push to regulate which sports teams and spaces transgender students use, and persuade others on the board that this was the right course of action.
Along the way, Sampson downplayed the legal risk, telling Jung that the state wouldn’t sue schools that chose to align their policies with the Trump administration’s interpretation of Title IX and that the state even wanted to “return all their policies to reflect biological male and female,” according to an August 2025 email to Jung — statements that turned out to be wrong.
‘Any tool provided’
At least seven districts in Maine have changed their policies to match a Trump administration executive order issued in February 2025 aimed at keeping transgender girls out of girls’ sports. The state is now suing the districts for violating the Maine Human Rights Act, which prohibits discrimination based on gender identity. The Trump administration is also suing Maine for allowing transgender athletes to play on girls’ sports teams.
Not everyone was enthused about switching lawyers or the outside influence. After Sampson told Jung about Steve Smith Trial Lawyers in August 2025, Jung brought up the idea of getting a legal opinion from the firm to two other school board members, chair Jeffrey Alley and Mary Cowperthwaite, in an email. Alley, who had voted against the district’s resolution to align with Trump’s executive order in October, then texted a board member about Jung’s idea.
“She’s going to use every tool provided her by her outside backers to force our hand. I don’t want boys competing against girls, and I don’t want them in girls’ locker rooms, but I also have no desire to create a problem where there isn’t one,” wrote Alley.
The other board member, whose identity is unclear in the messages, agreed.
“I will not vote to support an attorney who does not know school law,” the member texted Alley, relaying concerns of Steve Smith Trial Lawyers’ apparently limited experience with education law. “That is asking us to put our district in legal danger and I cannot support that.”
“I can’t see any reason why we should switch attorneys unless we’re PLANNING to go to court,” Alley texted a couple of weeks later.
Representatives from Steve Smith Trial Lawyers could not be reached for comment.
Two residents, Tammy Taylor and Russ Linton of Mariaville, said the records, which they requested from the district this spring and received in August, confirmed their suspicions that outside actors were influencing the school board’s decisions, especially Jung’s.
“Turned out Carla was not only texting the out-of-town influencers in the audience but also being handled by Heidi Sampson in real time,” Linton told The Monitor. “That’s absolutely wild to me.”
Jung did not respond to four requests for an interview.
In a recent interview with The Monitor, Superintendent Michael Eastman said he was blindsided by the Dec. 9 bid to switch the district’s legal counsel, though he acknowledged board members are allowed to consult with outside sources to do their job. Still, he worries the discord reflects poorly on the district.
“Our reputation’s been clouded by sort of this dissension that exists around this issue when truly we have a lot of people that want nothing but the best for this district,” Eastman said. “They want to do what’s in the best interest of kids and best interest of the district. There are times when our beliefs play into that.”
Sampson, for her part, told The Monitor that school board members frequently consult with groups such as the Maine School Management Association, which represents school boards and superintendents around the state, and others as they make policy decisions. She argued that her group plays a similar role but has a different point of view.
“It’s essentially an echo chamber,” she said, referring to the groups that traditionally advise school board members on policy and procedure. “So I come in and have a different perspective on things, and I don’t think that’s any shock to you or anybody else that knows me.”
‘Unanswered questions’
The anti-transgender perspective pushed by Sampson’s group was clear in Jung’s campaign for the school board last spring. Fliers paid for by the Maine First Project claimed she would advocate for “protecting children from radical transgender ideology” and keeping biological males off girls sports teams and out of girls’ restrooms. To do so, she would need others on the board to agree with her to follow through on those promises.
But while the board narrowly pushed through an agenda that targeted transgender kids with weighted votes, messages show there was tension about how to enforce the policy — if at all — behind the scenes. Much of the debate centered on the power of Trump’s executive order versus state law, and the position the policy would put school administrators in.
At one point, Eastman weighed ignoring the new directive and instead continuing to follow state law.
“I’ve been contemplating calling a meeting. Telling them we have a trans [sic] who uses the other bathroom and asking them how they think I should handle it,” Eastman texted a board member in an undated message. “And then tell them that I will not write them up as it is not illegal. And then say how do you like them apples??? What do you think?”
Eastman later told The Monitor that this message was an atypical emotional response to the tense debate that was unfolding in his district. However, he said that there was a level of uncertainty that made it difficult to move the district forward under the new policy, which is at odds with state law.
“I like black and white. To me, the law was black and white,” Eastman said.
And while Alley and some other school board members appeared to support the restrictions in principle, the texts and emails show they did not want to put the district’s staff at risk of legal action for violating state law. They also wondered what would happen if staff refused to follow the board’s directive.
“If Mike [Eastman] refuses to violate state law by ordering an admin to enforce Title IX, thereby denying locker room access to a trans woman, are we firing Mike? Likewise if he orders an admin to follow our resolution and they refuse, on the grounds that it’s a violation of state law, are we firing the admin?” Alley, the school board chair, texted an unidentified person on Oct. 8, just one day after the board voted in favor of aligning with the Trump administration on Title IX.
Alley declined an interview with The Monitor and directed questions to the superintendent.
For Sampson, the answer was clear.
“The board has voted accordingly and whether they sign it or not, it is now a policy and needs to be followed,” Sampson wrote in an undated message to an unidentified board member. “Now you have a superintendent who is being insubordinate to the board[.] You can fire a superintendent for being insubordinate.”
Allen Sarvinas, with Parents’ Rights in Education, emailed the board before its Dec. 9 meeting to express a similar sentiment.
“If I told my boss to go fly a kite and refused to do my job, I would be fired. Why is the Superintendent allowed to refuse the board’s decision, which essentially undermines the will of the people? What happened to preserving democracy?” he wrote.
It was unclear exactly how Sarvinas knew of Eastman’s opposition to the policy. In an email to Eastman, school board member Jennifer DesJardin wrote that the “only way this person would know that you said you wouldn’t do this is if someone talked about on of [sic] our executive sessions.”
Executive sessions are confidential by law.
Eastman told The Monitor he was not surprised by what he saw when skimming through the documents. He had also had conversations with the board chair about what could happen if he refused to follow the new policy.
“I didn’t feel threatened,” Eastman said.
Alley questioned whether the board could face legal repercussions if it enforced the new policy.
“There’s a reasonable question to be asked about whether or not the BOARD is protected from legal liability if we DIRECT employees to break the law,” Alley wrote in an undated message. “This is not some clear cut case of right vs wrong, there are unanswered questions.”
One question that remained unanswered about the district’s liability was whether or not there were transgender students in the district who might take action against the district for violating their rights under state law. Much of the conversation in the texts and emails appears to be centered on hypothetical scenarios, but in one email exchange, Jung asked Eastman to disclose the sex on the birth certificate of a specific student.
“[T]he child is listed as male or female?” Jung asked Eastman on Dec. 4.
Eastman told The Monitor that he did not discuss an individual student.
‘The long haul’
The policy separating facilities by biological sex as determined at birth took effect on July 1. So far, Eastman said he has not needed to enforce it. The plan is to handle any case that arises individually, he said, as school leaders do with other issues.
In the meantime, some in the district would like to see the board change the way power is divided among members. More than 400 people signed a petition asking the RSU 24 board to reconsider how it weighs votes, according to The Ellsworth American.
But the board rejected a proposal to consider doing so at its meeting earlier this month. They used the weighted vote system in which four board members — Jung, Garnett, Cowperthwaite and Mercy Hardison, who account for more than 62% of the vote — said no to forming a committee to look at reapportioning the board’s votes.
Eastman said that the district needs to focus on moving forward after a divisive year, though that will be tricky as the debate over Title IX continues to play out on the local and national stage.
Some conservatives had hoped the U.S. Supreme Court would weigh in on whether Title IX prohibits transgender athletes from competing in girls sports, but, in a 6-3 decision in June, the court largely left the question of whether to separate sports teams by biological sex to the states.
As Maine’s lawsuit against school districts continues, some are seeking to force Mainers to vote on the issue. After the secretary of state’s office struck down a proposed ballot question on transgender athletes in school sports, petitioners are working to get the question before voters in 2027.
“I think we’re in for the long haul,” Eastman said.