In 2012, when a young New Yorker named Phillip Ensler asked Teach for America—a national, nonprofit program that dispatches teachers to under-resourced schools—to send him to Montgomery, Alabama, his father was not pleased. “My dad’s immediate thought was of civil rights workers Andrew Goodman and Michael Schwerner,” he recalled. The pair, both Jews from New York, along with James Chaney, who was African American, were kidnapped and murdered in Philadelphia, Mississippi, in the summer of 1964.
“He was very worried and nervous about a Jewish boy from New York coming to Montgomery, especially to be involved in social justice work,” Ensler said in a Forward interview.
Ensler understood his father’s concerns but assured him they were long outdated. Ten years later, at the age of 32, he is playing a key role in the state’s Jewish life as executive director of the Jewish Federation of Central Alabama and knocking on doors in search of support as a Talmud-quoting Democratic candidate for the state House of Representatives.
Even more surprisingly, political observers in Alabama think Ensler has a fighting chance to win, which would make him the only Jew in the legislature.
According to the Montgomery Advertiser, the capital city’s daily newspaper, his race is “the only competitive legislative contest in the county” and “represents the Democrats’ best chance to flip a House seat in November.”
Dan Puckett, a Troy University professor who specializes in Southern Jewish history and the Jewish community of Alabama, agrees. Because of redistricting by the legislature in 2021, District 74 has gone from a Republican stronghold to a district that Democrats could possibly take, Puckett says. It is now 55 percent African American by population. Geographically, the district consists of Central Montgomery, parts of Southern Montgomery and a little bit of the North Side. (The U.S. Supreme Court is now hearing a challenge to the state’s redistricting plan, which charges that it dilutes Black representation under the Voting Rights Act. A ruling is unlikely before the November general election).
While an uphill climb, Ensler’s is not a symbolic, kamikaze campaign. But to win, Ensler will need to put together a coalition of African Americans, the few Jewish residents of the district, moderately liberal whites and labor activists, as well as independents—and then get them to turn out.
“Phil Ensler is young, charismatic, and has been a tireless advocate for the Montgomery community,” Puckett says. “He’s brought the same energy to his campaign as he has every other endeavor he’s undertaken. He has a real shot at being elected. Generally, people vote for the “R” or the “D” beside the candidate’s name. But for the few who don’t vote that way, Phil has considerable crossover appeal.”
Ensler’s GOP opponent is Charlotte Meadows, who was first elected to the seat in 2018, after serving on the county board of education. She ticks all the boxes of a deep red state representative: she opposes abortion without exception and she prefers state support for charter schools (she is on the board of one) and vouchers, rather than traditional public schools. She also voted for a new law allowing for the carrying of firearms, anywhere, without a permit. Meadows has raised $500,000 for her campaign, half of it from PACs. Ensler has generated a lower, but still robust, campaign budget of $300,000. With the help of young campaign volunteers, including some who were his students at a local high school while he was with Teach for America, Ensler is methodically knocking on doors in neighborhoods across his district.
On a late afternoon in October, Ensler meets up with two of the young volunteers, both products of Montgomery’s public school system, and both on break from Morehouse University, in the parking lot of a credit union. Ensler, 32, is dressed in a navy campaign T-shirt with his name and district stenciled in white letters, New Balance sneakers and a water bottle stuffed into the back pocket of his worn blue jeans. His full head of jet-black hair is swept back from his forehead, a stylish stubble completing the Millennial ensemble.
The pre-canvass briefing takes place next to Ensler’s white Ford SUV with campaign posters on the front doors. Ensler reviews the app that gives volunteers the addresses in the neighborhood where supportive or persuadable voters live. The three then divide up the targets.
The Brentwood neighborhood being canvassed this afternoon is moderately prosperous and middle-class. It is racially mixed, with mostly one-story brick ramblers, fronted by generous, well-manicured lawns and occasional cul-de-sacs. On doorsteps, Ensler is low-key and affable as he hands out one-page campaign fliers and touches on the main points of his campaign: public safety and “common-sense policies that reduce gun violence.” He makes no mention of regulating assault weapons or gun control, but, citing opposition by the Alabama Sheriffs Association, he decries the new “permitless carry” law his opponent supports. Instead, he told one interviewer that he wants to “empower law enforcement to be able to identify who may be a threat or who may be up to no good.” Other issues named on the flier are education, economic opportunities and healthcare.
While Ensler is strongly pro-choice, his flier makes no mention of reproductive rights. The flyer describes Ensler as “a servant leader,” revealing a savvy approach to regional religious sensibilities. The phrase is a term of art, a construction easily recognizable to Christians, especially evangelicals, both White and Black.
Ensler shakes hands with President Obama in the Oval Office.
While in college, Ensler visited some of the civil rights museums in Montgomery, which helped ignite his political engagement. “I was humbled and inspired by standing in the very places where Martin Luther King Jr., John Lewis, Rosa Parks and countless other heroes and foot soldiers had the courage to stand up for a more just and equal Alabama,” he writes on his website.
Ensler worked for New York’s governor David Paterson, that state’s first Black chief executive, in high school, and then during summer break in college. He became a White House intern in college and was then promoted to support staff in the Obama administration. There he worked in the office of Reggie Love, Obama’s personal assistant and “body man.” After graduating in 2012, Ensler joined Teach for America, where he taught social studies at the predominately Black Robert E. Lee High School in Montgomery.
That same year, he founded an organization called Marching On, a week-long program in which he would take as many as 70 students to Washington, D.C. to meet with government and policy officials, as well as to visit local universities and cultural institutions. The program ultimately included students from all five of the city’s public high schools. Ensler still runs it.
But after two years with Teach for America, Ensler concluded that he could make more of a difference as a lawyer. So, in 2014, he enrolled in Cardozo Law School, which is affiliated with Yeshiva University. While in law school, Ensler interned with the Southern Poverty Law Center in Montgomery, Project Innocence, and again in the office of New York Governor Paterson.
In 2017, he joined the Alabama Appleseed Center for Law and Justice, a progressive civil rights think tank that focused on criminal justice reform. In 2020, Ensler went to work for Montgomery Mayor Steven Reed. In 2019, Ensler was the subject of a flattering Advertiser profile, which named him its monthly “Community Hero.”
“At an intersection of politics, education and legal defense,” the newspaper wrote, “Ensler is an advocate for those in need. He breaks barriers for low-income people with no access to a lawyer and pushes for criminal justice reform. He’s helped organize a community reconciliation project to honor lynching victims. And, for eight years, Ensler has brought hope to underprivileged students in Montgomery by introducing them to powerful people in the White House, and across Washington, with similar stories.”
Ensler is most proud of being part of the legal team that recently represented Claudette Colvin, an unsung Civil Rights activist who was arrested for refusing to give up her bus seat to a white woman in Montgomery almost a year before Rosa Parks, but who was deemed a problematic symbol by the NAACP. Now 82, in 2021 the record of her arrest was expunged with the Ensler’s help.
In his run for the legislature, Ensler may hope to echo the early years of Jay Rockefeller IV, who was assigned to West Virginia while serving in VISTA (Volunteers in Service to America) in the early 1960s. When his term as a volunteer was up, the scion ran, successfully, for the West Virginia legislature, and began a long political climb to become the state’s governor and then U.S. Senator.
But for now, at least, Ensler’s sights are focused on his statehouse race. And he is clear-eyed about what may be ahead of him if he does win in November; Democrats are vastly outnumbered by Republicans in both houses of the Alabama legislature.
Ensler stands with Montgomery high school students on a trip to Washington DC.
Judaism was front and center in the Ensler family’s life and has remained so. Phillip and his twin sister Caroline attended Hebrew School at Manhattan’s Central Synagogue, a Reform congregation on the East Side, where they had their joint b’nai mitzvot, and spent summers at Jewish camps. The family made two trips to Israel when the children were younger, and Ensler later went on a Birthright trip while an undergraduate at George Washington University.
“I felt very connected to Jewish religion and, and spirituality,” he says, saying Birthright “made me that much more proud of my Jewish identity.”
These days, Ensler is a member of Agudath Israel/Agudath Israel Etz Ahayem, Montgomery’s main Conservative/Sephardi synagogue, but he is careful to make holiday appearances at Beth Or, the Reform synagogue. Although a relative newcomer to Montgomery, he said that he had been embraced like a son by the Jewish community. As executive director of the Jewish Federation of Central Alabama, Ensler says he has led efforts “to combat antisemitism and build multi-faith coalitions to combat racism and foster acceptance of all people.”
Ensler has repeated this commitment during the current campaign, which has thus far been unmarred by antisemitism.
“The Jewish community is very supportive of me,” he says, pointing to the fact that he hasn’t been asked to step down from his day job leading the Federation during the campaign. “They want me to win.”
Much of Ensler’s political and financial support, he says, has come from his family and friends, as well as Jewish donors inside and outside his district. One of Ensler’s supporters is Joe Levin, cofounder of the Montgomery-based Southern Poverty Law Center, who first met Ensler when the younger man was a senior policy adviser to Steven L. Reed, the city’s first African American mayor.
“His concerns were the rise in white supremacism and antisemitism,” Levin says. “His history of working for nonprofits that support justice and equality are consistent with all that he would do in Alabama’s legislature. How could I not support him?”
Durham-based journalist and author Mark I. Pinsky has covered Southern politics for numerous publications and platforms since 1972.
Top photo: (L to R), Phil Ensler, volunteers Aylon Gipson, Andarious Porter. Photo by Mark I. Pinsky.