Ben Strauss is the co-author of Indentured: The Inside Story of the Rebellion Against the NCAA, winner of the 2017 PEN/ESPN award for literary sports writing.

BOSTON — On the morning of October 20, a Facebook Group called “Originally from Oak Square Brighton” was in an uproar. Typically, the several hundred members share childhood memories from their Boston neighborhood or news that an old friend has passed away. But on this night, they were grappling with a segment that had aired the night before on Lawrence O’Donnell’s MSNBC show. O’Donnell had dedicated his opening monologue to a takedown of John Kelly, President Donald Trump’s chief of staff. Kelly had spoken in the White House briefing room about losing his son Robert to a roadside bomb in Afghanistan, as part of an effort to calm a dustup over a condolence call between his boss and the mother of a soldier killed in Niger. Congresswoman Frederica Wilson, an African-American Democrat from Florida, had listened to the call and publicly questioned Trump’s lack of empathy; Kelly hadn’t exactly defused the situation when he fired back, calling Wilson an “empty barrel.”

O’Donnell had a simple explanation for Kelly’s personal attack: his Boston roots. Specifically, it was the neighborhood where he grew up, Oak Square, an Irish-Catholic pocket of the Brighton neighborhood, located on the western edge of the city. “I know the neighborhood John Kelly comes from,” O’Donnell, who grew up in nearby Dorchester and went to high school in Oak Square, had said. “I know the culture.” He continued, painting Kelly and his neighborhood with the worst of Boston’s stereotypes: “It was a neighborhood in which calling someone who looked like Frederica Wilson an empty barrel was the kindest thing that would have been said about her.”


On Facebook, the dozens of responses to the video clip revealed a split among Oak Square natives. “Thought it was a perfect narrative by Lawrence O’Donnell,” one comment read. “Growing up in Oak Square was a great place to live. No (Racism) here,” wrote another. Pulsing through the debate, though, was a palpable sense of anger. As Kelly’s childhood friend Dave Wright put it to me, “Lawrence is full of shit, he’s from the whitest enclave in Boston! Maybe he got beat up by some Oak Square kids on his way to school.”

Kelly, 67, has been Trump’s chief of staff for eight months now, and there is no debate among former and current residents that the conflicting views of him and his role in this most unorthodox White House—he’s Trump’s order-enforcing traffic cop; he quietly encourages Trump’s most hard-line views on immigration—have their roots in Oak Square. In the 1960s, Oak Square and the surrounding Brighton area created an unusual mixture of New England liberalism and a blue-collar nativism. The hierarchies of the Catholic Church and the military were revered institutions in Oak Square, but there was spillover from Boston University and Boston College, which weren’t far away. To the extent that Oak Square made Kelly the man he is today, it tugged him in two main directions: The traditionalist who reveres the military and rhapsodizes from the White House podium about how “women were sacred” when he was growing up, and the hardened bureaucrat who may harbor few prejudices of his own, but doesn’t flinch at working for a president who denigrates immigrants and minorities.

Despite the images O’Donnell aired on his show of rocks being thrown at buses during Boston’s infamous effort to desegregate its public schools, the public high school in Kelly’s neighborhood was far more welcoming of black students and never experienced the worst of the desegregation violence that plagued South Boston, on the other side of the city. But it wasn’t without its bias. During a mayoral election that featured a race-baiting candidate in 1967, Kelly’s neighborhood of Oak Square was split almost exactly 50-50. Among some former and current residents, when Kelly calls a black congresswoman “an empty barrel” or says immigrants who didn’t apply for the Deferred Action for Childhood Arrivals program “were too lazy to get off their asses,” they recognize strains of the old neighborhood.

Watching the Trump administration careen from controversy to controversy—the aftermath of the Charlottesville rally to the president’s reprise this week of his infamous Mexican criminals line—and Kelly’s role in it has caused some soul-searching for many of them. Several pointed out to me that Joe Kennedy III, the Democratic congressman who delivered the rebuttal to Trump’s State of the Union this year, grew up in the house next door to where Kelly was raised, albeit some years later. “We have a mix of people from the neighborhood who are conservative and people who are liberal,” Charlie Vasiliades, a 60-year-old lifetime resident of the neighborhood told me. “And there are people who are conflicted about John Kelly working for Trump.” Added another older resident of Oak Square, who grew up near Kelly, “I don’t like our community defined by one person. We created this person? That’s not fair to us.”

Though Kelly has been the subject of recent speculation that his job is in jeopardy as his emboldened boss follows his own gut on major White House decisions, he remains one of Trump’s most influential senior staff just by dint of his aggressive enforcement policies during his six-month stint as head of the Department of Homeland Security. During that time, he oversaw a 40-percent increase in arrests of undocumented immigrants by permitting his agents to detain anyone here illegally, rather than just people who had committed serious crimes. Kelly’s response to criticism that his agency’s stepped-up deportations were ripping apart families was curt. “If lawmakers do not like the laws that we enforce, that we are charged to enforce, that we are sworn to enforce, then they should have the courage and the skills to change those laws,” he said at a speech at George Washington University. “Otherwise, they should shut up and support the men and women on the front lines.”

As Trump dispatches National Guard troops to the Mexican border, ratcheting up the heat on the national debate on immigration, the four-star general remains, for all his rumored impatience with his undisciplined boss, one of the president’s most reliable allies on implementing perhaps his most important campaign promise: border security. (Kelly did not comment for this story.) To better understand the place that shaped a young Kelly, I visited Oak Square recently in search of what it was like when Kelly grew up; its values, its character and also what Kelly’s job in the Trump administration means to the neighborhood today. Kelly may have left Oak Square for a career in the military decades ago, but as Leon Panetta, the former secretary of defense and Kelly’s former boss, told me, “John’s a Marine’s Marine, but he’s also a Bostonian’s Bostonian. To know John Kelly is to really know the heart and soul of his Brighton-Oak square roots. That’s where he came from.”

“Immigration is a law-and-order thing for him,” Panetta said. “It’s not that people can’t come here but they’ve got to follow the rules. That’s what he learned growing up.”



***

About a mile from where Kelly grew up is Johnny D’s, a fruit stand that sits underneath a green-and-white-striped awning on Washington Street. In the window, displayed next to a sign that advertises bananas for 69 cents a pound, is a Time magazine cover featuring Kelly. The caption reads, “Trump’s Last Best Hope.” Johnny D’s is an institution in the neighborhood, run by Johnny DePietro, who also happens to be Kelly’s stepbrother (Kelly’s mother died of cancer after he graduated from high school and his father remarried DePietro’s mother). I walked in on a recent afternoon and asked if Johnny D. was free to talk about Kelly. “I hope it’s not too political,” one of the store’s employees said to no one in particular. “We’ll get boycotted.”

In between puffs on a cigarette in the back of the store, Johnny D. later told me how proud he is of his stepbrother. “He’s a neighborhood guy made good, you know?” he said. “There’s a lot of people who hate everything about the Trump organization and everyone connected to them. But if anybody brought any of that stuff up to me, they know I’d cut ’em right off.”

To walk around Oak Square today is to find a neighborhood that has changed in some ways—there’s a pizza joint and a Thai restaurant on the square; Gray’s Market, the old neighborhood grocery, is now a liquor store and nail salon—but has also hung on to much of what made it something of a hidden enclave 60 years ago. The firehouse and library are original buildings that date to the early part of the 20th century. The main square, a small triangular patch of grass that gave the neighborhood its name—it was once home to a giant oak tree—has an aluminum pole that flies an American flag and the black POW-MIA flag that says: “You are not forgotten.”

John Kelly's former home. | Jason Grow for Politico Magazine

Kelly grew up a few blocks from the small park, up the hill on Bigelow Street. His father, John F. Kelly, was of Irish descent; his mother, Josephine “Honey” Pedalino, was the descendant of Italian immigrants (a “mixed marriage,” as John Kelly likes to say). Her father never spoke a word of English and made his living peddling a fruit cart in East Boston. Kelly’s paternal grandfather was a brakeman for the railroad.

When new rail lines were built in Boston, upwardly mobile immigrants left the city’s center and headed west to Brighton and Oak Square. By 1920, Kelly’s father’s family had moved to the neighborhood. He went off to World War II and started a family when he returned. Kelly, born in 1950, was one of five kids.

The block where Kelly grew up included business owners, city workers and a Boston College professor. Neighbors remember the Kellys as a particularly devout Catholic family in a neighborhood where nuns took attendance at Sunday mass at Our Lady of Presentation Church. “If you weren’t there, you better be dead,” one said. Kelly went to Catholic school at Our Lady of Presentation, was a Boy Scout and spent his free time ice skating and playing gin rummy. Friends thought of Kelly as a leader at a young age. Once, when a group tried to build a treehouse with some wood scraps, they began by ripping the nails out of the wood with their bare hands. The next day, Kelly showed up with his father’s hammer. A day later, the whole crew raided their fathers’ toolboxes for their own hammers and the work went much faster.

The deep impressions on Kelly start with his father. First, there was his work ethic: he worked two jobs for four decades, delivering mail during the day and then for the railroad in the evenings. He left the house at 5 in the morning and didn’t return until nearly midnight. A former neighbor of Kelly’s and a Trump voter, Linda Salvucci, told me, “You work or you get outta here—that’s how the neighborhood was. There was no going on welfare.” She added, “It sounds like Kelly is like that, too.”

Bigelow St. circa 1920, looking up from Oak Square; the Kelley home is not visible, but would be about a block beyond the crest of the hill on the right. | Bright-Alston Heritage Museum

Growing up, Kelly spent time on the stoop of his house listening to war stories from his father and his two uncles, Leo and Russell. He has told groups of Marines the impact they had on him, and how they stirred his call to enlist after high school (Kelly also spent time on the stoop listening to Red Sox games and boxing matches featuring Rocky Marciano, who grew up in Brockton, south of Boston.) The Kellys weren’t the only patriotic family in the neighborhood; most households included veterans and many were Gold Star families. During World War II, women cut stars out of fabric and put them in the windows for each member of the house that was away fighting. After the war, the national anthem was sung before kids’ baseball games and there were parades on Memorial and Veterans Day. Chris Daly, a professor at Boston University who studies Boston history, told me, “This is the time and place that Trump is talking about when he talks about making America great again.”

But if there were idyllic qualities of post-war America in Oak Square, there were also shades of bigotry. It was overwhelmingly white and predominantly Irish-Catholic. When an Asian family came to stay at a house in the neighborhood after World War II, residents complained to the host family, according to an account in a neighborhood newspaper years later. One of Kelly’s old neighbors, Paula Samuel, told me that her mother warned her to stay away from the one house in the neighborhood where a black family lived. “She didn’t say it was because they were black, but you got the idea,” Samuel told me.

Nancy Atwood, another former resident of Oak Square recalled that during the mid-60s at Brighton High School, a posse gathered outside the school to protest a black and white couple who planned to attend the prom together. It was indicative, she said, of a duality of the area. “You had black and white kids mixing,” she said, “but then you also had the backlash to it.”



***

Fifty years before Trump was elected president, the 1967 mayoral race in Boston pitted Kevin White, the young secretary of the commonwealth, against Louise Day Hicks, a member of the school board from South Boston. Hicks’ campaign drew its energy from working-class whites and their resentment to the civil rights movement and efforts to desegregate the city. She purposely showed up in neighborhoods where she knew she’d be protested and was nicknamed the Bull Connor of Boston. She’d later be courted by George Wallace as a running mate. When she ran for mayor in 1967 her campaign slogan was a blaring dog whistle, stating simply: “You know where I stand.”

Many of the people I spoke to recalled a hard-fought election that signaled a battle over the soul of the city. Sensing the stakes, the Boston Globe broke with tradition and endorsed White, the first time in decades the paper had picked a candidate. White won the election by 12,000 votes. “It was important because the city decided we’re not going to be the Biloxi, Mississippi of the north,” said Mike McCormack, a former city councilman. How did Oak Square vote? According to data pulled for me by the Boston Public Library, the precincts that encompassed the neighborhood split their vote nearly down the middle: 1,769 votes for Hicks; 1,776 for White.

By the time White was elected mayor, Kelly was commuting to St. Mary’s, a small parochial high school that was a short bus ride away in the suburb of Waltham. He was a class officer, played on the golf team and was a member of the radio club. He graduated in a class of around 60 and his senior yearbook quote was “California or bust.” “It was all about his sense of adventure,” said Peter Muis, one of his high school classmates. Kelly hasn’t lived in Oak Square since he enlisted in the Marines in 1970, but Panetta, the son of Italian immigrants, told me the neighborhood kid in Kelly isn’t hard to find. The two often attended mass when they used to travel together, and Kelly remains devoted to the Red Sox. “We talked a lot about our shared experiences,” Panetta said.

George McCormack bought the house from the Kellys in the 1970. | Jason Grow for Politico Magazine

Kelly also carries another kind of neighborhood scarring with him. During the 1970s, Oak Square became a rendezvous point for the heroin that was coming into Boston from New York City. On the western edge of the city, it was an easy exit off the Massachusetts Turnpike for dealers to make pickups. “Everybody from the rest of the city would meet in Oak Square,” Dave Wright, Kelly’s childhood friend, told me. “Some of it filtered out on the locals. It touched a lot of families. We all knew somebody.” One longtime Oak Square dweller recalled that a neighborhood boy was found dead in a car next to the square after he had overdosed. The square earned the nickname “Needle Park,” because of the drug paraphernalia that littered it for years.

In 2016, Kelly told a reporter from the Defense News that all but one of 25 of his childhood friends had died from alcohol or drugs. While that certainly sounds like an exaggeration, several people told me Kelly has attributed his hard-line stance on drugs to losing friends in Oak Square. (Kelly also lost a brother, Charlie, to AIDS in 2006.)

The house that Kelly grew up in is a large white duplex with a Philadelphia-style design; two separate front doors lead to different apartments. According to the 1960 census, Kelly’s grandmother lived in the house with his family when he was young, and another family, the Meyers, lived in the other apartment. Today, a tattered American flag hangs from an aluminum pole in the front yard. When I knocked on the door on a recent afternoon, I was greeted by a wisp of a man in his 80s named George McCormack. McCormack bought the house from the Kellys in the 1970s and later became friends with Joe Kennedy II, who moved into the large Victorian house next door in the ’80s and represented the district in Congress.

Jason Grow for Politico Magazine

McCormack didn’t remember much about the Kellys, except that he got a great deal on the house. “I paid $20,000,” he said with a grin, before inviting me inside. One living room wall was an homage to a triumvirate of Boston sports heroes: Ted Williams, Bobby Orr and Larry Bird (Williams, when he played for the Red Sox, lived in Brighton). On another wall was a photograph of McCormack’s brother and the Gold Star he was awarded during World War II. McCormack fought in Korea and worked as a mechanic most of his life. He raised the pole in the front yard some years ago. He showed me the house’s big backyard and told me his daughter now lives in the apartment upstairs. “It was a good place to raise a family,” he said.

On the bookshelf in his living room was a copy of Hillary Clinton’s memoir, “Hard Choices.” “I was never a Trump guy” McCormack said. “I thought he’d get shot before he got into office.” Before I left, McCormack made sure to show me the new American flag he hopes to raise to replace the worn one that now waves in his front yard—just as soon as the weather gets warmer. “I’d like Gen. Kelly to come see it,” he said. “He’s a hero of mine.”