MEDFORD — When Dorothy Rubin Schepps thinks of Michael Bloomberg, the billionaire media mogul and former New York City mayor, her mind always goes back to her honors literature class with Ms. Kathleen Sharkey, senior year at Medford High School.
The class was assigned a research paper and her classmate, a young Bloomberg, wrote about a discredited conspiracy theory that President Franklin D. Roosevelt knew the Japanese planned to attack Pearl Harbor and allowed it to happen to galvanize support for war with Nazi Germany. As Schepps recalled, Bloomberg’s assignment rattled Sharkey, a notoriously tough teacher who adored Roosevelt and suffered no fools.
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"Bloomberg, I’m not even going to read this paper,” she snapped as she threw it back at him. Undeterred, he submitted the paper to his honors history teacher, according to a 2009 biography. Bloomberg got an “A.”
“Even at 18, Michael was thinking outside the box," said Schepps, 77, who counts herself among Bloomberg’s supporters in the heated Democratic presidential primary. "We realized in retrospect that he was smarter than Medford High.”
Six decades later, Bloomberg, 78, finds himself in the thick of the race for the nomination, thanks in part to his staggering wealth — estimated by Forbes at more than $60 billion — which has allowed him to flood the airwaves with campaign advertisements despite being one of the last entrants into a crowded field.
As he did with his high school essay, Bloomberg is running a campaign that is trying to rattle and, perhaps, outsmart the political establishment, potentially upending the way presidential nominees have been picked for the past half-century.
When he entered the race in the late fall, Bloomberg said he didn’t have enough time to compete in the first four states — Iowa, New Hampshire, Nevada, and South Carolina. Since 1972, no one in either party has become the nominee without doing well in Iowa and New Hampshire. Yet Bloomberg has argued that he can pull it off, in part because he’s willing to personally bankroll his campaign with hundreds of millions of dollars to disrupt what remains of a large and unsettled Democratic field.
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However, as his first presidential debate demonstrated, his opponents appear all too happy to use him as a foil. A former Republican, Bloomberg has cut a controversial figure, laden with political and personal baggage that his rivals have been eager to assail. During his tenure as mayor from 2002 to 2013, he embraced stop-and-frisk, an aggressive policing tactic that disproportionately subjected millions of Black and Latino men to unwarranted searches. He also faces renewed scrutiny over allegations that he sexually harassed and discriminated against women at the company he founded.
To change the narrative, Bloomberg is expected to play up his bootstrap roots in the final stretch before Super Tuesday, March 3, when Massachusetts and 13 other delegate-rich states, including California and Texas, will hold their presidential primaries. In a campaign video, released earlier this month and filmed late last year in front of the chartreuse walls of his childhood home in Medford, Bloomberg touted his middle-class bona fides: shoveling snow in the winter and mowing lawns for pocket money.
“He is genuinely a self-made billionaire,” Schepps said. "I don’t care if he buys [the election]. . . . For me, he’s on the correct side of the issues I care about: climate change and gun control and so many other issues. And I think fundamentally, he’s not corrupt. He’s not a swamp creature and I know where he comes from and he comes from good values.”
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In school, bright but bored
Michael Bloomberg was born on Valentine’s Day in 1942 at St. Elizabeth’s Hospital in Brighton, the first child of Charlotte and William Bloomberg. The family lived in Allston and later Brookline before settling in Medford in 1945, near William’s bookkeeping job at a Somerville dairy.
Medford was then a blue-collar town of predominantly Irish and Italian families. At the end of World War II, an undercurrent of anti-Semitism still kept Jewish families, like the Bloombergs, from living in certain neighborhoods, including the middle-class development they chose in West Medford, across from Oak Grove Cemetery. The Bloombergs’ Irish attorney had to purchase their new house — a modest stone and shingle Garrison Colonial at 6 Ronaele Road — and resell it to them to circumvent the realtors’ refusal to sell to Jews.
His mother, Charlotte, told biographer Joyce Purnick that she was the disciplinarian in the house while her husband doted on their son.
At Medford High, Bloomberg was a bright but lackluster student. He was “totally bored,” as he recalled in his 1997 memoir, “Bloomberg by Bloomberg," until his senior year, when he took the school’s only honors courses — in literature with Sharkey and in history. For the first time, he wrote, he was “interested in and challenged by” his schoolwork. He was an Eagle Scout, a member of the Slide Rule Club, and president of the school’s Debating Society, formed by a group of seniors to debate such pressing issues as capital punishment, immigration, and “recognizing Red China,” according to the school’s 1960 yearbook. He worked at a small electronics company in Cambridge on weekends, after school, and during the summer.
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In the class dictionary, in which students were assigned a defining characteristic, Bloomberg was labeled “argumentative.”
Outside of school, according to his memoir, Bloomberg read “Johnny Tremain" dozens of times, a novel about a teenage messenger and spy for the Yankee rebels in Boston in 1776, and often took the T to visit Revolutionary War sites in downtown Boston. He said he identified with the patriots “sticking it to old George III" and still tries to emulate their maverick spirit.
Although they traveled in different social circles, Richard Black, a retired Methodist minister living in Lancaster and president of Medford High’s class of 1960, remembers Bloomberg as friendly but assertive, prone to saying what he thought no matter the consequences.
“He had a little bit of an edge and sometimes rubbed people the wrong way,” said Black, who sat in front of Bloomberg in homeroom through middle and high school. Black is now volunteering for the Bloomberg campaign, making calls to prospective voters from the campaign’s Lowell field office.
“I think it would be wrong to paint him as an aloof billionaire who doesn’t know what it’s like to work for a paycheck," Black added. "He grew up with us, and we all did, and our families did.”
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Carmen Comite, who also graduated from Medford High in 1960, said Bloomberg "was one of the geeks like we were.” Comite, a former Gillette executive who retired to Florida, was president of the Slide Rule Club, wherein he and other members, including Bloomberg, would time one another as they solved calculations with their analog calculators.
The students at the school were mostly working class. Their parents were strivers — immigrants or children of immigrants who worked hard so their children could get ahead. By the middle of the 20th century, Medford’s population was booming. According to Black, Medford High’s class of 1960 had 690 students. But as Bloomberg wrote in his memoir, the school was focused on vocational training and few students matriculated to college.
The idea that one of their peers could one day compete to lead a major party’s presidential ticket was unfathomable, said Comite.
“I think almost all of us were blue-collar kids who didn’t know a whole heck of a lot about anything other than that our parents were kicking us out of the house and telling us to go get an education,” Comite said. “If anybody in this Slide Rule Club said they were gonna run for president of the United States, we probably all would have laughed.”
Remembering his roots
Even as Bloomberg amassed his fortune through his financial, media, and software empire, Bloomberg LP, his mother continued to live at their Ronaele Road home until her death in 2011 at the age of 102. (His father died decades earlier while Bloomberg was an undergraduate studying engineering at Johns Hopkins University in Baltimore.)
Bloomberg was very close with his mother and visited frequently. He donated $1.5 million to Temple Shalom in Medford, Charlotte’s beloved synagogue, where she served as copresident well into her 90s. When she died, Bloomberg requested donations be made to the Medford Public Library in her honor. Through the years, he also supported his hometown’s public schools, alumni orchestra, local hospital, and sports complex, according to The New York Times.
His largess extended beyond Medford to another touchstone from his childhood: Boston’s Museum of Science, where he used to spend Saturday mornings, dazzled by lectures, exhibits, and demonstrations. In 2016, he gave $50 million to the museum, the largest charitable gift in its history, to fund educational programs in science and engineering.
Today, his childhood home, unoccupied but well-maintained, remains in the Bloomberg family. It was last sold to his sister, Marjorie Tiven, a New Yorker who runs a nonprofit under Bloomberg Philanthropies, for $10 in November 2019, according to city records. In an interview with the Globe, Bloomberg said he still pays for the home’s phone line, so he can listen to his mother’s voice on the answering machine whenever he wants.
“If I want to hear her, I can just call the number,” Bloomberg said.
Yet Bloomberg said he remains no more personally invested in winning Massachusetts than any other state. Perhaps he is quietly bracing for disappointment. A Feb. 18 poll of the Massachusetts primary suggests Bloomberg may not earn a single delegate of the 91 the state’s Democratic voters will award.
The poll, conducted by veteran Democratic operative Lou DiNatale and former gubernatorial candidate Evan Falchuk, shows Vermont Senator Bernie Sanders in a statistical tie with Massachusetts Senator Elizabeth Warren, with support from 17 and 16 percent of likely voters, respectively. Bloomberg trails with 13 percent support. At least 15 percent is needed to capture a delegate.
And despite Bloomberg’s copious amounts of cash, he faces an uphill battle as his opponents capitalize on his prior policy failures and scandals. Just days before his campaign announcement in November, Bloomberg finally apologized for promoting stop-and-frisk during his time as New York’s mayor, a policy that research has shown did little to curb crime and was deemed unconstitutional by a federal judge. His recently resurfaced 2008 comments blaming the economic crash on the end of “redlining,” a discriminatory housing practice, further threaten to alienate him from voters of color. Bloomberg also has come under fire for his history of demeaning comments toward women at his company, several of whom are silenced by strict nondisclosure agreements.
But his supporters say they are willing to look past those controversies to elect the candidate they believe is the Democrats’ best shot at unseating Donald Trump.
“I have to forgive his transgressions — the ‘Me Too’ transgressions coming out now," said Schepps, his former classmate. "I think the most important issue in the election is to not reelect Trump, and I think Michael is our best bet.”
At the grand opening of the Bloomberg campaign’s Medford office on Sunday afternoon, almost 300 people arrived for a chance to meet a Bloomberg surrogate, actor Michael Douglas, and to pick up some campaign materials — buttons, bumper stickers, and yard signs. Philomena Zero Murphy, one of Bloomberg’s former Medford High classmates, was there, contemplating taking home a yard sign. She remembered Bloomberg as a smart and quiet kid who hung out at Brigham’s ice cream in Medford Square.
“I was up in the air [about which candidate to vote for], but I got a little feeling that I think he’s going to do well. I think he’s got a lot of good points," Murphy said. She’s leaning toward supporting him. “I’d like to see someone I sort of grew up with become successful."
Deanna Pan can be reached at deanna.pan@globe.com. Follow her @DDpan. James Pindell can be reached at james.pindell@globe.com. Follow him @jamespindell and on Instagram @jameswpindell.