Leonard Riggio, a brash, self-styled underdog who transformed the publishing industry by building Barnes & Noble into the country’s most powerful bookseller before his company was overtaken by the rise of Amazon.com, has died at age 83.

Riggio died Tuesday “following a valiant battle with Alzheimer’s disease,” according to a statement issued by his family. He had stepped down as chairman in 2019 after the chain was sold to the hedge fund Elliott Advisors.

“His leadership spanned decades, during which he not only grew the company but also nurtured a culture of innovation and a love for reading,” reads a statement from Barnes & Noble.

Riggio’s near-half century reign began in 1971 when he used a $1.2 million loan to purchase Barnes & Noble’s name and the flagship store on lower Fifth Avenue in Manhattan. He acquired hundreds of new stores over the next 20 years and, in the 1990s, launched what became a nationwide empire of “superstores” that combined a chain’s discount prices and massive capacity with the cozy appeal of couches, reading chairs and cafes.

“Our bookstores were designed to be welcoming as opposed to intimidating,” Riggio told The New York Times in 2016. “These weren’t elitist places. You could go in, get a cup of coffee, sit down and read a book for as long as you like, use the restroom. These were innovations that we had that no one thought was possible.”

He grew up working class in New York City, liked to say he preferred socializing with childhood pals over fellow business leaders and was informal enough among associates to be known as “Lenny.” But in his time no one in the book world was more feared. With the power to make any given book a best seller, or a flop, to alter the market on an idle whim, Riggio could terrify publishers simply by suggesting prices were too high or that he might sign up such top sellers as Stephen King and John Grisham and publish them himself. He even tried to buy the country’s biggest book wholesaler, Ingram, in 1999, but backed off after facing government resistance.

By the end of the 1990s, an estimated one of every eight books sold in the U.S. were purchased through the chain, where front table displays were so valuable that publishers paid thousands of dollars to have their books included. Thousands of independent sellers went out of business even as Riggio insisted that he was expanding the market by opening up in neighborhoods without an existing store. Instead, independent owners spoke of being overwhelmed by competition from both Barnes & Noble and Borders Book Group, the rival chains sometimes setting up stores in close proximity to each other and to the locally owned business.

Barnes & Noble became so identified as an overdog that one of the 1990s’ most popular romantic comedies, “You’ve Got Mail,” starred Tom Hanks as an executive for the “Fox Books” chain and Meg Ryan as the owner of an endangered independent store in Manhattan.

“We are going to seduce them with our square footage, and our discounts, and our deep arm chairs, and our cappuccino,” Hanks’ character confidently declares. “They’re going to hate us at the beginning, but we’ll get ’em in the end.”

For a time, it seemed industry conversation was an ongoing response to Barnes & Noble. Publishers were known to change the cover or title of a book simply because a Barnes & Noble official had objected. “Angela’s Ashes” author Frank McCourt found himself condemned by the American Booksellers Association, the trade organization for independents, after agreeing to appear in a Barnes & Noble commercial. On the floor of the industry’s annual national trade show, long hosted by the ABA, independent store employees would hiss at attendees wearing Barnes & Noble badges.

When novelist Russell Banks, addressing Barnes & Noble’s annual shareholder meeting in 1995, declared that he was both a stock holder and a happy B&N customer, some independent sellers stopped offering his books.

“You must know that I’ll never read, buy or sell another word you write,” Richard Howorth, owner of Square Books in Oxford, Mississippi, wrote to him. “These are the kindest things I can think of to say to you.”

Tensions led to legal action when the ABA — on the eve of the 1994 convention — announced it was suing Barnes & Noble and five leading publishers for unfair trade practices. Some of the publishers were so angered they boycotted the gathering the following year and only returned after the ABA sold the show to Reed Exhibitions. In 1998, the ABA sued Barnes & Noble and Borders for unfair business practices (both cases were settled out of court).

Riggio began the 2000s at the height of power, with more than 700 superstores and hundreds of others outlets. But internet commerce was growing quickly and Barnes & Noble, with its roots in physical retail, lacked the imagination and flexibility of the startup from Seattle that called itself “Earth’s Biggest Bookstore,” Amazon.com. The online giant launched in 1995 by Jeff Bezos gained business throughout the 2000s and by the early 2010s had displaced Barnes & Noble through such innovations as the Kindle e-book reader and the Amazon Prime subscription service.

Bezos would liken himself to David taking down Goliath, although the contrast between the leaders also had the feel of an Aesop’s fable: The muscular, mustachioed Riggio, a boxer’s son, upended by the quick and clever Bezos.

“We’re great booksellers; we know how to do that,” Riggio acknowledged to the Times in 2016. “We weren’t constituted to be a technology company.”

Barnes & Noble started its own online site in the late 1990s, but such initiatives as the Nook e-book reader and a self-publishing platform failed to stop Amazon. Not even the collapse of Borders after the 2008-2009 economic crisis mattered for Barnes & Noble, which after decades of expansion closed more than 100 stores between 2009 and 2019.

By the time of Riggio’s retirement, independent sellers regarded the chain not as a threat, but as an ally in the fight against Amazon to keep physical stores alive. At the 2018 booksellers convention, Riggio and ABA CEO Oren Teicher, once enemies in business and in court, praised each other during a joint appearance.

“My standing here, doing what I’m about to do (introduce Riggio) would have been impossible to imagine several years ago,” Teicher said at the time. “The simple fact is that our business is stronger and American readers benefit when there is a vibrant and healthy network of brick-and-mortar bookshops all across the country.”

During the 2010s, Barnes & Noble seemed unleadable and unwanted. The board announced in 2010 that the company was for sale, but no one offered to buy it. Four CEOs left in five years and Barnes & Noble’s stock dropped 60% between 2015 and 2018. New rumors of a sale lasted for months before Elliott Advisors, which had previously purchased the British chain Waterstones, bought Barnes & Noble for $638 million and hired Waterstones chief executive James Daunt to lead B&N.

“I don’t miss being a business person, I had enough of that. But I do miss the bookselling part, helping to find books to recommend to customers,” Riggio told Publishers Weekly in 2021.

Bookselling and family often overlapped for Riggio. His brother Steve Riggio served for years as vice chairman of Barnes & Noble and another brother, Thomas Riggio, helped run a trucking company that shipped the store’s books. After being interviewed in 1974 by the trade publication College Store Executive, Leonard Riggio met for coffee with the editor, Louise Altavilla, who seven years later became his second wife (Riggio had three children, two with his first wife, one with his second).

Leonard S. Riggio was the eldest son of a prize fighter (who twice defeated Rocky Graziano) turned cab driver and a dress maker. Even in childhood, he advanced quickly, skipping two grades and attending one of the city’s top high schools, Brooklyn Tech. He studied metallurgical engineering at New York University’s night school before focusing on commerce, and by day absorbed the bookselling world and the rising cultural rebellion of the 1960s.

Working as a floor manager at the campus book store, he learned enough to drop out of school and start a rival shop in 1965 — SBX (Student Book Exchange), where he allowed student activists to use the copying machine to print copies of anti-war leaflets. SBX was so successful he bought several other campus stores and was in position by 1971 to buy Barnes & Noble and its single Manhattan store. A few years later, he became the rare bookseller to run television commercials, with the catchphrase “Barnes & Noble! Of Course! Of Course!”

Riggio and the independent community may have seemed to hold opposing values, but they shared a love of reading and the arts and a liberal political outlook. He was a generous philanthropist and a prominent supporter of Democratic politicians. He was even friendly with the consumer activist and presidential candidate Ralph Nader, who featured Riggio, Ted Turner and Yoko Ono among others in his 2009 novel “Only the Super-Rich Can Save Us!”, in which Nader imagines a progressive revolution from above.

“Ever since he was a boy from Brooklyn, he’d had a visceral reaction to the way workings stiffs and the poor were treated on a day-to-day basis,” Nader wrote of Riggio, who did at times stand apart from his management peers. When some 200 business leaders were questioned by Fortune magazine in the 1990s about their political ideas, only Riggio supported the raising of worker pay.

“Money can become a burden, like something you carry on your shoulders,” he told New York magazine in 1999. “My nature is to be a ball-buster, but my role is to help people.”