A familiar name, an interrupted record

Stephen Taylor did not want to sell the newspaper his family had run for more than a century.

At the time of the 1993 sale to The New York Times Co., he was 42 years old and in charge of The Boston Globe’s technology, presses, and buildings. Taylor figured he would be part of a new generation to lead New England’s largest daily paper, with his cousin Benjamin next in line to run the Globe. And he was in the thick of his biggest project yet - launching the paper’s website, Boston.com, at a time when most people in the industry failed to see the Internet’s potential.

Both men lobbied top executives to keep the paper in the family, but to no avail.

Now, Taylor, 58, is trying to buy back the Globe, for a sliver of the $1.1 billion the Times Co. paid for it. He is the great-great grandson of the paper’s first publisher, a fifth-generation member of a clan with newspaper ink in its veins. Taylor’s last name got him his first job at the Globe, and he’s trying to leverage the family name again. His pitch to investors: He’ll preserve the Globe’s journalism and craft a new business model to support it.

It has been a tough sell. Some wealthy Bostonians spurned Taylor’s early overtures, wary of investing in what they consider a dying industry, according to people involved in the bid. With final offers due tomorrow, Taylor is still scurrying to raise money. He has to convince investors he has what it takes to make it in a radically shifting newspaper landscape, despite having been out of the business for nearly a decade.

Since 2000 - when he was the last Taylor to leave the Globe - he has not worked full time. He has dabbled in high-tech start-ups, making small investments in young online publishing companies and advising them. He’s handled the family’s trust finances and, for the past three spring semesters, he has taught a three-hour-a-week course on media financing to MBA students at Yale University, his alma mater. And he has pursued his passion for sailing, spending summer days on his 45-foot sloop in the waters of Buzzards Bay.

Richard Daniels, a former Globe president, said he believes Taylor’s group is passionate about the Globe and its effect on the community. But, he added, “Operating a newspaper in the year 2000 or earlier, and in the year 2009, are vastly different activities.’’

Daniels, who is now chief executive of GateHouse Media Inc. in New England, owner of The Patriot Ledger of Quincy and other community newspapers, said it’s much tougher to make money in the business today than it was when the Taylors ran the Globe. Competition for readers has intensified, with the proliferation of online news sites and the rise of Google. And the days when hundreds of millions of dollars in printed classified ads supported the operation are long gone, he said, supplanted by online services such as Craigslist.

Taylor declined to discuss specifics of his Globe bid. But in an interview, he said, “I’ve been studying this very closely for the last three years and I’m eager to practice what I’ve been teaching - together with a strong team dedicated to innovation, quality journalism, and the city of Boston.’’

He started as a management trainee in 1980 and did a stint as a reporter, covering police and fires. Over the years, his responsibilities spanned from overseeing the janitorial staff and the repair of the helicopter landing pad atop the Globe headquarters on Morrissey Boulevard to managing a $50 million color-printing upgrade and building new plants. He is also credited with overseeing the paper’s conversion from manual paste-up of its pages to a more efficient computerized system.

When he left nine years ago, he was executive vice president, in charge of information technology, operations, and administration, and about half the company’s 2,500 employees. He was also president of Boston Globe Electronic Publishing, running Boston.com in its first five years of operation. It was the job he considered most important, people who know him say.

Taylor’s team includes Globe veterans, among them former president and financial chief William Huff, 59, and former technology chief Robert Murphy, 54. But Taylor would also hire younger talent if he were to become publisher of the Globe, he has told associates, especially in sales, marketing, and digital publishing. “He doesn’t mind if he’s not the smartest guy in the room,’’ said one former colleague.

For all his enthusiasm and affection for the Globe, Taylor has little of his own money to invest. Since the paper’s sale, much of the $200 million or so that flowed to Taylor and more than 100 of his relatives has remained tied up in family trusts. Through a complicated set of rules, money becomes available only after older family members die. By one family estimate, Taylor won’t see meaningful cash until he’s 70.

In preliminary bids, Taylor’s group and a rival bidder, Platinum Equity of Beverly Hills, Calif., each offered about $35 million for the Globe and the Worcester Telegram & Gazette - also owned by the Times Co. - plus the assumption of $59 million in pension liabilities. It’s possible the Times Co. could expect a higher price now, with the Globe’s finances improving and the economy brightening. It’s also conceivable the Times Co. won’t sell the paper.

Taylor gained some momentum in his fund-raising last month, when his second cousin, former Globe publisher Benjamin B. Taylor, joined the team as an investor. Another cousin, Alexander “Sandy’’ Hawes, also is investing, according to people involved in the bidding. It’s unclear how much Taylor’s relatives are putting into the deal. Hawes was traveling and could not be reached for comment.

Benjamin Taylor, 62, was the last family member to run the Globe. He was publisher from 1997 to 1999, when he was fired by the Times Co. and replaced with a Times executive, Richard Gilman. In an interview before he joined the investor group (and before he, Stephen Taylor, and others signed papers promising not to discuss the deal), Benjamin Taylor said, “Emotionally, it would be a very positive outcome to see the Taylors involved again.’’

But the pursuit of the Globe is more than emotional, he said. “It’s a question of who has a good management team to make the right decisions and get the business model right. And who has the financial wherewithal to create the space and time for it to succeed.’’

Sailing, not journalism, was Stephen Taylor’s first love. The US boycott of the 1980 Olympic Games ended his bid to compete in the two-person boat race, an event in which he had won three world championships. After that, Taylor accepted the invitation of then-publisher William O. Taylor, his second cousin, once removed - and someone he had only met a couple of times - to work at the Globe.

Stephen Taylor grew up in New Haven on the Yale campus, where his father was provost and a professor. He went to Phillips Academy in Andover for prep school and earned a bachelor’s degree in psychology at Yale. His father, Charles H. Taylor IV, who later became a psychoanalyst, never worked at the Globe but was a member of the board.

Taylor met his wife, reporter M.E. Malone, at the Globe, and they raised their two sons in Milton. In 1991, the couple took a seven-month leave to sail to Europe in their boat, the Meridian, returning by way of the Caribbean. It was an adventure they had long planned for, Malone wrote in a magazine story, detailing harrowing storms and stopovers on tropical islands.

Soon after their return, Taylor would face his greatest challenge at the Globe. It was 1993 and the Internet was starting to pick off advertising from the once-dominant, almost monopolistic, newspaper industry. Help-wanted advertisements were moving online, along with ads for homes and cars.

A longtime Globe editor, Lincoln Millstein, was already concerned about the Internet. “I worried about its power, its disruptive nature,’’ Millstein said in a recent interview. “You felt intuitively when you went online that this was going to cause problems.’’

Millstein and Taylor would lead the Globe to start publishing the newspaper on the Web - one of the first papers to do so - and establish Boston.com as a brand. But they first had to sell in-house skeptics on the new technology’s merits.

While Millstein led the charge on the news side, he credits Taylor with getting senior executives on board. “Steve is brilliant in his grasp of the enormous complexities of a multimedia company, his grasp of everything from how the printing presses work to distribution, to circulation, to pricing, to how we operated the Web,’’ Millstein said. “Of all the Globe executives at the time, I think he had the most well-rounded grasp of what was becoming a very, very complicated operation.’’

With the help of a young Stanford University business school graduate, Dave Margulius, Taylor and Millstein made countless presentations to Globe and Times Co. executives. There were lunches at the Algonquin Club in the Back Bay and, later, shuttle flights to Manhattan.

At the time of the Globe acquisition, they persuaded the Times Co. to make good on the Globe’s plan to put $3 million into Boston.com. Taylor pushed the idea of the site being broader than BostonGlobe.com, and when the time came to name it, Margulius said he woke up in the middle of the night with the answer - Boston.com.

But the name was taken. Au Bon Pain, the local restaurant chain, had reserved Boston.com to keep it from a competitor, Boston Chicken. Taylor called Au Bon Pain’s chief executive, Louis Kane, and told him he had a request. Taylor followed up with a visit to Kane’s South Boston office. No cash changed hands, but in return for the Boston.com Web address, the Globe would publish four ads in the paper for charities of Kane’s choice and help his company develop a website.

Taylor “was just a class act in how he thought about treating people, in how aggressive he was,’’ Margulius said. “And maybe because he was part of the family, he could cut through the clutter and get things done.’’

Taylor still loves technology, according to friends and colleagues. He’s a gadget guy who carries an iPhone and brags about the navigation system in his Acura sports utility vehicle.

His most expensive project was a multimillion-dollar Westwood plant the company bought in 1991 and refitted to automate the insertion of coupons and special publications into newspapers. For decades, the process, slow and expensive, was done by hand. The new inserting process worked, but the robots created to automate the moving of paper-loaded pallets never worked properly, according to company executives. A decade later, the Times Co. shut the operation down, sold the property, and moved the inserting equipment to Boston.

One of his biggest regrets, people who know Taylor say, was failing to persuade other Globe executives in the early 1990s to invest in the job website that would become Monster.com.

By 2000, Monster.com was generating $500 million in annual revenue, and the Globe watched its virtual lock on the help-wanted market vanish. “I’m sorry to tell you that’s an absolutely true story,’’ Taylor told a Globe reporter in April.

In recent years, Taylor has made a handful of early-stage venture deals, investing seed capital in start-up companies through his Densefog Group, a small investment entity. One is PaperG, a company started by a group of Yale and Harvard students in 2007 to work on selling local advertising for online publications; the company works with Boston.com and has seven-figure annual revenue. Another, Apture Inc., is a San Mateo, Calif., company that’s raised $4.1 million for multimedia publishing and to find ways to keep readers on websites longer. Both companies are too young to judge their success as investments.

By comparison, Taylor’s attempt to recapture the Globe is much riskier. His cousin Benjamin Taylor, the former Globe publisher, has acknowledged the enormity of the undertaking. “If it were easy to figure out how to solve this problem,’’ he said, “a lot of newspapers wouldn’t be in the situation they’re in.’’

Stephen Taylor said he believes newspapers can make money and deliver top quality journalism. “Measured by pure audience interest,’’ he said, “news and information have never been more relevant.’’

Beth Healy can be reached at bhealy@globe.com.