The 50 Wealthiest Bostonians

There are more than 58,000 millionaires in the Boston area. Meet our town's richest fat cats.

Massachusetts has always had more than its fair share of millionaires. It’s been that way for two centuries, ever since Salem’s Elias Hasket Derby’s profits from the China trade made him America’s first. Today nearly one in 20 families here is worth at least $1 million. That’s more per capita than in Los Angeles, Chicago, even New York City. In Weston, the ratio is one in four. And they’re getting richer. Over the past two decades the wealthiest households in this state have seen their incomes rise five times faster than the poorest and twice as fast as those in the middle class.

Not everybody at the top has fared so well since we last produced this list. David Wetherell of CMGI, for example, saw his stake in the company plummet from $2.1 billion to $100 million in less than a year. Others took their green to greener pastures. Viacom’s Sumner Redstone, now worth $8.4 billion, moved to Beverly Hills. Casino baron Sheldon Adelson, who once drove his purple Rolls-Royce home to Newton, took his $15.6 billion to Las Vegas, where he owns the Venetian. Buyout king Thomas Lee ($1.2 billion) made like Johnny Damon and split for New York.

But most of our entrepreneurs endure—and profit. There clearly are still fortunes to be made in such necessities as real estate and healthcare. Unlike the virtual billionaires, titans of manufacturing continue to prosper. Money managers who help the rich get richer are doing pretty well themselves. More than ever, the people on this year’s list accumulated their fortunes by making products or deals bigger, faster, riskier, and smarter than their rivals—not, as used to be the case here, by inheriting their money.

Experts say another 30,000 households will hit the $1 million mark in Boston in the next four years. We’ll be keeping score. How we compiled the list.

1. Abigail P. Johnson

44, Milton; president, Fidelity Employer Services
$13.5 billion

The sixth-wealthiest woman in America, Johnson last year abruptly left the Fidelity funds’ board of trustees and was transferred from her job at the head of the underperforming mutual-funds division. But don’t worry: She’ll be okay. Johnson is reportedly the company’s single-biggest shareholder, and the fast-expanding employer services division she now oversees represents more than half its assets under management. And she is still widely expected to succeed her father, Edward “Ned” Johnson III, at the top of the world’s largest mutual fund company, which manages $1.2 trillion.

2. Edward C. Johnson III

75, Nahant; CEO and chair, Fidelity Investments
$6.5 billion

Some speculate that Johnson will finally go out to pasture within five years. But make no mistake: The old lion still roars. When the SEC said it would bar executives who chair mutual fund companies from having a financial interest in the funds they manage, Johnson fired off a scathing op-ed piece to the Wall Street Journal (he chairs all 377 Fidelity funds and his family owns nearly half the company). “Any darn mule can kick down a barn,” Johnson wrote to investors. And Fidelity, worth an estimated $40 billion, is the biggest barn around.

3. John E. Abele

69, Concord; director, Boston Scientific
$3.3 billion

After meeting at their kids’ soccer game, Abele and Peter Nicholas (No. 4) cofounded Boston Scientific in 1979 and together still own about a third of the medical equipment leader, which stands to become the state’s largest publicly held company with its $27 billion acquisition of Guidant. Abele and Nicholas have always taken risks. Their drug-coated stent, Taxus, introduced in 2004, sold faster than Viagra. And, despite paying out $750 million in an embarrassing trade-secrets settlement last year, their company still controls some 60 percent of the U.S. market in drug-coated stents. Most of the rest is controlled by archrival Johnson & Johnson—which lost the ruthless fight for Guidant.

4. Peter M. Nicholas

64, Boston; chair, Boston Scientific
$2.8 billion

The businessman to cofounder John Abele’s scientist, Nicholas knows exactly what money can buy. At his alma mater, Duke, for example, $20 million got him the Nicholas School of the Environment and Earth Sciences in 1995 (he’s gone on to donate another $100 million to the university). Boston Scientific is playing with even higher stakes: Its $27 billion acquisition of Guidant will make it the world’s leading cardiovascular device maker. And give Nicholas more money to spend.

5. Amos Barr Hostetter Jr.

69, Boston; chair, Pilot House Associates
$2.3 billion

Hostetter saw the potential of cable TV when everybody else was still struggling with rabbit ears. Foresight like that pays off: He sold Continental Cablevision, which he cofounded with Celtics CEO Wyc Grousbeck’s father, Irv, for $11.6 billion. Now he lives on Beacon Hill, near the Kerrys and one of the ex–Mrs. Stembergs, and is busy behind the scenes of several companies. He has used a large part of his fortune to endow the state’s biggest philanthropic organization, the $800 million Barr Foundation, while his wife heads the board of the Isabella Stewart Gardner Museum as it undertakes its first-ever expansion and a fundraising campaign whose target is reportedly some $60 million to $100 million.

6. (Tie) Herb Chambers

64, Boston and Old Lyme, CT; president, the Herb Chambers Companies
$1.8 billion

Chambers, who never went to college, was a Dorchester boy just out of the Navy when he talked his way into a job fixing copy machines in Cambridge. By the time he was 22, he had started his own copier distribution company, which he eventually sold for $80 million. Chambers’s rise to the top of the world of auto sales has been just as fast, and even more profitable. His chain of 30 dealerships, begun in 1985, now accounts for one out of every three luxury cars sold in eastern Massachusetts, reaping more than $1.4 billion a year in sales. Among his own 15 cars, Chambers has a $1.7 million McLaren F1, purportedly the fastest car in the world and one of the rarest (Jay Leno once begged for a test drive, then bought his own). His other assets include a $60 million, 188-foot yacht, the Excellence III; a $34 million Gulfstream G450 jet; a helicopter; a Connecticut marina; and a condo at the Mandarin Oriental, where preconstruction prices
started at $2 million.

John P. “Jack” Manning

57, Boston; CEO and president, Boston Capital
$1.8 billion

Manning’s company is the fifth-largest owner of apartments in America, with 147,000 of them in 48 states. His wealth and his role as a Democratic fundraiser also make him very well connected; if his friend John Kerry had been elected president, Manning might now be our ambassador to Ireland. Bill Clinton occasionally stops by for lunch at Manning’s office or to golf with him and Kerry on the Vineyard. Manning also serves on the boards of Beth Israel Deaconess and the JFK Library Foundation. His toughest decision: which of his two Bentleys to drive to the meetings.

8. (Tie) James S. Davis

62, Newton; CEO and chair, New Balance
$1.6 billion

Davis hustled to put together the $10,000 down payment for New Balance, which he bought on Marathon Monday in 1972. Good deal. Now New Balance and Reebok are neck and neck for the title of America’s second-largest athletic shoe brand (Nike is first).

Arthur S. Demoulas

47, Concord; director, Demoulas Super Markets
$1.6 billion

The longest (15 years), costliest (at least $13 million) civil litigation in state history whittled away at the Demoulas fortune as two sides of the family struggled for control of their $2 billion-a-year Market Basket chain. But the Supreme Court has now put an ostensible end to the saga by declining to hear another installment of Demoulas versus Demoulas. That seemingly means Arthur S.’s family will hang on to the controlling interest in the Demoulas Super Markets company a judge took away from cousin Arthur T.’s side. What it doesn’t mean is that they’re going to kiss and make up: They’ll be furious to be even mentioned together here.

Stephen R. Karp

65, Weston; CEO and chair, New England Development
$1.6 billion

A few years after making his way through BU by working summers in construction, Karp convinced his then employer, a real estate development firm, to go in with him on a shopping center in Danvers. The Liberty Tree Mall became the first in a string of 20 malls he would develop, before selling most of them for $1.75 billion. Karp still owns the CambridgeSide Galleria and much of downtown Nantucket, where he bought about $75 million worth of property last year alone. Now he’s setting his sights on Newburyport, where he spent $38 million on commercial space last year. His Westin Boston Waterfront hotel, codeveloped with Joe O’Donnell (No. 24), is scheduled to open in July.

11. (Tie) Richard J. Egan

70, Hopkinton and Boca Raton, FL; cofounder, EMC
$1.3 billion

When the blunt-spoken, Dorchester-born ex-Marine teamed up with fellow Northeastern grad Roger Marino to get in on the ground floor of the data storage business, their office was his living room, his wife was their first employee, and they sold office furniture on the side to make ends meet. Now that company, EMC, is the state’s second largest based on market capitalization (nudged out of first in January by the Boston Scientific–Guidant deal). And even though Egan resigned as ambassador to Ireland after only 18 months, he is still one of George W.’s top guys. A 2003 fundraiser at his Hopkinton home, attended by Dick Cheney, Mitt Romney, and 700 others, raised $1.4 million for the GOP.

Thomas J. Flatley

74, Milton; CEO and chair, the Flatley Company
$1.3 billion

Flatley arrived from Ireland in 1950 with $32 and made himself into one of the nation’s wealthiest real estate moguls. Now, at 74, he’s slowly taking himself out of the game. He sold his chain of hotels for $470 million, and thousands of apartments for $500 million—the biggest deal ever in this state. But Flatley’s not slowing down altogether: He’s working on a multimillion-dollar deal in Quincy’s Crown Colony Office Park.

13. (Tie) Amar G. Bose

76, Wayland; founder and chair, Bose
$1.2 billion

If Massachusetts had a state genius the way it has a state bird (the chickadee), Bose would be it. For the past 25 years, the MIT Ph.D. has been developing an ultrasmooth car suspension system (code name: Project Sound) that promises to pimp your ride the way his high-end speakers pimp your family room. Dr. Bose—as his employees unfailingly call him—puts all the profits from his privately held company’s estimated $1.8 billion in annual sales back into research. If he led a public company, Bose has joked, that would have gotten him fired. Instead, he’s gotten richer. Go figure.

John W. Childs

64, Chestnut Hill; president, J. W. Childs Associates
$1.2 billion

The notoriously media-shy Childs remains a cipher, but the brands his private equity firm has bought into are well known: Brookstone, NutraSweet, Meow Mix. He spearheaded one of the most successful deals in buyout history while still learning his trade at Thomas H. Lee Partners, buying Snapple for $135 million and flipping it two years later for $1.7 billion. Some predict Childs will do it again with Sunny Delight, which he bought for an estimated $300 million two years ago. Nicknamed the Republican ATM, he has given lavishly to GOP causes.

15. (Tie) Ernest Boch Jr.

48, Norwood; CEO and president, Boch Enterprises
$1.1 billion

Higher profile than archrival Herb Chambers (No. 6), Boch has become a fixture on the charity circuit and in commercials for his six car dealerships (four of which his late father made famous). He obviously got the salesmanship gene: Ernie Jr. sold 900 cars last Presidents’ Day weekend alone. He inherited his father’s sense of humor, too, pledging $500,000 to Caritas Norwood Hospital and asking that the morgue be named for him. Last year he sold his four Cape Cod radio stations for $21.3 million. That will buy a lot of gas for his $15 million Citation Sovereign private jet and the $100,000 stretch Subaru that takes him home at night to the $7 million compound he’s building for himself in Norwood.

Paul B. Fireman

62, Brookline; former CEO and chair, Reebok International
$1.1 billion

When Brockton native Fireman mortgaged his house to buy distribution rights for an unknown brand of athletic shoes in 1979, his wife had to sell encyclopedias door-to-door to help pay the bills. The risk paid off: The couple stands to make $800 million from the $3.8 billion sale of Reebok to Adidas. An avid golfer, Fireman already has a second career teed up: His New Jersey golf course, said to be the most expensive ever built, is scheduled to open July 4.

Robert K. Kraft

64, Brookline; owner, CEO, and chair, New England Patriots
$1.1 billion

After graduating from Harvard Business School in 1965, Kraft went to work at his father-in-law’s paper company, Rand-Whitney. Less than three years later, he took over half the company in a leveraged buyout (no doubt making for some uncomfortable family Thanksgivings), then built it and his own International Forest Products into one of the world’s largest paper conglomerates. Of course, he assumed a higher profile in 1994 with his then record $172 million purchase of the Pats (his former Brookline neighbor Jeffrey Lurie broke the record later the same year by buying the Philadelphia Eagles for $185 million). Twelve years and three Super Bowls later, the Patriots franchise alone is worth an estimated $1 billion (we’ve deducted the value of that $15,000 Super Bowl ring now sitting in Vladimir Putin’s sock drawer). Now Kraft, who also owns the Revolution, is said to be developing Patriots Place, a “man mall” anchored by a Bass Pro Shops, on his 500 acres around Gillette Stadium. And Kraft’s mom wanted him to be a rabbi . . .

18. James J. Pallotta

47, Wellesley; vice chair, Tudor Investment
$1 billion

Head of the $9 billion Raptor Fund, Pallotta is consistently ranked among the 20 top hedge-fund managers in the nation (and is the 11th-highest-paid, earning a reported $195 million in 2004). He’s known for his philanthropy—he gives millions each year through his charitable trust—and personal investments including stakes in Via Matta and the Celtics (for which he ponied up a reported $20 million). Plus, he’s cool enough to hang with U2, as he did at Radius last December and in a private box at the then FleetCenter. When Pallotta’s not hobnobbing in town with celebrities or working at his office in Rowes Wharf, he’s bound to be comfortable in the $19 million, 33,528-square-foot compound he’s building on 27 acres in Weston.

19. Edward G. Watkins II

70, Concord; philanthropist
$950 million

The first Edward G. Watkins founded fire- and security-equipment manufacturer Simplex Time Recorder in 1902, shortly after inventing the first practical time clock. Under Edward II’s reign, the company made a fortune in institutional fire alarms. After selling Simplex for $1.2 billion, Watkins no longer has to worry about money. But time is still on his mind: He reportedly owns an impeccably landscaped, 9,200-square-foot section of Crystal Lake Cemetery in Gardner.

20. Kenan E. Sahin

64, Boston; founder and CEO, TIAX
$904 million

Sahin owned 100 percent of his billing software company, which he sold to Lucent Technologies for a cool $1.48 billion (he gave $100 million to his alma mater, MIT, tied for the largest gift ever received by the school). Now he is the sole owner of Tiax, a technology research and development firm that operates 50 labs in Cambridge and California. The company’s researchers are tinkering with everything from better-tasting pediatric antibiotics to smart fabrics that can withstand the rigors of outer space. Closer to home, Tiax owns the PlaceLab condominium near MIT, where it studies how technology can improve home life.

21. John W. Henry

56, Brookline and Boca Raton, FL; principal owner, New England Sports Ventures; founder and chair, John W. Henry & Company
$840 million

After leading the group that bought the Red Sox in 2002 for $700 million—more than twice the highest previous price for a sports team—Henry has become our most famous snowbird. Sure, his $3.1 billion investment firm’s funds reportedly lost $400 million in December alone, capping off its worst year ever. But Henry can spend the off-season in comfort on his $6.5 million Florida estate. During baseball season he docks his $34 million, 164-foot yacht, the Iroquois, at Rowes Wharf. And when he asks his guests to remove their shoes to protect the teak deck, he gives them red socks to wear.

22. Teresa Heinz Kerry

67, Boston; philanthropist
$750 million

John Kerry may be America’s wealthiest senator, with an estimated personal fortune of at least $164 million, but even that’s not enough to get him onto this list. As Kerry himself has joked, he married up. His wife, Teresa—after whose name inevitably come the words “heir to her late husband’s ketchup fortune”—has so much money that the wealthy senator had to sign a prenup before they walked down the aisle on Nantucket. (It’s no big deal, Mrs. Kerry has remarked: “Everybody has a prenup.”) And since Kerry couldn’t use any of Teresa’s considerable assets in his presidential bid, he was reduced to taking out a $6.4 million mortgage on their 170-year-old Beacon Hill townhouse (five bedrooms, eight baths, 169 light fixtures).

23. William I. Koch

63, Osterville and Palm Beach, FL; founder, the Oxbow Group
$735 million

Last year’s MFA show “Things I Love: The Many Collections of William I. Koch” was both cheered and jeered (“monumentally egomaniacal,” one critic called it). It featured nearly 200 masterpieces from Koch’s art collection, including works by Monet, Cézanne, and Picasso, and two of his yachts—the one he skippered to victory in the 1992 America’s Cup, and the one that came in second, which he bought after the race. (Sadly, the exhibit didn’t include any specimens from his 35,000-bottle wine collection.) Koch is perhaps equally famous for his collection of ex-wives—he agreed to pay his second one $16 million in their acrimonious 2001 divorce. He’s now married to Bridget Rooney, who previously had a son with Kevin Costner. Koch’s fortune began with his father, an oil industry tycoon, but he sued two of his brothers for more money after they paid him and another brother $1 billion for their shares of the company, and his mother over her distribution of a trust fund. Koch later founded his own energy firm, the Oxbow Group.

24. Joseph J. O’Donnell

61, Belmont; founder and chair, Boston Culinary Group; owner, Allied Advertising
$725 million

The son of an Everett cop, Joe O’Donnell started in business renting out tuxes for the Malden Catholic prom. A speaker at a Boston event would later quip, “I want to thank my friend Joe O’Donnell for renting a tie for the night.” Okay, it wasn’t a particularly funny joke, but the speaker was O’Donnell pal President George W. Bush. O’Donnell has a lot of friends in high places (so many that we’ve named him Boston’s most powerful person), and while we’re sure it’s largely on account of his unassuming personality, the money doesn’t hurt (he raised at least $200,000 for Bush in the last election). He built concessions giant Boston Culinary Group into a company whose 11,000 employees provide food services to stadiums and other venues, and owns Allied Advertising, the third-largest print advertiser in the country. He also has stakes in movie theaters, ski resorts, and restaurants including John Harvard’s Brew House. And he’s a partner, with longtime friend Steve Karp (No. 8), in the $200 million Westin set to open in July at the convention center.

25. John F. “Jack” Welch

70, Boston; retired CEO, GE; principal, Jack Welch LLC
$720 million

Welch made $10,500 in his first year as a young chemical engineer at GE. In his last year as CEO, he made $16 million. Though investors balked at his estimated $50 million retirement package, he did increase GE’s worth by $400 billion during his two decades as CEO, making it for a time the most valuable corporation in the world. Now Welch lives with his third wife, Suzy Welch, née Wetlaufer, in a leased 20,000-square-foot townhouse overlooking Boston Common. He owns four other homes, including one in Nantucket, where he has paid for college scholarships for caddies from the island’s Sankaty Head Golf Club (Welch always gets the best caddies). He’s unapologetic about falling for Suzy—whose ring finger carries 10.8 carats of diamonds—while still married to his second wife, though said wife is rumored to have diminished his fortune by more than $100 million in the divorce (the settlement remains sealed).

26. (Tie) Stephen R. Weiner

64, Boston and Palm Beach, FL; founder, S. R. Weiner & Associates
$700 million

Like Boston real estate’s other Steve—Steve Karp (No. 8)—Weiner has profited nicely from New Englanders’ irresistible need to shop in temperature-controlled comfort: He helms 70 shopping centers, including his new crown jewel, the Derby Street Shoppes in Hingham. Weiner and longtime mentor Julian Cohen (No. 41) are partners with man-about-town Robin Brown in the ultraluxurious $278 million Mandarin Oriental hotel and residences, where many of the other überwealthy people on this list will live. Weiner is forward-thinking in another way, too: He and his wife just gave $6 million to Beth Israel Deaconess to fund stem-cell research.

Margot C. Connell

64, Swampscott; chair, Connell Limited Partnership
$700 million

Before industrialist William F. Connell died in 2001, he told Forbes: “People are rich when you have what you need in the world. A nice family, a good education, to participate in the community. That is rich.” Now his widow, Margot, chairs the more-than-$1-billion family business. She also carries on her husband’s philanthropy. In 2003, for example, she gave $5 million to Caritas St. Elizabeth’s Medical Center.

28. John A. Kaneb and family

71, Manchester-by-the-Sea; chair and CEO, H. P. Hood; president, the Catamount Companies
$600 million

John Kaneb knows you can make a fortune selling life’s necessities—in his case, milk and oil. A specialist in buying stakes in struggling or underperforming companies, cutting their costs, and improving their efficiency, Kaneb bought a controlling interest in Gulf Oil, then more than tripled its sales to $4.6 billion before quietly selling the stake last year. The Kanebs acquired Hood in 1995 and increased its annual sales from $600 million to around $2.3 billion, due in large part to their willingness to spend money on new products. He’s also a part owner of the Red Sox, over whose home games often hovers the Hood blimp.

29. David G. Mugar

66, Boston and Cotuit; CEO, Mugar Enterprises
$550 million

This heir to the Star Market fortune is the epitome of old-money Boston. He gives generously to such charities as the Boston Pops Fourth of July Esplanade concerts, which he famously bankrolled for 27 years, and he seems to have a stake in everything: residential developments including the under-construction Mandarin Oriental (where he has bought a luxury condo to add to his collection of expensive homes in Cotuit and St. John’s), shopping centers, and his Brownfields Recovery Corporation, which cleans up contaminated industrial sites and builds new office parks.

30. Edward H. Linde

64, Weston; cofounder, CEO, and president, Boston Properties
$546 million

Trained at MIT as an engineer, Linde was smart enough to go into commercial real estate instead. He founded Boston Properties 36 years ago with publishing magnate Mort Zuckerman and focused on iconic buildings in the country’s three priciest markets: New York (the $654 million Times Square Tower), San Francisco (the $1.2 billion Embarcadero Center), and Boston (the $519 million Prudential Center). Linde is also chairman of the board of trustees at the BSO. And Wall Street is playing his tune: His company’s stock price has nearly doubled in the last two years.

31. Jeffrey N. Vinik

46, Weston; Founder, Vinik Asset Management
$515 million

Like Peter Lynch (No. 40) before him, Vinik made his name running Fidelity’s Magellan Fund. He started his own company in 1996 and made investors a reported 93.8 percent return in his first 11 months (and about 50 percent a year for each of the three years after that). Then he gave them back their $4.2 billion to focus on his own portfolio. Vinik, who also owns a piece of the Red Sox, just sold his $2 million Weston colonial and moved into a $12.5 million Weston mansion. He can afford it.

32. Richard A. Smith

81, Chestnut Hill; cochair, the Richard and Susan Smith Family Foundation
$500 million

Smith’s father gave him a head start on his bank account by founding a small chain of theaters in the 1920s that would become General Cinema. Smith used to play tennis with Bob Kraft (No. 15) and is the uncle of Philadelphia Eagles owner Jeffrey Lurie. But it wasn’t his connections that made Smith his fortune. Now in his eighties, he built—and has been selling off—an empire that included a soda bottler, a major publishing company, and department stores. In 1989, Smith sold his independent soda-bottling company to PepsiCo for $1.88 billion, then the highest price ever paid for a bottler. He used some of the proceeds to buy Harcourt Brace Jovanovich for $1.5 billion. Then Harcourt sold in 2001 for nearly four times that. Finally, he and his family grossed more than $600 million in the $5.1 billion sale of Neiman Marcus. That adds up to a very comfortable retirement.

33. John F. Fish

46, Milton; CEO and president, Suffolk Construction
$425 million

When he took over the embryonic Suffolk from his father at 22, Fish didn’t even make as much as a good plumber. Meanwhile, the older and larger family business, Peabody, went to his brother Ted. Twenty-four years later, Suffolk is the biggest construction company in New England, with an estimated $1.1 billion in annual revenue, competing regularly with the smaller Peabody for jobs (and usually winning). Fish’s fingerprints are all over the state: He put up the $10.7 million Seiji Ozawa Hall at Tanglewood, managed the $147 million John Adams Courthouse renovation, and is building the $278 million Mandarin Oriental and the $150 million Westin Boston Waterfront hotel. Now he’s plowing some of his fortune back into causes including the Boston Pops, whose big Presidents at Pops event he chaired last year.

34. Gururaj “Desh” Deshpande

55, Andover; founder and chair, Sycamore Networks
$412 million

Deshpande has had a long fall from the heady days when he started Cascade Communications with $1,000 and sold it for $3.7 billion, then founded Sycamore Networks, which boasted the fourth-largest IPO of all time. Those successes pushed his net worth to a peak of $13 billion, making him the wealthiest Indian on earth. Sycamore’s share price has since plummeted from a high of about $200 to less than $5, and Deshpande and his CEO, Dan Smith (No. 38), are stuck with 32 percent of the stock. Of course, that’s one-third of a company still valued at almost $1 billion. Meanwhile, he continues to invest in other startups.

35. Stephen G. Pagliuca

51, Weston; managing director, Bain Capital
$410 million

Pagliuca, who chairs three local children’s charities, spends his rare free time rooting for his kids’ sports teams—he goes to as many as 10 games in a weekend—or shooting hoops on the regulation court at his $6.4 million Weston home. When he’s not doing that, he’s rooting for the Celtics, in which he and the team’s three other managing partners reportedly invested $140 million toward the $360 million total purchase price (he was brought in on the deal by Wyc Grousbeck, who he knew because their kids went to the same school). A leveraged-buyout artist, Pagliuca came into money like that by helping engineer more than 30 acquisitions at Bain Capital, Governor Mitt Romney’s old firm. Its $3.5 billion pitch last year to buy the entire NHL is the rare Bain idea that didn’t work out. Too bad for hockey.

36. Swanee G. Hunt

55, Cambridge; director, Women and Public Policy Program, Harvard University
$407 million

Hunt may have been born with the proverbial silver spoon in her mouth—her late father, oil baron H. L. Hunt, was once reportedly the richest man in the world—but she’s spent most of her life trying to give it away. An advocate for women and a former ambassador to Austria, she gives half her income to charity through her two foundations. That adds up to about $60 million so far.

37. Ronald M. Druker

62, Boston; president, the Druker Company
$400 million

Druker is exceptional, his competitors say, because he carries little debt on the 50-odd hotels and apartment buildings he owns or manages. Druker, whose father built the Colonnade, has added to the family portfolio with the Heritage on the Garden and the Colonnade Residences, once home to Kevin Millar and Trot Nixon. And he sold all 103 luxury condos in his critically acclaimed Atelier 505 (at prices of up to $3.3 million per) five months before it opened. Druker also chairs the Rose Kennedy Greenway’s proposed New Center for Arts and Culture, which he persuaded architect Daniel Libeskind to design.

38. Daniel E. Smith

56, Wellesley; CEO and president, Sycamore Networks
$392 million

Think you’ve lost money in the market? The value of the Smith family’s stake in Sycamore has fallen from a peak of $2.7 billion to about $210 million. Of course, that still makes for a soft landing. The Harvard M.B.A. sold some of his shares in happier times, letting him stash away a few tens of millions for a rainy day. And he and cofounder Desh Deshpande (No. 34), who jointly led Cascade Communications to a $3.7 billion payoff, are seeing black ink on the books again. Sycamore’s revenue last quarter was up 92 percent over the same period the year before.

39. Patrizio Vinciarelli

59, Boston; chair, CEO, and president, Vicor
$370 million

Vinciarelli founded Vicor, which makes power supply devices, after an antiquated power converter set his stereo on fire. He had no business experience, his laboratory was his basement, and his startup investors were his relatives and friends. Lucky for them. Today, though Vicor’s share price has yo-yoed since its 1991 IPO—Vinciarelli once lost $408 million in a week—the company’s stock is rebounding. So is Vinciarelli’s net worth. He’s planning to sell up to a million shares in the coming months, which stands to add at least $18 million to his bank account.

40. Peter S. Lynch

62, Boston; vice chair, Fidelity Management & Research
$352 million

If you’d invested $1,000 in Fidelity’s Magellan Fund on Lynch’s first day as manager, you’d have had $28,000 on his last day, 13 years later. He didn’t do so badly for himself, either. Now he monitors his $74 million charitable foundation and lends his magic to the portfolio of his alma mater, BC, which grew 18.8 percent in 2004—outperforming Harvard’s. He’s also dabbling in real estate. Last year the Lynchs bought a $6.1 million condo overlooking the Public Garden, and—together with their daughter and son-in-law—a $5.1 million house on Beacon Hill. They also picked up two nearby parking spaces for $340,000, presumably as a housewarming gift.

41. Julian Cohen

81, Boston and Palm Beach, FL; partner, CWB Boylston
$350 million

Called Julie by his friends, Cohen hired protégé Steve Weiner (No. 26) just after Weiner graduated from BU to help him run his real estate development business. They’ve worked together ever since on projects including the new Mandarin Oriental. Cohen has given millions toward the $31 million Cohen Pavilion at Palm Beach’s ritzy Kravis Center for the Performing Arts, $2 million toward the Cohen Galleria at the MFA, and $13 million to the BSO, including $1 million toward the Cohen Wing at Symphony Hall.

42. Henri A. Termeer

60, Boston and Marblehead; CEO, chair, and president, Genzyme
$342 million

In 1981, Genzyme, which develops treatments for rare diseases, employed 14 people in an office in Chinatown. Eighteen months later it hired the Dutch-born Termeer. Now the biotech firm has a payroll of more than 8,000 in 70 offices and plants worldwide, making it the third-largest company of its kind. Not really a surprise, then, that Termeer was the area’s highest-paid CEO in 2004, raking in a total compensation package worth at least $37.9 million.

43. Landon T. Clay

79, Brookline; Peterborough, NH; and Providence, RI; chair, East Hill Management
$316 million

Clay’s expensive hobbies have kept him busy since he stepped down as chair of the financial services company Eaton Vance in 1997. An armchair mathematician—even though he majored in English at Harvard—he underwrote the Clay Mathematics Institute in Cambridge, which is offering $1 million for each answer to seven of the most significant unsolved math problems (a Russian mathematician is said to be close to solving one). He’s also helped finance observatories for Harvard (to which he has given at least $14 million over the years) and the Dexter and Southfield schools in Brookline.

44. Douglas A. Berthiaume

56, Andover; CEO, chair, and president, Waters Corporation
$314 million

Berthiaume, who has run lab-equipment maker Waters since it was spun off from Millipore in 1994, collected just $650,000 in salary in 2004. But on a single day that year, he exercised more than 1.8 million stock options at $4.07 a share, according to SEC filings. Then he turned around and sold them all, grossing roughly $16 million. Don’t begrudge Berthiaume his wealth; his investors don’t. His company’s stock price has grown more than 1,000 percent since its 1995 IPO. He’s also a big giver to Mitt Romney.

45. (Tie) Steven B. Belkin

58, Weston; chair, Trans National Group
$300 million

Belkin invented affinity marketing—selling branded credit cards and travel packages to such groups as professional associations and alumni clubs. But money can’t buy everything. What Belkin really wants is to own a major-league sports team. After twice trying to buy the Celtics, he finally became principal owner of the Atlanta Hawks and Atlanta Thrashers, only to be bought out by his partners in an ugly dustup. In January he asked a court to either award him the value of his 30 percent stake in the franchises—which he estimates to be worth $500 million—or force his former partners to sell them back to him. Just in case, he’s still in the market for another team.

Jerome Lyle Rappaport Sr.

78, Lincoln and Stuart, FL; cofounder, New Boston Fund; Philanthropist
$300 million

The legacy of Rappaport’s Charles River Park (“If you lived here, you’d be home now”) is still up for debate. But it’s not his problem anymore: He and his partners sold off the Emerson Place complex for $72 million, the Longfellow Place towers for $240 million, and Charles River Plaza for an estimated $80 million. Most of his time is now spent helping direct his $10 million charitable foundation from his homes in Lincoln, Nantucket, Florida, and Vermont.

47. Timothy P. Horne and family

67, Andover and Naples, Fl; director, Watts Water Technologies
$283 million

North Andover–based Watts Water was founded in 1874 to build steam regulators for New England textile mills. It still builds similar equipment in 50 plants worldwide, including some as far afield as China and Tunisia. And though Horne retired in 2002, his family still controls more than 40 percent of the company’s stock.

48. Raymond S. Stata

71, Dover; cofounder and chair, Analog Devices
$269 million

In 1996 Stata stepped down as CEO of semiconductor maker Analog, a company he cofounded. The next year he and his wife gave $25 million to MIT, his alma mater, which named its new Frank Gehry–designed center for computer science for them. Then in 1999 the Statas gave $10 million to the BSO, endowing the music directorship—now held by James Levine—in perpetuity. If those gifts trimmed the couple’s fortune, it was only temporarily. In 2000, Stata refilled his coffers with $68 million (before taxes) from further Analog stock sales.

49. Barbara Lee

60, Cambridge; philanthropist
$213 million

Her 1996 divorce from buyout king Tom Lee made Barbara Lee a very wealthy woman. (Her net worth got another boost when she sold their Brookline home for $18.5 million, then a city record.) She’s since started a foundation to support women in politics, hosted a $500,000 fundraiser in October for Hillary Clinton and the three other women U.S. senators up for reelection, and given the first $5 million toward the new $62 million ICA, whose capital campaign she cochairs.

50. Thomas G. Stemberg

57, Boston; venture partner, Highland Capital Partners
$202 million

Venture behemoth Bain Capital floated him $3 million when he was starting Staples. Now Stemberg, who says he was forced out of the company he founded, is a venture capitalist himself. Along the way, he’s invested some of his own money in KaBloom florists, Zoots dry cleaners, and Olly Shoes, a chain of children’s shoe stores he helped finance in partnership with a woman who later became his mistress—thanks to which a chunk of Stemberg’s estimated $202 million net worth shown here may already belong to his ex-wife.

How We Did This: We combed through 18,000 pages of documents to calculate these estimates, including annual reports, proxy statements and other SEC filings, court papers, and real estate records. Taxes were subtracted from stock sales when that information was available. To determine the wealth of people associated with privately held companies, we spoke to colleagues, competitors, fundraisers, public relations representatives, attorneys, and gossips, and estimated the value of some private companies by comparing them with similar public ones.