The Envy Issue

Of all the Seven Deadly Sins, Boston’s always had the weirdest relationship with envy. For centuries, good fortune in this city was a private and occasionally gloomy thing, to be brooded over inside Commonwealth Avenue mansions or Louisburg Square townhouses, behind heavy curtains kept drawn for the sake of decency. Correspondingly, envy was a thing perhaps felt by many, but voiced by few. There was an unspoken pact: I won’t shove it in your face, and you won’t hate me for it. If there was public envy, it was couched in moral terms and expressed from above, not below. We don’t hate you for your success; we hate you for thinking your success means anything. We feign concern for you when, by our accounting, you’ve gotten too big for your britches. We tut-tut. We recite ancient aphorisms. Sic transit gloria, and so forth.

Not anymore. At some point, as Boston went cosmopolitan, wealth become giddy. For those who possess it, good fortune, even as the financial markets go haywire, is no longer something to hide. Flashy cars, once only the province of unctuous Eurotrash BU students, are now everywhere. Countless glass-fronted (!) ultraluxury condo complexes are being erected all over town. Designer pets and the pampering thereof is all the rage. Battalions of staggeringly expensive baby carriages roll through the South End, past parking spaces that go for six figures.

Predictably, this explosion of public gluttony (some may say “prosperity”) has triggered a vigorous round of public envy, fueled by the intense insecurity Bostonians have always attempted to conceal, or at least sublimate by going to a Bruins game and screaming, “Yankees suck!” for 45 minutes. With so much of the stuff going around, it’s gotten hard to separate the envier from the envied. They feed off each other. You accumulate status symbols as a response to the discomfort of being made to envy someone else’s. You look to lessen your envy pangs by inspiring them in someone else. The cycle rolls on.

As long as that’s the governing dynamic, we say: If you’re going to play the status game, or even just watch it, it helps to understand the new rules that govern it, and at whom to direct your most potent jealous longings. Over the course of these special pages, we spell out both. If nothing else, the next time you find yourself asking, “Why not me?” you’ll know the answer—and how you might do something about it. —Joe Keohane

Jealous Much? No matter how sprawling your summer home, how shiny your medals, how gracefully curvilinear your jawline, there are always bigger, shinier, curvier assets to covet. Namely, the types of nonpareils that have elevated the following Bostonians to our list of the most envied people in town. To them, we must say thanks: But for their maddening example, we might have remained obliviously trapped in prisons of complacent self-worth, and never clamored for more.

The Half-Baked Ham
Dane Cook, “comedian”
Cook is … not funny. This has been widely documented: e.g., Boston rock station WBCN officially named him “The Unfunniest Comic,”and a North Carolina musician put out an ambient-electronica CD called Dane Cook Isn’t Funny. Yet Cook, who grew up in Arlington, has managed to record two platinum-selling DVDs, host Saturday Night Live, sell out Madison Square Garden, and get paid to roll around half-naked with big-screen hotties (including Kate Hudson in last month’s My Best Friend’s Girl). None of which has made him any more funny.
Envied by talented, underexposed comics

The RSVP VIP
Lisa Pierpont, socialite
This shout-out actually goes to Pierpont’s thankless stunt double, who’s clearly making it possible for the Brahmin scenester to appear to be everywhere at once. Her work as editor of the website Boldfacers guarantees entry to myriad parties and, thus, photo ops galore—which always catch her looking fabulous because, well, she’s freakin’ gorgeous. (Not to mention that designers like Louis Vuitton clamor to dress her for free.) If impeccable taste, a matchless social calendar, and gobs of money weren’t enough, she’s also an Emmy-winning broadcast journalist and a hands-on mother whom local rags describe as a “bon vivant.” She’s also genuinely lovely, even to us mere mortals. Dammit.
Envied by her stunt double, fashion “don’ts”

The Radio Head
Michael Felger, sports commentator
From Herald football scribe to ESPN Radio talker to Comcast SportsNet and WBZ pundit, Felger has deftly spanned the local sports-media spectrum with nary a suspiciously perfect hair out of place. Over the years, whether in print or on air, he’s taken athletes, coaches, and owners to task with admirable fearlessness. Now holding forth regularly on WEEI, Felger is as unavoidable in Boston as “Sweet Caroline”; unlike the song, however, we never get sick of him. Bonus points: He’s married to the seriously hot and impossibly likable Sara Underwood.
Envied by Dan Shaughnessy

The Geek Goddess
Cynthia Breazeal, robot maker
why she’s envied Visit any company along the Route 128 corridor and you’ll meet disillusioned schlubs who did not grow up fantasizing about writing code for database software. Breazeal is still living the dream. As director of the Personal Robots Group at the MIT Media Lab, she gets paid to create cutting-edge robots that act like people, look like Muppets, and receive loads of government grant money. Thanks to her specialization in “highly expressive robotic faces,” she’s also Hollywood’s go-to android guru: Stephen Spielberg flew her in when he directed A.I.
Envied by C++ programmers, supply-chain management software gurus, people who need people

The Other Celine
Celine Oringer (Mrs. Ken)
She can snag the best seat in the house at Clio or Toro or any one of her celebrity-chef husband’s other packed eateries—or, better yet, come home after a long day to seared Nantucket Bay scallops and slow-roasted Kobe rib-eyes, cooked and served by the legend himself. Young, glamorous, and successful in her own right, the French-American beauty stays above the fray of the notoriously catty restaurant industry. We really want to hate her, but we got nothin’. Well…she is part French.
Envied by Olivia English

The Kraft Junketeers
Power-player pilgrims Steve DiFillippo, Ken Oringer, George Regan, Richard Seymour, Barry Shrage, and Benjamin Watson
Shortly after the end of the NFL season each year, New England Patriots owner Robert Kraft rounds up a group of local VIPs for a trip to Israel. Ostensibly intended to support the billionaire’s charity, the swish jaunt has also turned into the ultimate schmooze fest. During this year’s trip, Pats players Richard Seymour and Benjamin Watson kicked back at the home of Israeli Prime Minister Ehud Olmert (a Kraft pal), and PR guru George Regan struck a deal with restaurateur Steve DiFillippo, owner of Davio’s and Avila, to rep his restaurants. DiFillippo’s newest spot? A third Davio’s at Patriot Place, of course. Touchdown!
Envied by The “Positively Cleveland!” junketeers, execs who make deals on the links

The Good Shepherd
Matt Damon, actor
The consummate nice guy, he’s not too cool to poke fun at himself (see: the infamous Sarah Silverman video) or come home for Sox games without mugging for the paps (see: Ben Affleck). It’s how we all swear we’d act if the windfall would ever finally come, sweet Christ! But deep inside, we know the truth is grimmer. Admired for funneling the millions he’s made as Hollywood’s most bankable male lead into a number of charitable pursu… Our apologies, Matt. We’re out of time.
Envied by Ben Affleck, Jimmy Kimmel

The Agent Provocateur
Beth Dickerson, real estate pro
why she’s envied This downtown Realtor is the one to call when your Aunt Eunice finally kicks it and you’re itching to unload her double-wide brownstone double-quick. A former bartender who married well, Dickerson hit it big with her own boutique real estate firm, then hit it bigger when she merged it with Sotheby’s. These days, she doesn’t even pick up the phone for anything less than two mil. Dickerson also finds time to remain a fab fixture on the social and charity scenes, and loves seeing her name in print almost as much as she loves closing high-dollar deals.
Envied by Beth Dickerson, Bugaboo Creek hostesses

The Sole Man
Sam Hassan, co-owner of the Tannery
why he’s envied Shops selling $300 limited-edition sneakers practically outnumber Dunkies franchises in Boston today, but it was Hassan who pioneered the concept locally, earning himself a tidy fortune in the process (and a reputation for heckling walk-in customers who exhibit questionable footwear taste). Now that he’s passed much of the daily business operations to his nephew, finding new ways to spend bales of cash is hobby number one. Among the old ways: purchasing chunks of prime Boston and Cambridge real estate, including the penthouse atop the Four Seasons.
Envied by Obsequious shoe salesmen, Thom McAn

The T-Shirt Tycoon
Johnny “Cupcakes” Earle, fashion entrepreneur
At 26, this skater punk turned mogul is getting rich selling T-shirts stamped with cupcake designs, the new releases of which inexplicably draw throngs of eager customers to his Johnny Cupcakes stores in Hull and on Newbury Street. The brand reached Hub-side saturation a couple of years ago, but its outpost on L.A.’s hipster haven Melrose Avenue quickly picked up the slack, and now Colette—Paris’s hipper, French-er answer to Louis Boston—is adding Earle’s “invention” to its shelves. Though he’s always said he launched the business as a joke, Earle now earnestly declares on his website: “Every type of person collects, understands, and appreciates my brand.” Oh, shut your pie hole, Johnny Cupcakes.
Envied by those guys hawking “Wicked Pissah” T-shirts at Fenway

The Star Whisperer
Nick Paleologos, executive director of the Massachusetts Film Office
A former state representative, Paleologos went on to produce a string of successful movies (including the critically acclaimed Quiz Show, Ghosts of Mississippi, and Hurlyburly) and launch the Stuart Street Playhouse. Today he spends the bulk of his time palling around with Hollywood heavies like Martin Scorsese and Robert Redford as the head of the agency tasked with luring moviemakers to our state. What that job entails aside from attending cocktail parties and delivering overly generous tax credits is anyone’s guess, but it’s nice work if you can get it.
Envied by Secretary of Elder Affairs Michael Festa, Christy Scott Cashman

The Sticky-Bun Queen
Joanne Chang, chef and restaurateur
why she’s envied The Harvard-educated baker spends days rolling out batches of killer sticky buns at Flour and nights serving up fatty potstickers at Myers + Chang, yet somehow manages to stay fabulously fit. As if brains, beauty, and buns weren’t enough, Chang also stomped a mudhole in Bobby Flay’s smug New York ass in a Food Network bake-off.
Envied by Ina Garten, carb-starved dieters

The Anti-Flack
Marlo Fogelman, publicist
Glad-handing journalists, soothing ruffled clients, typing up cheery blurbs about deserted, overpriced lounges…most humans simply don’t have the fake-smile wattage required of the typical publicist. Refreshingly, neither does Fogelman. Her testy demeanor and frumpy fashion sense—let alone her willingness to undermine a client in the name of honesty—haven’t stopped her from bagging major accounts and getting all up in the grill of fellow publicists, who scratch their heads at her success. A licensed lawyer, Fogelman sits on the boards of enough charities, foundations, and charitable foundations to make Angelina Jolie look like a layabout.
Envied by whoever keeps pitching us “Litewear for the Family.” (There’s your mention. Please stop now.)

Tommy Terrific
Tom Brady, Patriots quarterback
True, he shredded his knee in the first game this season. But the break from his gridiron chores just leaves him more time to perfect cold fusion and find life on Mars, in between cashing endorsement checks and snuggle sessions with Gisele.
Envied by Drew Bledsoe, Jesus

The Home-Maker
Ofer Nemirovsky, venture capitalist
Flouting the worst foreclosure crisis in recent U.S. history, this venture capitalist is splicing two Back Bay buildings into a 24,000-square-foot, five-floor mansion. The imperial abode, commanding the corner of Exeter Street and Commonwealth Avenue, includes bathrooms and dressing rooms for each of his three children, an elevator, a roof deck, and the requisite “ball-playing court.” According to his employee profile at HarbourVest Partners, Nemirovsky speaks Hebrew, but apparently he’s not familiar with the concept of diaynu.
Envied by The Joneses

The Purple Pieman
The Phantom Gourmet, mysterious food reviewer
why he’s envied Pigging out and complaining are two of our favorite pastimes, and every restaurant critic is in the enviable position of doing both on the company dime. Channel 38’s Phantom Gourmet does that lot one better by dining in disguise, which keeps spurned chefs from hunting him down with cleavers. Also: that natty purple cape, which helps hide extra pounds—the food he favors tends toward the cheese-slathered.
Envied by Billy Costa, suburban gluttons, corporeal gourmets

The Absolutely Fabulous
Joshua Janson, man of leisure
Janson gained a measure of renown with a recent New York Times Magazine article featuring his marriage to Benjamin McGuire, a fast-tracked associate at Greenberg Traurig. But the Times didn’t come close to capturing Janson’s posh lifestyle. If he’s not stopping to smell the roses (which he cultivates on the roof of his chichi South End penthouse), then he’s celebrating his existence with orgiastic parties on islands or schooners, or the best tables at any given restaurant. During a weekend-long fete in Nantucket last summer, the staff at the island’s Ralph Lauren outpost offered to close the store to the public so he and his friends could shop undisturbed. And back in the city, the morning after an “impromptu” Dom Pérignon–soaked bash at the Taj, he got a call from the bar manager—who, far from complaining, just wanted to compliment the youth and vivacity of Janson’s unruly crowd.
Envied by Jonathan Soroff, the Boston Gay Men’s Chorus tenor section

The Heirs Unapparent
Elizabeth Johnson and Ned Johnson IV, Fidelity heirs
Abigail Johnson—eldest daughter of and likely successor to Ned III, and head of Fidelity’s personal and workplace investing division
—is the richest person in the state. Not too shabby, Abby, but your younger siblings take this spot. Free of the constant job stress and press scrutiny faced by big sis, but with more than enough spending power, Elizabeth enjoys kicking back at her home in ritzy Louisburg Square and jumping show horses at her stable in Florida. And then there’s Ned Quattro, a senior veep at Fidelity’s Pembroke real estate arm, who majored in recreation and leisure studies at Northeastern—a savvy choice of diplomas if ever there was one.
Envied by Arthur and Michelle Wahlberg

The Guilt-Tripper
Samantha Power, journalist
She won’t quit harshing our mellow with gut-wrenching stories of human-rights atrocities, but the top judges of journalism dote on Power anyway, having awarded her a Pulitzer for her buzzkill of a first book, A Problem from Hell: America and the Age of Genocide. And while she lost a gig as an adviser to Barack Obama when she referred to Hillary Clinton as a “monster,” she gained a reputation as a badass, not to mention a husband—intellectual hottie Cass Sunstein, a Harvard Law prof whom she met while both were working for the campaign. We’re sure he was attracted to her mind, and all. But for a certain type of guy (which apparently includes this mag’s online editor), Power also qualifies as bona fide babe.
Envied by anyone whose love nest doesn’t double as a brain trust, nuns

The B-Movie A-Lister
Christy Scott Cashman, president of Saint Aire Productions
This actress/producer/writer/trophy wife once suffered for her art. But after working really, really hard and—oh, yeah—marrying construction magnate Jay Cashman, she and Saint Aire Productions finally claimed a piece of the limelight. Since moving with her husband into their killer Back Bay mansion, she has produced such groundbreaking feature films as Homie Spumoni (2006), and, just for kicks, now cohosts NECN’s Open Book Club with Debbie DiMasi, another aspiring entertainer relying solely on her own native talent.
Envied by C-movie B-listers, Project Greenlight rejects

The Lucky Dog
Catie Copley, hotel pet
As official canine ambassador of the Fairmont Copley Plaza, the nation’s most famous Labrador retriever has a rock star’s life, which is to say that she’s often passed out in a hotel lobby when not making personal appearances, posing for pictures, or going for scheduled walks with guests who book her affection months in advance. Best of all, Catie Copley never has to beg for food or love. We don’t know a lot of people who have that luxury, let alone dogs.
Envied by Lonely people, hungry dogs

The Lucky Dawg
Jerry Remy, NESN broadcaster
Turned a career as a slap-hitting infielder for the Sox and Angels into every sports junkie’s dream gig: getting paid to sit on his can and watch baseball. Prone to forgetting which two teams are playing, giggling fits, and one-way conversations with his Wally the Green Monster doll, the “Rem Dawg” has become an icon to Sox fans everywhere. Despite his goofiness and porn-star mustache, he’s living proof that there are second acts. Although in his case, it’s no act.
Envied by Bill Buckner, Bill Simmons, bleacher bums