Looking for the Last of the Power Lunchers

While old Boston power-lunches at Davio’s (left), New Boston grabs a quick bite at Google’s gourmet café (right). / Photographs by Jared Kuzia (Davio’s), Toan Trinh (Google)

What is a power lunch?

There is no firm definition. It doesn’t really mean anything so much as it evokes a set of images: white tablecloths, bloody steaks. Men—old, rich, and almost always Caucasian—holding court at corner tables. Done deals. Slapped backs. Booze, ideally. And if the Power Lunch (the words almost beg to be capitalized) is synonymous with these things, then these things are synonymous with Davio’s.

For the first couple decades of its existence, Davio’s Northern Italian Steakhouse lived on Newbury Street. This was a good place to be in the 1980s and 1990s, when the city’s cultural center of gravity hovered nearby. The J. Geils Band, the Cars, and the Aerosmith guys popped in a lot. Matt Siegel—that’s Matty in the Morning to you—signed his first contract there, right after Kiss 108 bossman Richie Balsbaugh handed him the pen. Out-of-towner devotees included Joan Jett and Stevie Ray Vaughan. In 2002, Davio’s packed up and moved to a massive, bright, high-ceilinged location on Arlington Street. A celebrity quotient has remained—the Cleveland Cavaliers recently chowed there in the midst of a playoff-edition flaying of the Celtics. But the move downtown also brought in a new class of devout patrons: Boston’s homegrown politicos and corporate chieftains. Quickly, Davio’s cemented its status as a premier power-lunching destination.

At any given lunch hour at Davio’s, you’re likely to spot shopping-center mogul Stephen Karp, auto tycoon Herb Chambers, or hedge-fund master of the universe Seth Klarman. John Kerry, when he was secretary of state, was known to usher delegations of foreign diplomats into one of the restaurant’s discreet private dining rooms. Robert Kraft, meanwhile, beelines for the ever-desirable Table 60, which is visible from Arlington Street and offers a panoramic view of the dining room. Recently, WGBH’s Emily Rooney invited Holland & Knight law partner Brian Leary out to lunch. Naturally, they settled on Davio’s. Rooney describes the scene. The city’s kahunas circled the room, pumping hands here and there. “Jack Connors came over to our table,” Rooney says. “‘I’d like to get a piece of this action,” he said with a grin before ambling off. For his part, Connors, the former Hill Holliday chairman, says he feels “very comfortable at Davio’s.”

Davio’s is a safe space for the city’s captains of industry largely thanks to the expert stewardship of longtime owner Steve DiFillippo. Even at 56, he has the puppyish looks and middle-part hairdo of a ’70s teen heartthrob. And while he projects gee-whiz exuberance, behind the scenes, he’s tending to the brittle egos of his billionaire patrons. “Steve Karp used be partners with Robert Kraft on the stadium deal,” he says over lunch one day in June, pointing over to Table 110, where the septuagenarian developer is currently lunching. (Karp and Kraft purchased the old Foxboro Stadium in 1988, before Kraft bought him out a few years later, creating a rift.) “They’ve never said anything to me about it. But I’m not going to sit them right next to each other.” DiFillippo is known to shuttle among his four Massachusetts locations to shower arriving VIPs with his patented when-you’re-here-you’re-royalty hospitality.

Still, take a gander around the dining room, and “New Boston” is not a phrase that leaps to mind. It’s clear that the city’s fast-paced, innovation-based economy doesn’t exactly jibe with the clubby luncheon. When I called around town to ask people where they power-lunched, I was met on the other end of the line with what I imagine were raised eyebrows or blank stares. Red Sox CEO Sam Kennedy gushed about Chipotle and Sweetgreen as if they were chic new brasseries. Developer Ed Kane recommended the food-truck scene in Dewey Square. Venture capitalist Jeff Bussgang, of Flybridge Capital Partners, laid out his daily routine in an email that verged on self-parody: “630 crossfit. 800 breakfast in Boston. Or 600am run/bike/lift and then 730 breakfast in Newton. Lunch at my desk or on the go if I’m not in a board meeting. Buffalo meat and Rx bar or a piece of salmon.” Right. So no power lunch.

Or maybe “power lunch” just doesn’t mean what it used to. In the several restaurants I visited while reporting this story, virtually nobody (but me) was drinking. The summer day I visited Davio’s, 80 lunchtime patrons ordered a grand total of 12 alcoholic beverages—including the three I drained in the name of immersive journalism. What’s more, everyone’s in a rush to make it back to the office as quickly as possible—provided they’ve left the office at all. Lunching one afternoon at the Bristol, in the Four Seasons Hotel, I noticed that half of the restaurant’s most desirable window tables were completely empty by 1:30 p.m.

Is the testosterone-fueled Boston power lunch—for better or for worse—a thing of the past? Or has our Mad Men institution merely gotten a Silicon Valley makeover: healthier, brisker, and a little less fun? (Three-Soylent lunches, anyone?) Either way, I can’t help but think we might be leaving something worthwhile behind.

Ahead of the curve: Steve DiFillippo in front of his to-go lunch counter, which brings in $1 million of revenue a year. / Photograph by Jared Kuzia

Once upon a time, when Brahmins roamed the earth and rich people didn’t dare set foot in a public restaurant, the city’s power-dining scene was confined to private social clubs such as the Algonquin and the Somerset. The object was to steer clear of hoi polloi, not yet to see and be seen. Gradually, by the 1970s, when wealth and political power had migrated away from the city’s landed gentry, a handful of now-extinct restaurants—from the venerable Locke-Ober to the clubby Jimmy’s Harborside—moved the city’s backroom bossmen out into the open. Suddenly, the object was very much to see and be seen.

Back then, the lords of lunch tended to have a lot of time or a lot of money on their hands—and a vested interest in networking. In one corner: the politicos. Mayor Kevin White used to yo-yo along the perimeter of Boston Common and the Public Garden, from breakfast at the Ritz-Carlton, where the Taj now sits, to lunch at Locke-Ober, then back to the Ritz in the evening for a glass of chardonnay. (But never the Parker House, which he found overpopulated with political hacks.) When PR maven George Regan worked as a spokesman for White, he used to take Boston Globe reporters to expense-account meals so staggeringly often, the paper’s managing editor told Regan he assumed Regan was obese. Heady times, the ’70s. One ex-adviser to John and Bobby Kennedy—we’ll keep his name out of it, God rest his departed soul—was known to hold court every afternoon at the old Statler Lounge, in the Park Plaza. He’d drink three martinis and two Schlitzes with his meal, eventually paying the ultimate price for it.

In the other corner: local TV executives. Pre-cable, the big three local channels printed money like the U.S. mint. Which meant there wasn’t much work to do. Which meant there were a lot of midday meals to be had. “First of all, you always had a drink,” says Jim Coppersmith, Channel 5’s legendary former general manager. “And sometimes you had more than a drink. Sometimes you wonder how you got back to the station.” Which was located in Needham. The 84-year-old Coppersmith, who may have been sipping something delicious as we spoke, told me there were two good reasons to power-lunch. One: to wine and dine local advertisers. Two: “Establish yourself as a power player, as someone who mattered.” It was impossible to put a price on a postprandial digestif with the top execs at Blue Cross Blue Shield or Bank of America. “Lunch was very ritualistic, and a much more ceremonial thing than it is now,” Coppersmith says. “Now it’s eat it and beat it.”

When did that all change? A few of the city’s grand poobahs swear they haven’t liquid-lunched in decades. “I’m 75 years old,” Connors says. “If I go back to my youth in New York and then in Boston in the advertising business, lunch also included a couple glasses of John Dewar’s scotch and water. But I haven’t done that in probably 40 years.” Lobbyist Thomas O’Neill, son of bon vivant Tip, says he used to shuttle his father from Logan Airport straight to Jimmy’s Harborside upon the House speaker’s return from Washington. But he insists he himself hasn’t had a lunchtime drink in almost 50 years. So maybe those guys are saints. In general, though, it probably wasn’t until the 1980s and 1990s that the old-school power lunch started to fade.

One major factor was decentralization. First the suburbs got hot. Then Charlestown and the South End—among other neighborhoods—began to gentrify, further expanding the city’s power corridors. Restaurants branched out, too, reflecting the bourgeois bohemian tastes of the city’s yuppie class: In 1982, the stylish Seasons restaurant, which launched the careers of Lydia Shire and Jasper White, brought Boston into the culinary conversation. Five years later, Hammersley’s kicked off the city’s farm-to-table revolution. Then, in the mid-to-late 1990s, came the rise of the celebrity chefs: Todd English, Barbara Lynch, Jody Adams, and Ming Tsai. Gastronomy further evolved beyond glorified surf and turf, while fine dining no longer had to feel stuffy. “When I was [young], if you wanted a good meal, you had to go to a hotel,” Connors says. “Now, there are 50 wonderful places to have lunch.” Long story short, Boston’s dining scene got seriously crowded, diluting the influence of the city’s white-tablecloth powerhouses.

Then there were the trends that had nothing to do with Boston at all. Dieting and health fads took off, diminishing the volume of lunchtime sirloin and grain alcohol being swallowed. Steve DiFillippo thinks the success of anti-drunk-driving advocacy helped kill off midday boozing. Mintz Levin law partner Steve Weiner wonders if trendily noisy dining rooms wound up cutting lunches short. (What’s the point, when you can’t hear the guy across the table?) Then there was the state’s surprisingly strict 2009 ethics reform overhaul, which strongly discouraged lobbyist-legislator schmoozing.

Most salient of all, though, was a shift in the way business got done in Boston. Mike Sheehan, former CEO of Hill Holliday and the Boston Globe, traces our austere era back to the recession of the late 1980s. Before the economy tanked, Hill Holliday’s creative department essentially worked out of a Back Bay bar called Jason’s. After the crash, a number of Boston banks collapsed, the economy contracted, and the business climate became more competitive. Jason’s was abandoned. “It was a pretty fast transition to drinking at lunch not being good,” Sheehan says.

And from there, it was a pretty fast transition to…leaving the office for any reason not being good. A few years after the Jason’s era ended, Sheehan was working on the firm’s Fidelity account when he noticed the brokerage was hosting a lot of meals in a private-office dining room. Recession-related or not, the trend caught on with other firms. As Sheehan says, “You sit down with [State Street CEO] Jay Hooley, you get your menu, you order, it’s private, lots of laughs, he goes back to his office, and you go back to your office.”

Laughs or not, the changing corporate culture at Boston’s white-shoe firms only presaged the tech-ification of the city’s corporate environment, where “work” and “life” have been squished together—and “balance” isn’t always in the vocabulary. “Now you get brownie points for not getting a lunch break,” says Abe & Louie’s GM Nick Heilmann. “At places like Google and Amazon, you’re sort of out of favor if you disappear.” Which is why earlier this year, Legal Sea Foods impresario Roger Berkowitz carved out a standalone takeout restaurant at—where else?—his Kendall Square location. It’s called Legal Fish Bowl and all it serves are bowls. “Takeout has become more of a factor with millennials,” he says, “because they’re more apt to eat at their desks.” Certainly, the sad desk-salad tendency is a factor, but when it comes to the city’s new economy, it’s less that our beloved startups and tech monopolies are discouraging employees from enjoying lunch, and more that they’re dictating the terms of their meals.

Take Google’s Kendall Square campus. Lunch—prepared at two handsome on-site restaurants by veterans of Ten Tables and UpStairs on the Square, is offered gratis every day. The company sees its food program as part of a “holistic approach toward health and wellness” that encourages “casual collisions” between employees and contributes to the “overall mission of enabling Googlers to be their best.” I’m sure it’s pleasant enough to collide with your colleagues over venison burgers, but from the outside, it can look manipulative. “The naive me wants to think companies are providing food as a service to people so they don’t have to go hunting for lunch,” says Hill Holliday chairman and CEO Karen Kaplan. “But really, the cynical me says, ‘It’s a casino.’ Free meals are a way to keep you from leaving the building.”

The city’s work-hard-play-later corporate culture signals something else, too. Women, foreigners, and high-skilled employees increasingly dominate the city’s workforce—a sign of the meritocratic times. Long gone is the genteel complacency that allowed the good-old-boy bankers and TV execs to linger over lunches. It’s a shift that’s changed the very definition of power dining, from a drawn-out ritual in which powerful people bask in the glow of their influence to a brisk, unsexy calorie-delivery mechanism at which powerful people are merely present.

Case in point: As the power lunch fades, the power breakfast has increased its cachet. Far better, after all, to get one’s networking out of the way between the hours of 7 and 9 a.m. to facilitate a full, grueling day of uninterrupted labor. Hence the rise of Henrietta’s Table, in the Charles Hotel, as a go-to meeting spot for leading VCs and Harvard grandees. Meanwhile, as midday socializing goes extinct, real estate executive Kevin Phelan’s 40-year-running Breakfast Group continues to thrive. Why? Nobody’s there to have a good time! Every few weeks, at 8 o’clock sharp, several dozen invite-only VIPs pile into a conference room at Phelan’s Financial District office building and listen to a slightly more important VIP give a brief speech. After 20 minutes, hands are raised and questions are asked. Within an hour, everyone’s out.

This gets to another facet of the contemporary power-dining experience. The restaurant isn’t so much a place to escape the office as somewhere to take the office. When I ask Catalyst chef William Kovel if his Kendall Square restaurant has been overrun by laptops, I expect a resigned sigh. Instead, he seems pretty content to turn the place into a WeWork. “It’s part of the culture now; everything is so connected,” he says. “We offer free WiFi and plugs at the bar. We don’t have a cell-phone policy here.” Need to pace the dining room while yelling into your Bluetooth? Chef would be delighted!

So the Google economy, and a bunch of other culprits, pretty much killed the power lunch. What does that mean for the city? On the one hand, it’s kind of hard to mourn a ritual that systematically excludes everyone without the ability to sit around perpetuating their own privilege over Cobb salads. The demise of the power lunch might be the ultimate first-world problem. On the other hand, there’s a case to be made that something gets lost when you spend your lunch hour in a taco-truck line or hunched over your desktop scrolling through Twitter.

There are countless studies on this topic—maybe you’ve digested their findings while eating lunch at your desk—condensed into screaming Internet headlines. According to NPR, “We’re Not Taking Enough Lunch Breaks.” The Washington Post concurs that “You May Look More Productive Skipping Lunch, or Eating at Your Desk. But You Aren’t.” The HuffPost reinforces the point that “Eating at Your Desk Is Making You More Stressed and Less Creative.” (On the other hand, someone at Slate insists she’d “Rather Eat at My Desk.”)

A nonscientific survey of Boston’s power elite reinforces the same general idea. Kevin O’Leary, the Boston-based venture capitalist and Shark Tank judge, believes in the special power of the power lunch. When O’Leary wants to close a deal he goes to the same restaurant, the Taj, where he always sits at the same corner table. Then he orders a bottle of wine—one of his own, from the O’Leary Fine Wines collection the Taj keeps for him. If his guest doesn’t partake, he considers it an insult. The whole process is absurd and self-indulgent, but he swears it’s a huge part of his success. O’Leary claims he’s done $5 billion worth of deals there. Setting aside the juju of his particular table—also Number 60—it’s hard to argue with O’Leary on this point: “The whole thing about this that people miss is, when somebody commits an hour and a half of time to be with you, that’s a huge investment to get to that stage. The level of interest is high enough that they would commit 10 to 20 percent of their day to you,” he says. “An email is nothing. It can be deleted in two seconds and never read.”

The vestigial 20th-century power lunch catered to a handful of men who had the city to themselves. Few are eager to revive it. And yet, something about the ritual “breaks down barriers,” says George Regan, recalling the meetings he brokered between Kevin White and journalists or developers. Not to overstate the case here, but the nation seems gripped by a Hydra of political polarization, tech-induced distractibility, and restless, postmodern anomie. Regan thinks a little more midday socializing might set us straight. “It’s really tough,” he says, “to get angry with someone you’re breaking bread with.”

These things go in cycles, though. Maybe the city’s overstimulated workforce will one day realize it’s less efficient to spend 12 hours a day gabbing with colleagues on Slack than it is to work without distraction for half that time and take a proper lunch break. And sure enough, a handful of players—old and new—are waiting out the storm. Take the Bristol, in the Four Seasons. The Bristol’s clientele overlaps almost completely with Davio’s—for example, Connors feels “comfortable” there, too—but the restaurant is arguably more elevated. The bar is sexier, the food service more sophisticated, the interior design more refined. And then there are those windows, which open onto Tremont Street and the Public Garden, offering the best people-watching in the city. Crucially, it makes no concession to any of the contemporary trends I’ve spent this article talking about.

A couple of days after lunching at Davio’s, I meet Bill Taylor, the British-born GM of the Four Seasons. We’re seated by the window, just west of the row of eight power tables typically occupied by the restaurant’s elite clientele. Taylor’s wearing a dark suit, French cuffs, and rounded, wood-frame specs. Eager to play the part of the sophisticate, I arrive in a forest-green linen suit I’ve worn once in my life and immediately order an $18 glass of Sancerre. (Once again, nobody else in the restaurant seems to be drinking.) The place isn’t quite hopping on a summer Thursday, but Taylor seems immune to the suggestion that his restaurant is out of step with the times. “I don’t think we have ever in our history been an option for people to come to as opposed to going to their office cafeteria,” he says. “You’re not coming here or going to Panera Bread.”

Indeed, while it may not have the warmth of Davio’s or the clubbiness of Abe & Louie’s, the Bristol has a grandeur that’s hard to beat. Last year, Ed Kane and nightlife impresario Don Law teamed up to create Hub on Causeway, the massive bowling alley cum concert hall at the site of the old Boston Garden that’s set to open in 2019. They met to discuss the deal, many times, at the Bristol. “When you’re trying to close something, it’s the right place to do it,” Kane says. “I kept thinking that the space, and the Four Seasons, really matched Don’s personality—refined yet understated, warm and comfortable. No lie, I can still see him walking through the room. A very cool legend.”

This relates to Taylor’s general point: that lunchers tempted by the siren song of fast-casual aren’t Bristol people to begin with. I have no idea if this is true or not—both John Fish and Connors also seem fond of one particular hot dog stand in Southie—but Taylor’s attitude seems like a smart one. While everyone else in town is hustling to curate a poké bowl, it’s the Bristol’s $25 Grafton-cheddar cheeseburger with cognac-bacon-and-onion jam you’ll go for when the words power lunch inevitably come back into fashion. When I ask Taylor if anybody ever orders food to go from the Bristol, he looks at me like I’ve farted, and slowly shakes his head no.

He might be onto something. In November 2015, the UMass Club moved its moribund headquarters from the Financial District to the top of One Beacon Street, and installed its restaurant on the 32nd floor. Proximity to the State House, plus stunning views, made it an instant hit with the city’s politicos. Since the move, membership has nearly doubled, from 880 to more than 1,600. Governor Charlie Baker, Senate President Stan Rosenberg, House Speaker Robert DeLeo—all of them are in the club. Rising-star state Senator Linda Dorcena Forry eats there, as do old-guard consultants Chuck Campion and Michael Goldman. “On any given day, we could have a half dozen different VIPs in there,” all of them candidates for the restaurant’s most desirable table, says club GM Dave Eichstaedt. Lobbyist Phil Johnston says that he and Rosenberg come for dinner once in a while: “He likes to look at the sunset.” Eichstaedt, though, is clear on which meal draws the biggest crowd. “Breakfast is rather quiet. And of course we have a beautiful 14-seat bar that overlooks Charlestown,” he says. “But lunch is definitely our busiest period. No doubt about it.”

Still, for a glimpse of the future, it’s probably best to finish where we started, at homey Davio’s. It may not be foodie heaven, and if we’re being frank, the faded upholstery could use a refresh, but in one big way, it’s ahead of the curve. A few years ago, DiFillippo opened a to-go lunch counter off the back of his kitchen. It’s open from 7 a.m. to 4 p.m., serves 300 cups of coffee a day, and brings in $1 million of revenue a year. “I’ll see Steve Karp in here for a meeting at lunch,” DiFillippo says, “and I’ll see him out there having a chicken-salad sandwich.” Either way, he’s still eating at Davio’s. And DiFillippo will raise a glass of iced tea to that.