The Invisible Man

Inside Doyle’s Cafe, the venerable Jamaica Plain pub once described by the New York Times as “a century-old citadel of Irish politics,” there is an especially shrinelike corner known as the mayor’s table. Here, due homage is paid to the holy grail of Boston politics: the mayoralty. There’s a framed photograph of the city’s three living emperors, former mayors Kevin White and Ray Flynn, and current incumbent-for-life Tom Menino, together at the bar. Alongside hangs a framed Boston Globe front page documenting Menino’s election to his first term in 1993. “IT’S FOR REAL—MAYOR MENINO,” reads the headline. It’s a private, slightly elevated spot, an honored perch that resonates with the memory of campaigns past, sacred ground on which momentous political issues and strategies have been debated by the premier politicians, journalists, and consultants of their times. And smoking is absolutely not allowed.

Unless, that is, you’re a contrary old bastard like Ed Jesser, the undisputed king of political strategists in a city where political strategizing is a major sport. In his customary perch at Doyle’s, humbly attired in a Salvation Army outfit of gray-and-white-checked pants with cuffs, a gray shirt and a gray tweed jacket, topped with a white beard and graying comb-over, the 59-year-old Jesser is, in the phrase of his old friend and client Menino, “an unmade bed.” But his dog-eared appearance hides the literate intellect of a voracious reader, jazz pianist, and above-average golfer who, to put this literate streak in proper perspective, delights in shouting insults at other golfers as they go into their backswing. And like the city whose politics he understands better than any competitor, Jesser’s rumpled exterior masks a uniquely independent and incisive political sensibility.

While awaiting dinner one recent weeknight — bacon, lettuce, and tomato on white bread with fries, washed down with a Bass Ale and lungfuls of cigarette smoke — Jesser lights one Winston after another, flicking the ashes directly onto the hallowed wooden floor while animatedly discussing his latest triumphs: the runaway victory of South Boston state Senator Stephen Lynch in the Democratic primary for the late Joe Moakley’s Ninth District congressional seat, and the slam-dunk reelection of Menino to a third term, scheduled to be certified by the voters on November 6.

A turning point in the Ninth District fight, Jesser is explaining, was reached when Milton state Senator Brian Joyce identified Lynch during a televised debate as a “recovering alcoholic,” something Lynch had never publicly acknowledged. “I wanted to whack him,” the master consultant recalls. “And then I snapped back into thinking, How does this play?” Preserving the privacy of participants is the cardinal rule of Alcoholics Anonymous. “A third of the fucking district are that way, and they’re not gonna like him bringing it up,” Jesser notes with a scornful laugh at the thought of all those recovering alcoholics shaking their fist at Joyce’s image on their television screens.

Another break for the Lynch campaign, says Jesser, was Needham state Senator Cheryl Jacques’ improbable attempt to paint the usually soft-spoken, populist former ironworker as an antiabortion radical Republican zealot. “How politically incompetent” of Democrat Jacques to attack Lynch over an issue on which many voters abhor ideologues of either stripe. “On one side, you got hairy-legged, fuck-all-men types who want to see babies taken out in the ninth month,” snorts Jesser. “On the other, big, fat Irish women who never get laid. They both suck, so you pick one on the basis of your personal moral beliefs. How foolish.”

As for Menino, set to crush Boston City Councilor Peggy Davis-Mullen in his easy bid for reelection, Jesser is despondent at the prospect of not getting to lower the boom on her with a TV ad campaign touting the mayor as the city’s benevolent grandpa. Davis-Mullen’s campaign is too anemic to bother. “We’ve got a great spot with the five grandkids in it, beautiful fucking pictures, and we can’t even fucking use it!” Jesser moans.

Cynical, profane, politically incorrect. You’d better have parked your effete sensibilities at the door if you’re going to survive your trip to Jesser World, where the cigarette ash piles up on the floor, the greasy fries disappear, and the acerbic quotes pour out. It’s an obscenity-laced ride, a tour of both the idiosyncratic style of Boston Irish-Catholic Democratic populism and its most striking contradictions: narrow parochialism coexisting with expansive compassion, the persistent grudges and the enduring loyalties, the caring and the cursing. For all of this, Jesser is almost unknown to the public, a shadowy character who is the top adviser to the mayor, yet almost never consents to interviews and avoids being photographed. “He represents Boston in all of its contrasts,” says John Moffitt, regional head of the federal Small Business Administration during the 1980s, when Jesser did public relations work during a fallow period in his long political consulting career.

These days, business couldn’t be better. With cash flow assured from business clients that have included Cablevision and John Hancock, and from wife Connie Kastelnik’s thriving communications consulting operation (how much he makes is “none of your fucking business,” he says, when asked), Jesser often waives his fee, choosing to help a candidate “because I think I ought to.” Lately, these tend to be the same candidates the electorate winds up thinking it ought to vote for. To watch Lynch, rocked early in the campaign by damaging disclosures about nonpayment of student loans, glide home in a tough race without a single misstep, was to see the genius of Jesser’s media savvy and instinct for the voters’ mood. It was only the most recent triumph in a career that’s produced winners in presidential primaries (Jimmy Carter in 1980, Paul Tsongas in 1992), mayoral races (Ray Flynn and Menino), and everything in between.

“He’s unique, a throwback to the old days, like a character out of The Last Hurrah, but thoroughly modern too,” says Charley Manning, a Cambridge-based Republican consultant who just three years ago saw his client, attorney general hopeful Brad Bailey, obliterated by Jesser’s candidate, Tom Reilly. “When you think of political operatives, you think of the little smeechies running around in a suit with the pin and the two cell phones. They’ve got no feeling for the soul of politics. But Eddie does.”

“I was taking sides at birth,” says Jesser. That’s what happens when you’re fourth in a family of six at the Old Harbor housing project in Southie. Jesser’s father, Tom, owned Eddie’s Bar on Meetinghouse Hill in Dorchester, and his son grew up in a world defined by parish, ward, and precinct. His first stint as a campaign volunteer came at the tender age of five, helping John E. Powers run for state rep, followed by work on John F. Kennedy’s 1948 congressional reelection bid, when Jesser’s job was to periodically open the back door of the campaign’s sound trucks and knock off any local urchins hitching a ride on the running board.

A diminutive child and a poor fighter with small hands, Jesser came to rely on his quick mind and sharp tongue. “I was a wise guy, the best ranker in the neighborhood,” he says, a reference to working-class Bostonian affection for the neatly turned insult, or “rank,” that can be a sign of affection or hostility, or simply the most effective way of getting through to a politician surrounded by bum-kissers and yes men. It’s a skill that has endeared Jesser to the diverse array of political figures he’s helped over the years, from moralizing liberals such as Tsongas and Carter to streetwise pragmatists including House Speaker Tom Finneran and Menino. “What have I learned from him? How to keep my mouth shut,” says Menino.

That’s a lesson Jesser absorbed himself during a checkered academic career that included invitations to leave Boston College High School and Boston Latin due to “disciplinary problems.” Over Bass, butts, and a plate of cholesterol at Doyle’s, Jesser’s opinions are unbridled. But it’s unlike the passion of the ideologue, a breed the self-described “lunch-bucket liberal” detests. “The purity of their ostensible beliefs is far more important than helping people, like these total fucking fools on the streets protesting the war [on terrorism],” he says.

Jesser has no use for the right wing either. He says the low point of his career was Richard Nixon’s landslide victory over George McGovern in the 1972 presidential race. “Me and Mary McGrory were the only two people left who just couldn’t fucking believe that this fucking lowlife could win,” he recalls. Yet he reserves special scorn for the left — scorn that comes from knowing it well. After “14 fucking months” helping the McGovern campaign in ’72, “I know liberals the purity, the self-certain purity of that breed of liberals, none of whom ever worked for a living.” One of Jesser’s proudest accomplishments, he says, was burying Ted Kennedy’s challenge to Carter in the 1980 Iowa caucuses. “What bothered me about Teddy was, he was the moral force for liberalism running against the den of iniquity that was James Earl Carter,” says Jesser, with maximum sarcasm. “I don’t like ideologues.”

Indeed, Manning says he’s “never really heard Ed discuss ideology.” That doesn’t mean it’s altogether absent. Jesser returned from a 22-month involuntary military stint in 1967 with profound hatred for the Vietnam War. And he retains a lifelong concern for the elderly, a focus that surfaces in the emphasis of the campaigns with which he is associated. “When they can’t do it anymore, we gotta do it, and we gotta cough up whatever it takes to do it,” he says, observing contemptuously that the Jacques campaign never ran a TV spot showing where she stood on elder issues. “Nothing about seniors? That’s the first fucking thing you talk about.”

But a few overriding themes aside, all politics for Jesser, as it was for Tip O’Neill and other giants of a certain era, is local. And personal. Like any good Bostonian, Jesser prefers the company of Democrats. Once, at a Kennedy School reception for former Republican U.S. Attorney General Richard Thornburgh, Jesser informed a presumably startled Mrs. Thornburgh that, no, he didn’t want to talk politics with her because “your husband’s a Republican and he sucks.” But the occasional Republican is welcome in Jesser World, especially if he or she is a sworn enemy of Jesser’s own arch nemesis, former Mayor Kevin White.

Jesser, who helped Joe Timilty in his three epic mayoral races against White in the 1970s, blames harassment by White’s police force political payback for his own role in those Timilty campaigns, he says — for the death of his father, Tom, from a series of heart attacks. In 1975, when he was a spokesman for Timilty, Jesser criticized a police official who was close to White. In retribution, he says, the police cracked down on his father’s bar, prompting Jesser senior to suffer two heart attacks. The second one was fatal. (White did not respond to requests for comment on this issue.) So convinced is he of White’s role in his father’s death that, almost 10 years after then U.S. Attorney William Weld dragged White through a lengthy corruption probe, Jesser found the time to help Weld run for governor in 1990. “Post hoc, ergo procto hoc,” explains Jesser. After this, on account of this.

Grudges aside, Jesser succeeds because his pragmatism is never overwhelmed by ideology or cant. He displayed what Moffitt calls his “practical Bostonian side” early on during his days as a night attendant at the old Boston State Hospital, when he propped a corpse up in a chair next to the radiator to keep it warm so that the death would not be traced to his shift. But in a business of mercenaries and front-runners, the trait that links Jesser most closely with the culture that spawned him is his understanding that no matter how busy you are fighting your enemies, you never forget your friends.

“The most perfect attribute which every person should try to possess is loyalty,” wrote eighth-grader Ed Jesser in Sister Florentine’s class at St. Margaret’s. “This is a very needed virtue.” But even back then, there was an undercurrent of realism flowing through Jesser World. “Loyalty strengthens our character,” he wrote, “depending on how often we use it.”