Photo: Troy Word/CPI

If everything works out, it may be the last great political deal brokered in a smoke-filled room. On a balmy June night in 1999, Judith Nathan was having a drink at Club Macanudo, a cigar bar on East 63rd Street. Her companion was Dr. Burt Meyers, an infectious-disease specialist at Mount Sinai hospital and one of the many physicians she had befriended as a hospital sales rep for Bristol-Myers Squibb. Nathan, then 44, was at ease amid the upmarket manliness, a woman of the world among many middle-aged men of the world, including, that night, the mayor of the City of New York, Rudolph Giuliani.

Club Mac, with its wooden Indians, leather sofas, and “state-of-the-art ventilation system,” had become a well-known late-night haunt for the mayor. Perhaps it was also something of an escape: He was still living at Gracie Mansion with his second wife, television personality Donna Hanover. Here, he could kick back with a tumbler of Glenlivet and relax with City Hall aides and political associates. Sometimes a woman would approach him, interrupting his cigar-smoking to express her admiration, maybe get an autograph. Perhaps flirt mildly. So it wasn’t surprising when Nathan, a pretty woman with rich brown hair, came over and said hello.

This story of how they met had to be pieced together from accounts by Giuliani intimates because the couple refuses to talk about it. Even during their gauzy TV interview this past March with Barbara Walters—who was a guest at their wedding in 2003—which was a custom-made moment to safely peddle this type of personal anecdotage, Judith demurred. “That’s one thing I would kind of like to keep private,” she said, allowing only that “it was by accident.”

A few days after their fateful meeting, the mayor had an aide retrieve Judith’s business card from his desk drawer at City Hall, then he phoned and asked her out. They took in a movie at Loews Kips Bay, The General’s Daughter, which is about a cover-up at West Point. At dinner afterward, at Peter Luger Steakhouse, they were chaperoned by a couple of City Hall staffers.

Later, on the occasion of their marriage, Giuliani would tell the Times’ “Vows” columnist that “our attraction was instantaneous. There was something mystical about the feeling.” He evoked an appropriately operatic moment from one of his favorite novels, Mario Puzo’s The Godfather, when Michael Corleone spotted his Sicilian bride, Apollonia. “It was,” Rudy said, “the thunderbolt.”

When she met the mayor at Club Macanudo, Judith Nathan couldn’t have imagined the complexity of the relationship she was getting into. At that point, the considerable successes of Rudy’s mayoralty were in the past and his future was uncertain. He may have looked like a catch, but he certainly did not look like a potential president. There was talk of a Senate run. Now, in a Cinderella-like reversal, Judith Giuliani, with her husband’s help, is auditioning for a vast and contradictory role: romantic partner of America’s Mayor, wholesome third wife, definer of gender roles, and emblem of respectable femininity for an entire nation. So far, her attempts to play this impossible part have been riveting, if sometimes comic.

Rudy Giuliani has always been the most insular of politicians, operating within his personal tribe, at odds with most everyone outside. The prime value is extreme loyalty, and for those in possession of that quality (think Bernard Kerik), much else is forgiven. Like George W. Bush, he and his team create their own reality and wait for the world to follow.

Judith Giuliani is the latest to join this coterie, and by far the most important. He’s given her influence into all facets of his professional life. He has often referred to Judith as his “closest adviser.” In a 2003 TV interview, Rudy claimed that Judith is “an expert we rely on” at Giuliani Partners. “She gives us a lot of advice and a lot of help in areas where she’s got a lot of expertise—biological and chemical,” Rudy said as Judith watched him and nodded vigorously. “And since we do security work, that’s an area of great concern—you know, another anthrax attack, a smallpox attack, chemical agents. She knows all of that.” Famously, he told Barbara Walters that Judith would be able to sit in on cabinet meetings, acting at the time as if this were a perfectly ordinary responsibility for a president to give his wife.

At other times, their presentation has been lovey-dovey to the point of queasiness. Their displays of affection got so gooey during the taping of the Walters interview that the ABC News doyenne is said to have joked, “Enough already!” They held hands and cooed; he called her “baby” and she called him “sweetheart” as they kissed on the lips. At one point, after he absolved her of responsibility for his divorce from Hanover and his alienation from their two children (“She’s done everything she can. She loves all the children”), Judith, who was serenely feminine in a sea-green sweater, with another, lavender sweater tied casually around her neck over it, French preppy style, reached out to caress his cheek. When Walters asked her if she was “bothered” by her affair with the married mayor, Judith responded, blandly, “It was a rocky road, absolutely. But when you have a partnership that is based on mutual respect and communication, the two of you know what’s going on.”

Americans have an unresolved relationship with their idea of what a First Lady should be. It doesn’t usually involve thunder and lightning. Political consultants know what’s easiest to sell: Harriet Nelson, which is to say more or less Laura Bush. More-assertive types, be it the Svengali socialite in couture (early Nancy Reagan), the defiantly unkittenish liberal crusader (early Hillary Clinton), or the aloof and foreign-seeming heiress (Teresa Heinz-Kerry), are more off-putting because it’s difficult to identify with them.

Judith Giuliani’s biggest drawback—her three marriages—reminds voters of Rudy’s own three and the associated tawdry drama. The first, to his second cousin, was annulled after fourteen years. His second, to Hanover, ended with Rudy’s televised May 2000 announcement that he intended to separate from her; Hanover’s shocked, tearful, also-televised response blamed Rudy’s “relationship with one staff member,” i.e., his communications director Cristyne Lategano. That was before much was known about Judith. By the summer of 2001, Judith’s face, along with Donna’s and Rudy’s, was plastered on the cover of People magazine with the tawdry headline INSIDE NEW YORK’S NASTIEST SPLIT … THE MAYOR, THE WIFE, THE MISTRESS.

Six years later, the rollout of Judith-as-wife, as potential First Lady, is still tainted by the smoke of that thunderous extramarital night at Club Mac.

Her magazine appearances have tended to be like the one in the March Harper’s Bazaar, where she talked about “making him happy, making a happy home” and posed lip-to-lip on Rudy’s lap. “I’ve always liked strong, macho men,” she told the magazine. “Rudy’s a very, very romantic guy; we love watching Sleepless in Seattle. Can you imagine my big testosterone-factor husband doing that?” But amid their efforts at cozy public normalcy, suddenly Rudy’s son, Andrew, told a Times reporter that “there’s obviously a little problem that exists between me and his wife.”

Theirs is a very New York love story, complicated and, frankly, mature. It’s hard to say how it’ll play in the red states.

In early 2000, as Rudy’s Senate race was getting under way, Judith Nathan was a mysterious but constant presence in the campaign entourage. Rudy didn’t bother to clarify her role internally, and the few people in the know kept their own counsel. One campaign staffer at first assumed Judith was “some sort of adviser or consultant.” Others believed she was a member of his security detail. Finally, by the time Rudy withdrew from the race in May, most folks had figured it out.

The couple was quickly beset by crises: his prostate cancer and then 9/11.

Under Judith’s guidance, he considered various treatment options and decided against surgically removing the prostate—the method that produces the most reliable outcome—in favor of implanting radioactive seeds. Called brachytherapy, it’s a less common procedure that has its advantages: The risk of long-term erectile dysfunction is lower. “He didn’t want the knife down there at all,” says an intimate who was privy to Rudy’s worries.

Meanwhile, Rudy’s divorce lawyer, Raoul Felder, acting on his image-battered client’s instructions, announced that Rudy’s radiation treatments had for the past year left him impotent, making sex with his girlfriend impossible.

“Part of the reason Rudy loves her so much is that she loved him, and batted her eyes at him, even when his very virility was questioned, when his sexual vitality was knocked out,” says the former Giuliani associate.

And Giuliani was unquestionably in love.

A few years ago, at a wedding attended by prominent lawyers and judges, Rudy and Judith were sitting at a table where the other guests were having a spirited legal and political discussion. “Rudy was deferring to her the entire evening,” says a fellow guest. “They were talking about the war in Iraq, and she was opining. They were talking about the Second Circuit, and she had an opinion about that too. People didn’t know what to say. And Rudy, if anything, was drawing her out. ‘What do you think about that, baby?’ She likes to talk.”

A former associate of Giuliani’s from the days when he was a mob-busting federal prosecutor says, “Loyalty does mean everything to him. He absolutely adores her. He doesn’t need the expensive Brioni suits she has him wear, or the fancy food she has him eat. He was a cheeseburger-and-martini guy. But Rudy defers to her.”

Almost immediately after they came out as a couple, Judith accompanied the mayor everywhere, even marching alongside him in city parades. Paparazzi staked out her apartment building and her condo in Noyack. Donna Hanover obtained a court order barring Judith from Gracie Mansion.

She quit Bristol-Myers Squibb in March 2001 and, with the connections supplied by her powerful consort, joined a philanthropic consulting firm, Changing Our World Inc., as a managing director.

Before they were married, he indulged her desire to dine regularly at Le Cirque even though the heavy cuisine tended to make him queasy. “It was almost required daily, going to Le Cirque for dinner, and Rudy used to throw up afterward, because the food was so rich,” says a witness. “But she wanted to go, because it was the place to be seen, and the treatment by Sirio [Maccioni, the owner] was incredible.”

As you descend from the hilltops on Route 309 into the former Judi Ann Stish’s hometown, Hazleton, Pennsylvania, it sparkles like shards of glass in the sunlight. Then—closer in, on the edge of town—the vision loses its luster amid the detritus of a long-abandoned coal-mining economy. You pass a barnlike structure sporting a sign that misspells adult shope, then gigantic Quonset huts, then strip malls, then churches. Since the mines shut down after World War II, Hazleton has struggled mightily. In 2002, U.S. News & World Report labeled Hazleton “a town in need of a tomorrow.” Aside from Judi, the city’s most famous native is Jack Palance.

Judi’s second cousin, retired Hazleton Area schools superintendent Geraldine Stish Shepperson, says the family patriarch—whose surname was Americanized from Sticia—emigrated from Italy to toil in the mines with Irish and Slovak settlers in the early 1900s. “They were all poor working people.” Judi’s grandfather Frank Stish, a milkman, was paralyzed in an on-the-job accident, Shepperson says, and Judith’s 81-year-old father, Donald, is a retired circulation manager for the Philadelphia Inquirer. Judi’s mother, Joan, is Polish-American, and these Stishes—including Judi’s older brother, Donnie, and younger sister, Cyndy—attended St. Stanislaus Catholic Church, down the street from their modest two-family house on Carson Street in the Nannygoat Hill neighborhood. These days, Donald and Joan Stish spend part of the year in a Palm Beach condo purchased by Rudy and Judith.

“She was beautiful and had long, reddish hair,” remembers current Hazleton High School English teacher Mike Saleeba, who was a year behind Judi back in the early seventies. “I remember her face—she had a fantastic complexion. I wouldn’t have dared to ask her out.” Still, “she would go out of her way to say hello to you. She wasn’t one of the snobs.”

Saleeba compares Hazleton’s atmosphere in those days to the sitcom Happy Days. Saturday nights were spent dancing to live bands at the local YMCA. Afterward, the kids headed for the Knotty Pine—“the Pines,” they called it—a popular diner where they pulled up in their cars, flashed their headlights, and the waitresses served barbecue sandwiches curbside. Judi’s Hazleton High classmate Mike DeCosmo often dropped her home after a night of fun. “She was one of those people who never had a bad word about anybody, always upbeat, always friendly,” says DeCosmo, today an accountant.

Judi was known as a diligent student and an attractive girl who busied herself with extracurricular activities such as the Future Nurses Association, the tennis and ski clubs, the literary society, and the Diggers Club, a volunteer service organization that “brightened the days of many handicapped and retarded children in Hazleton’s schools,” according to Janus, the high-school yearbook.

In a blue-collar place like Hazleton, nursing was one of the few professions that were seen as appropriate for young women. “There was teaching, and there was nursing. That’s all that was offered to us, really,” says the school librarian, Theresa Krajcirik.

It also got Judith out. She met medical-supplies salesman Jeffrey Scott Ross and, after two years of nursing school up the road in Bethlehem, married him at the Chapel of the Bells in Las Vegas. Then they moved to North Carolina.

Their marriage lasted less than five years. By the time of their uncontested Florida divorce on November 14, 1979, husband No. 2 was already in the wings. She married Bruce Nathan five days later.

They had met in Charlotte, where Bruce had moved after selling the Long Island–based office-furniture business founded by his grandfather. For the 24-year-old Judi, who had spent much of the previous five years on the road, demonstrating and selling surgical equipment, Nathan was a catch. Over the course of their increasingly rocky marriage, they lived in Atlanta and Manhattan (while acquiring a Hamptons summer place) and the Pacific Palisades in Los Angeles. She left him and moved to New York in March 1992 with their 7-year-old daughter, Whitney.

Not surprisingly, Bruce Nathan’s friends remember Judi less than fondly. “She was a real opportunist, a real Becky Sharp character,” says a Nathan-family friend who shared Thanksgiving dinners with Bruce and Judi. “She was kind of cute, and Bruce was quite handsome—a rich trust-fund kid from Long Island. She was less sophisticated in those days. I think she really desired to be sort of the Junior League type. She basically struck me as having an inflated, self-important view of herself.”

Photo: Diane Bondareff/AP

The voluminous divorce papers filed with Los Angeles County Superior Court paint a more complicated picture. In public court documents, Bruce said he and Judi adopted Whitney in March 1985, when they lived in Atlanta, after trying for five years to have a child on their own. In 1987, they moved to New York, renting a series of apartments on the Upper East Side. The formerly Catholic Judi became an active member of the socially prominent Brick Presbyterian Church. The Nathans enrolled Whitney at the elite Madison Avenue Presbyterian Day School and, later on, Spence. In other court documents, there is mention of a Porsche, a Cadillac, antique furniture, paintings, pricey rugs, a place in Southampton, and, according to Judi, Bruce’s “trust fund valued at $800,000 to one million dollars.” She added, “My husband has had a long history of credit loans to support his lavish lifestyle.”

As with all bad marriages, there seems to have been enough blame to go around. In one of the many affidavits filed and cross-filed by the warring Nathans, Judi accused Bruce of “a violent temper,” “numerous physical assaults and manhandling of me,” including “screaming vile epithets, cursing,” and “punching me in the side of my head” in March 1992. After that alleged attack—which Bruce has denied—Judith retreated with her daughter to a neighbor’s and called the cops. “I feared for my safety and that of my daughter,” she claimed in her affidavit, adding, “I immediately fled California.” She went first to Hazleton and stayed temporarily with her parents, then moved in with friends in Manhattan and took a part-time job in a dentist’s office before eventually finding full-time work at Bristol-Myers Squibb.

Bruce, in his own court filings, claimed that Judi had kidnapped their child and branded her an “unfit mother” and a “social climber” whose “‘main goal’ in life was being involved with whatever was ‘the in thing’ at the moment. Whether it was belonging to ‘the right church’ by converting from Catholicism to Presbyterian; playing bridge with the ‘right people’ … enrolling Whitney at the ‘right schools’ in order to further my wife’s social aspirations; wearing designer clothes and jewelry; and vacationing at the fashionable Hamptons.”

And while “I maintained my Jewish heritage,” Bruce alleged that “my wife thought nothing of physically and mentally abusing me within Whitney’s earshot.” When he couldn’t afford something, she referred to him as “Jew boy” and other slurs. Mike McKeon, Judith’s campaign press secretary, dismisses the “ridiculous” fifteen-year-old allegation. “Anti-Semites don’t marry Jews.”

Meanwhile, she went on with her life, having various romances. One is said to have been with a French diplomatic staffer. For four years, she and Whitney and clinical psychologist Manos Zacharioudakis lived together in a one-bedroom apartment on East 55th Street.

Years later, after Rudy made Judith the third Mrs. Giuliani and launched his campaign for the Republican presidential nomination, Zacharioudakis rhapsodized to the Daily News about his former lover’s “passion,” “sensual” nature, and “Italian eroticism.”

Around the same time, Judith went back to court over custody arrangements for 16-year-old Whitney. She’d fled her mother’s Upper East Side apartment to move in with her father, safely out of the limelight.

Then 9/11 happened, and everything changed. For one thing, Rudy’s political career was resuscitated. During his illness, Giuliani had become increasingly dependent on her, a relationship that continued into his professional life. “She had to approve his schedule, which had already been finalized weeks before,” says an insider. “People eventually knew not to lock anything in until she’d looked at it.”

In his best-selling 2002 autobiography, Leadership, Giuliani wrote that his future wife had been an effective mayoral adviser after 9/11 because she “had been a nurse for many years, and afterward a pharmaceutical executive; she had managed a team of people and had many organizational skills. Further, she had wide-ranging scientific knowledge and research expertise.” He added that he “put her to work helping me organize the hospitals” to treat the injured from ground zero. His campaign Website, meanwhile, notes, “In the aftermath of the September 11, 2001 terrorist attacks, Mrs. Giuliani coordinated the efforts at the Family Assistance Center on Pier 94.”

But concerning Judith’s participation in the city’s response to 9/11, public-health and security consultant Jerry Hauer takes exception to the Giuliani campaign’s assertions. Hauer—a nationally known bioterrorism expert who was Rudy’s first director of the newly created Office of Emergency Management—minced no words about the claim that the mayor’s then-girlfriend “coordinated the efforts at the Family Assistance Center on Pier 94.”

“That is simply a lie,” Hauer tells me. “But Rudy’s not shy about rewriting history when it suits him.”

Hauer had a bitter falling-out with Giuliani after Hauer endorsed Democrat Mark Green’s mayoral candidacy in 2001. “You’re done,” Rudy told him ominously after he and former police commissioner Bill Bratton staged a press conference endorsing Green.

Photo: Erik C. Pendzich/Rex USA

“I had left city government before 9/11, and Rudy called me back to help out,” Hauer says. “He asked me to relocate the Family Assistance Center from the Armory on Lexington Avenue, which was too small, to Pier 94. We put it together in two and a half days. At that point, he had already announced his separation from Donna and he wanted to get Judith involved somehow. Most people didn’t really care. We had a job to do. Where she had opinions, she offered them, and where they were valuable, we listened. The fact that she was the mayor’s girlfriend didn’t carry a lot of weight with most of the folks working there.”

Afterward, Rudy installed her on the board of the Twin Towers Fund.

The Giuliani-Nathan nuptials were a star-studded extravaganza at which the bride wore a bejeweled Vera Wang gown and a diamond tiara, Mayor Michael Bloomberg officiated, and the 400 guests included Wang, Walters, Beverly Sills, Yogi Berra, Joe Torre, Donald Trump and Melania Knauss, Rupert Murdoch and Roger Ailes, Mort Zuckerman and Henry Kissinger, even Cristyne Lategano-Nicholas.

Judith elevated her profile in the charity world by touting various good causes in her column in Gotham magazine. She lent her name to the all-girls Mother Cabrini High School and the McCarton School for autistic children.

In 2003, Judith posed in a cranberry bejeweled Carolina Herrera gown for the cover of the society glossy Avenue. She sported a huge Chopard brooch and Jimmy Choo shoes while reclining languidly in her so-called Moroccan sitting room. From the magazine’s excitable perspective, the Giulianis had “created their own Chartwell,” the name of Sir Winston Churchill’s country house, on the Upper East Side. The article confidently predicted that Judith “could be the most stylish First Lady since another Upper East Sider, Jacqueline Kennedy.”

“You have a successful marriage when you have each other as a priority,” she told the magazine. “I travel with Rudy. He respects me and involved me in all aspects of his life. We get involved in speechwriting. We make decisions together about which places we are going to go. It’s a busy life and we live it together.”

They have adjoining offices at Giuliani Partners at 5 Times Square, where she has installed Pilates machines, the better to keep her husband fit. Today, she doesn’t like to leave his side, her arm possessively around his waist at social gatherings such as a buffet dinner last July at Ronald Perelman’s East Hampton estate, where I saw the two of them navigating the A-list crowd joined at the hip. Manhattan hostesses have long known that if they invite the Giulianis to dinner, they must be prepared to breach protocol by seating them not only at the same table but next to each other, and Rudy’s standard lecture contract explicitly requires that his wife be placed beside him in case his appearance involves sitting through a meal.

It’s no surprise to veteran Rudy watchers that in recent weeks, senior presidential-campaign operatives have apparently been grumbling about what they consider Judith’s meddling in matters outside her areas of competence. “She’s, uh, feisty, as they say,” a high-level supporter told Newsday. “The staff people go a little nuts.”

The story of Manny Papir is a cautionary tale for anyone who doubts that Judith Giuliani is a force to be reckoned with. Papir, Rudy’s longtime personal aide, learned the hard way during a trip to Europe when Rudy, taking a 9/11 victory lap in early 2002, was knighted by Queen Elizabeth II and then was honored with the German Media Prize in Baden-Baden. Among Rudy’s inner circle, Judith was fast becoming known for her demanding requirements. Even loyalist Sunny Mindel was overheard joking that whenever they arranged a chartered jet for their principal and his companion, “we need two seats for Judith—one for her and one for her Gucci bag.” (“I have no recollection of saying that,” Mindel says.)

When Judith asked to stay two nights in Baden-Baden instead of the previously planned one—throwing the intricate schedule into disarray—Papir, who was advancing Rudy’s triumphal tour, made the mistake of betraying his impatience. Running into other members of the entourage in the lobby, he muttered, “Let me guess—you’re waiting for Princess, too.” When the quip was reported back to Rudy and Judith, Papir—who declined to comment—was out of a $200,000-a-year job.

McKeon dismisses the complaints, arguing that Judith is not trying to be a political strategist. “It comes from people who are not on the inside of the campaign. Maybe that’s why they’re grumbling,” he says. “Judith is nothing but an asset, and, as the campaign continues, she’s going to be a larger and larger asset.”

Her early work on the stump has been marred by occasional gaffes, but he calls her “an experienced public speaker” and says there are no plans to get her a speechwriter. “Her primary role is as a support system for Rudy in a personal way and as a character witness for him in a public way. She knows him as a man, as a husband, and as a good person, and that’s what she’ll be talking about. She’ll be one of our key surrogates.”

Judith Giuliani was introduced to the public by the tabloids. But that experience did not fully prepare her for the current one. Friends describe a woman who is hurt and baffled—“freaked out,” says one—by the barrage of coverage of her first marriage and the fact that long ago, her job had her demonstrating surgical-stapling procedures on live dogs.

Candice Stark, who’s known Judith for twenty years, believes that she’s a target of opportunity. “I read these things in the newspaper trying to trash her, trying to make her seem like something that she’s not, and I think it’s just people looking for anything they can to take Rudy down,” she theorizes. “Everything about his life is so well known they can’t dig much further, so they’re going after her instead. So much of politics is cruel. You’ve got to be strong.”

A confidant of Judith’s from the Hamptons, where the Giulianis paid $3 million for a 6,000-square-foot shingled house in Water Mill, complete with swimming pool, wine cellar, and cigar room, argues that she’s been unfairly caricatured. “This is a woman, a single mother, who has struggled most of her life, and she married somebody not because he was famous or because she thought he would be the president but because she was in love with him,” the friend says. “Now she’s very worried that something she will do or say will hurt his opportunity. She loses sleep over it. Reading in the newspapers that she’s a liability has been very, very hard for her.”

The friend added, “I think Rudy’s the one that’s sabotaging her. He’s out of control. There’s too much hand-holding and kissing on the lips, behaving like a couple of 18-year-olds in their first love affair. She doesn’t have the political smarts, and I don’t think she expected any of this.” (Like many people interviewed for this article, this friend asked for anonymity. “No good deed goes unpunished,” explained Howard Koeppel, declining to share his impressions of the mayor’s then-girlfriend, who was a frequent visitor after Rudy moved out of Gracie Mansion to bunk with Koeppel and his domestic partner, Mark Hsiao.)

Republican fund-raiser and Manhattan hostess Georgette Mosbacher—the ex-wife of Texas oilman Robert Mosbacher, who was Commerce secretary under the first President Bush—is a new member of Judith’s social circle, along with Walters and Beverly Sills. All three were Judith’s guests in December at an intimate ladies’ lunch at the Giulianis’ East 66th Street co-op off Madison Avenue. “It’s a tough role—I’ve been there,” says the flame-haired Mosbacher. “For me, it was horrible, devastating. You don’t want to hurt your husband, and everything you do reflects on him. You become hypersensitive and you try to be what you think the press wants you to be so they won’t come after you. But you learn pretty quick—at least I did—that you can’t win that way. In the end, you gotta be yourself.”

Judith, who had been Rudy’s constant companion during early campaign swings in New Hampshire, has more recently stayed behind and lowered her profile—and Rudy has urged reporters to cut her some slack, pointing out that “I am a candidate. She’s a civilian, to use the old Mafia distinction.”

When I ran into Rudy at the White House Correspondents Association Dinner in late April, he told me Judith skipped the event because “she’s up taking care of our daughter [Whitney] at Skidmore.” The locution “our daughter” was hardly calculated to repair his frayed relations with the biological children he shares with Hanover, especially 17-year-old Trinity-prep-school senior Caroline, who uses Donna’s surname and reportedly didn’t bother telling him when she was accepted recently by Harvard. (“In the next few months, Rudy really has to repair his relationships with Andrew and Caroline,” says a Republican strategist. “He can’t be the Republican nominee and have his kids estranged from him. That ain’t gonna cut it.”)

As for the brickbats Judith has been absorbing of late, “I tell her it’s just like when I was mayor and every day people want to disagree with your policies and criticize you,” he said. “Over time, you get used to it.”

Wren Abbott contributed research to this article.