Part 2 of 2
Like his brothers-in-law, Harold was a snappy dresser, usually attired in a
starched shirt, tie and hat. Relatives described him as an affectionate man, who
hugged as tight as a vise and kissed old ladies and children. Due to his stomach ulcers,
the gray-eyed, bespectacled bartender often drank milk while his customers
knocked back scotch. In case anyone got too rowdy, he kept a baseball bat behind
the bar and a .38 caliber pistol next to the cash register. An opinionated and voluble
Yankees fan in Dodgers land, a man who reputedly hated most politicians,
Harold would engage in heated arguments with his customers, his voice booming
sometimes out into the street. If there was a bar fight, it was Harold who broke it
up. If a customer had let his tab go for too long, it was Harold who went with his
baseball bat to collect.
But bar tabs weren't the only debts Harold collected. He had come a long way
since the spring day more than fourteen years ago when he mugged a milkman.
Now, the crimes he committed were part of an organized criminal enterprise.
Known as the "muscle" behind the loan-sharking operation, Harold was Leo's collection
agent, recouping money that had been loaned out and was now overdue.
Most debtors would pay at the bar, slipping an envelope to Harold across the
counter. In the mid to late '50s, Harold collected as much as $15,000 a week, tapping
dozens of debtors. The "vig" usually began at a stifling 150 percent and rose
with the passing of each week. Many people borrowed money to pay rent or foot
a business expense and would pay back four or five times the amount they borrowed.
There were no excuses for being late.
One afternoon, a man reluctantly entered the bar to apologize to Harold that he
didn't have the money-could he have just one more week? Frowning, Harold
reached under the bar and, out of sight, gripped his baseball bat. As the man before
him continued pleading for an extension, Harold swung the bat, cracking him
flat across the face, sending him back a few feet, according to an eyewitness. "Don't
be late again," Harold said.
That was the gist of Harold's job: Enforce Leo's law through threats or violence.
He shoved people against walls, broke legs, smashed kneecaps, crunched noses. He
gave nearby Kings County Hospital a lot of business.
"People in the neighborhood were terrified of him," said a frequent customer at
Vincent's, who was one of Leo's son Lewis's best friends and whose family borrowed
money from Leo.
He remembers what happened early one Saturday morning after his own father
failed to make a payment. "When I was a kid, my father borrowed money from
Leo," he said. "He couldn't pay, so Harold came to collect. He knocked on the door
and yelled, 'I want the money now, or I'm going to break both your arms!'"
After Harold calmed down, an agreement was worked out. "They talked to Leo
and straightened it out," he said.
While in high school, Lewis's friend did occasional chores around the bar, and
his brother took a job in the wire room, charting bets on the numbers boards.
Many years later, after opening his own business, Lewis's friend borrowed $90,000
from Leo and paid back $160,000-a fairly modest repayment total. "It would
only take me four to five weeks to pay him back," he says, adding that his brother
once borrowed $5,000 and ended up paying back $20,000.
Gambling, loan-sharking and booze weren't the only sources of income at
Vincent's. A black man who worked in the payroll office at a local hospital would
stop by the bar every week or so to give Harold several dozen fake paychecks. The
checks were made to out to a host of fictitious employees and were drawn on the
hospital's bank account. "Harold would cash them in the bar," said Lewis's friend.
"There would be several thousand dollars worth of checks every week. Harold
would get half, and the black guy would get the other half."
Vincent's Restaurant was frequented, from time to time, by a few prizefighters,
and Harold grew friendly with several. By some accounts, Harold even
managed a fighter or two. He once "bought fifty-fifty" into a boxer, according to
Gina Gialoreta. Robert D' Avanzo's son Steven recalled that "Harold managed several
fighters over the years." Elizabeth Mandelino also remembered Leo in a managerial
role. "Leo was going to help some guy who was going into training," said
Mandelino. But that venture never worked out.
Leo wasn't the only "connected" guy in Harold Giuliani's life who had a hand
in the boxing business. The burly bartender's lifelong best friend from his East
Harlem days, Louis Carbonetti, was a cutman for fighters-one of whom was
Italian boxer Vic Dellicurti. A middleweight fighter who went to the mat with
Sugar Ray Robinson four times, Dellicurti was widely known as a human punching
bag, a magnet for blows. Living on the third floor of Carbonetti's building at
325 East 10Sth Street, the thick-skulled palooka likely landed more blows on his
wife than on any opponent in the ring. "He would beat the shit out of her," recalled
Carbonetti's son, Lou Carbonetti Jr.
Dellicurti was controlled by Jimmy White, a notorious mob manager with an
impressive arrest record. Charged, at various times, with murder, robbery, larceny
and white slavery, White did a healthy dose of time and broke out of prison twice.
Carbonetti, whose tentacles extended into several spheres of influence, was also
the personal secretary to State Supreme Court Judge Thomas Aurelio, the most notorious
mob-tied judge on the bench in Manhattan. Aurelio's name hit the headlines
when his voice was picked up on one of the first wiretaps, placed on the phone
of the city's most famous mobster, Frank Costello, known as the Prime Minister of
the Underworld. Clad in custom-made suits, chomping on English Oval cigars,
Costello engineered Aurelio's 1943 nomination to the Supreme Court. When
Aurelio called Costello at home to thank him, Costello offered his congratulations
and then added: "When I tell you something is in the bag, you can rest assured."
District Attorney Frank Hogan made the tape public-an extraordinary revelation
at the time of how thoroughly mob influence had penetrated the judiciary.
Carbonetti was Aurelio's top aide-from the moment he took office-though
not a lawyer himself. A Democratic district leader from East Harlem, Carbonetti
was also a top supporter, in the early '50s, of Mayor Vincent Impelliteri, whose administration
was swamped with mob and scandal allegations.
Lou Carbonetti Jr. recalls that Harold would usually swing by the Carbonetti
residence for a beer and a weekend card game at the kitchen table. When Rudy was
older, his father would take him to meet Lou Sr. and Jr. for a Yankees game. Lou Jr.,
not a baseball fan, often protested. "I hated it," he said. "But my father would say,
'You have to go. Harold's corning all the way from Brooklyn.'"
In the late '50s, Carbonetti remembered waiting with his father and Harold
Giuliani outside a police precinct in Harlem late one night for Harold's younger
brother Rudolph to get off duty. Rudolph had just started at the precinct, and the
two were there to make sure he was OK.
Harold remained a close friend of Carbonetti's for most of his life. In 1952, more
than fifteen years after he had left Harlem, Harold bought an ad in Carbonetti's
clubhouse journal congratulating his buddy Lou on a good year. While most ads in
the journal were a quarter or half page, Harold's was a full page and listed at the
bottom not only his own name, but also Helen's and Rudy's.
In the early '50s, young white Brooklynites began flocking east to take part in
the subdividing of the Long Island frontier. A nascent demographic shift, blacks
moving into certain areas of Brooklyn, like Flatbush, spurred the migration. In
August 1951, sixty-nine-year-old Adelina sold 419 Hawthorne, enabling her
daughter, Harold and seven-year-old Rudy to live in a place of their own-far
away from changing Brooklyn. With Adelina's money, the family bought a quaint
two-bedroom Cape Cod house on Euston Road South, a somnolent, leafy street in
Garden City, Long Island. The title was listed in Helen's name alone, though
Adelina moved in with the Giulianis.
Rudy's new street was a changeless chain of nearly identical, squat, brick Cape
Cods, each with a maple tree spaced two feet to the right of the driveway. In the
summer the maples arched over the road, forming a lush canopy under which the
neighborhood children played stickball. The road surface was not made of asphalt
but rather of loose blue stone pebbles in which footprints and tire tracks were always
When the town of Garden City was founded in 1869, Harper's Weekly predicted
that it would become "the most beautiful suburb in the vicinity of New
York." More than eighty years later, in 1951, Garden City, cozily nestled in the
middle of Nassau County, had arguably earned that honor. A model "planned
community," with both quiet, tree-shaded streets and a gauntlet of ritzy city department
stores lining its main thoroughfare, it was a carefully manicured suburban
Shangri-La, the residential jewel in Long Island's crown. What Garden City
had also earned was a reputation for being one of the most elitist, homogeneous
and exclusive villages in all of Long Island. It was a Caucasian Christian cocoon,
with white Anglo-Saxon Protestants and Roman Catholics accounting for virtually
its entire population. As late as 1968, there was not a single black family. Jews
accounted for less than one percent of the population. The only two black students
in the school system at that time were both imported from the South via the
Urban League's Student Transfer Education Program-and, initially, the school
board refused to accept them, citing overcrowding problems. At the village's three
country clubs, there were no black or Jewish members. In 1970 when the Garden
City Unitarian Universalist Church proposed starting a day-care center for poor
minority children from neighboring areas, it was met with a fierce, visceral resistance
by area residents, including legal challenges.
The Giulianis made one immediate change when they left Brooklyn. On the advice
of his old East Harlem buddy, Lou Carbonetti, Harold and his wife switched
their voter registration from Democratic to Republican. "Harold had a friend in
Harlem who was a Democratic district leader," Helen said. "He told us that we'd
better become Republicans if we were moving to Nassau County."
Now sheltered from the diversity of Brooklyn, young Rudy's world view was
inevitably shaped by the uniformity of his new surroundings.
Unlike 419 Hawthorne, the Giulianis' new house had a basement in which
Harold installed a Ping-Pong table and model train set and strung up a canvas
punching bag filled with sand. In the living room, a new mahogany cabinet
housed an RCA television set. There were only two bedrooms; Helen and Harold
took one, and Rudy and Adelina shared the other. Soon after they moved in,
Helen decided that Rudy needed his own room, and Adelina, whose largesse had
made the purchase of this new house possible, was forced to sleep on the living
The neighbors were friendly but kept to themselves. That was the unspoken
code of Euston Road: Smile, say hello, mind your own business. Most Saturdays,
the men of the neighborhood would nod to each other across their fences as they
mowed their lawns or barbecued dinner.
From where the Giulianis lived, it was a convenient commute to Manhattan or
Brooklyn. The LIRR station was only six blocks away, as was the bus station. But
Harold, still tending bar at Vincent's, usually drove to work. Helen and her mother
stayed home, cleaning the house, looking after Rudy.
Halfway through second grade, Rudy enrolled at a nearby Catholic school, St.
Anne's, run by the nuns of the Order of the Sacred Heart of Mary. Built in 1950
to accommodate Long Island's recent influx of Catholic families, St. Anne's was a
brand-new, utilitarian brick building with a statue of its saint displayed prominently
out front. The student population was primarily Italian, Irish and German,
kids from lower-middle- and upper-middle-class families. Everyone was required
to wear uniforms, navy blue pants, a white shirt and blue tie. Each day began with
a prayer and the Pledge of Allegiance. The Cold War was on, and the nuns instructed
their pupils that Communists were godless and led them in prayers for
the capitalist and democratic conversion of Russia. The neophytes also learned
bible stories, studied the lives of the saints and memorized the ten commandments.
It was before Vatican II, and that meant meatless Fridays and Mass delivered in
Latin. Goodness required diligence and discipline. From the catechism, Rudy
learned a stark and unbending system that delineated venial sins and mortal sins,
sanctifying grace and actual grace. There were several types of prayers to memorize;
one could lessen your stay in Purgatory by five years, another, only by
three. Rudy and his classmates once studied a sketch of three milk bottles meant
to help convey the different levels of sin. The all-white bottle represented a soul
free of sin and ready for heaven. The bottle mottled with black spots symbolized
a soul blemished with venial sins and on the route to purgatory. Lastly, there was
the bottle the color of black ink, which flagged a soul damned to eternal damnation.
Joan Lipp, Rudy's former classmate and neighbor, recalled him as charismatic
and friendly, if a tad mischievous. "He was chubby and jolly," she said. "1 remember
the nuns saying 'Mr. Giuliani,' so he must have done something wrong, for
them to say that."
Rudy's newspaper route had taught him many of the roads in and around
Garden City. That business venture, however, was a financial disaster-Rudy apparently
routinely failed to collect his payments-and he eventually gave it up.
Without an encumbering stack of newspapers, the young teenager was now free to
peddle on his three-speed Schwinn bicycle wherever his fancy took him. One such
place was Klein's department store. Fourteen years old, Rudy parked his bicycle
outside one afternoon and ventured in. He thumbed through the 45 rpm singles,
through records by groups like the Platters and Bill Haley and the Comets. Out of
the corner of his eye, a sign proclaiming "SALE" beckoned him.
"1 saw a Julius Caesar album for 98 cents," recalled Rudy. Claiming that he
thought it was Shakespeare-he had begun studying Shakespeare in school-he
picked it up. He ended up buying George Frideric Handel's opera Julius Caesar and
Peter Ilyich Tchaikovsky's The 1812 Overture. He peddled home with his new
records and played them in his room. "1 followed the opera by reading the libretto
printed on the back of the album jacket," Rudy said. "1 fell in love with the record.
It was like a revelation."
Within a few days, he had bought Giuseppe Verdi's Rigoletto. An opera fan was
born. Since his father eschewed opera in favor of baseball and boxing, young Rudy
would usually sequester himself in his room and, like his grandfather Rodolfo, listen
to his opera records alone.
In 1953, the building in which Vincent's was located-together with other parcels
on the block-was condemned by court order and slated for demolition. Planning to
build a high school on the site, the city bought up all the property. Real estate documents
indicate that Leo's wife Veronica was paid $4,900 by the city for the property
and his brother Vincent got $3,250 for the "fixtures." Leo's bar was relocated five
blocks to the corner of Nostrand and Hawthorne, at 1203 Nostrand, just a block and
half from 419 Hawthorne. The property, still in Vincent's name, was on the first
floor of a three-story brick building that featured an incongruous Greek cornice trim
above the door. The bar remained a front for Leo's gambling and loan-sharking.
By the mid and late '50s, Harold had become irritable and distracted, according
to a few patrons at Vincent's. Sometimes, as a row of drinkers collected at the bar,
the stooped, brooding bartender would be absently wiping down the counter while
staring vacantly into the middle distance. When someone interrupted his daydreaming
to ask for a refill, Harold might snap at the drunken nuisance and order
him out of the bar.
Harold told his confidant, Brother Jack O'Leary, that one reason he left
Brooklyn in 1951 was "to get away from my in-laws." He didn't want his son exposed
to what went on at the bar, he explained. Rudy was at an impressionable age,
when one begins to observe and emulate. Harold wanted him far away from the
poisonous vicinity of Vincent's. He vowed that his boy would not end up like
Lewis, Leo's boy, who hung around the bar, around the numbers charts, and lived
with his family in the apartment above the new bar.
Sometime in the late '50s, Harold stopped tending bar full-time at Vincent's. On
January 12, 1959, two and half months shy of his fifty-first birthday and shortly
before Rudy's fifteenth, Harold Giuliani got an on-the-books, legit job. He was
hired for $3,300 per year as a grounds keeper for Lynbrook Public High School in
Lynbrook, Long Island, where Helen's younger brother Edward lived with his wife
Anna and their three children.
Perhaps in connection with that job, Harold requested information about the
cloud that had hung over him since 1934. A notation in the General Sessions
Court file indicates he sought copies of the" complaint and certification" of the
criminal case against Joseph Starrett. The notation lists Giuliani at his Garden
City address, indicating that copies of the key documents were sent to him there.
As a member of the buildings and grounds crew for the Lynbrook district,
Harold's day was spent maintaining sports equipment, buffing the terrazzo marble
floors, grooming athletic fields and, in the winter, salting parking lots and driveways.
Wearing his pants high over his hips, Harold would often tour the hallways
looking for gum, which he would scrape up with a putty knife stowed in his back
pocket. Michael Ortado, whose grandfather Bartolo Ortado worked with Harold
and used to bring young Michael to work with him on Saturdays, remembered
Harold as "huggy, very giving," adding, "just don't do something wrong. If you put
the can down in the wrong place, [Harold would say] 'It belongs over here.'"
During lunch, Harold and his fellow custodians would engage in apple-peeling
contests with their pen knives. Whoever could maintain the longest coil of peel
won. They would often argue which apples were better, Macintosh or Golden
Delicious, although, according to Ortado, Harold preferred tangerines. Often eating
a sardine sandwich, Harold would regale the guys with stories about the bar,
about the drunks who had poured their hearts out to him.
In October 1959, the Giulianis migrated once again. Harold, after only ten
months on the job at Lynbrook High School, took out a $162-per-month mortgage
on a new, comparably capacious split-level ranch house in North Bellmore, closer
to Lynbrook. Fixed in a tidy row of similar houses on a short block called Pine
Court, the Giuliani's new home, replete with a deck and a two-car garage, was
Harold's castle. The new house also had a bay window and a fa~ade of large cedar
shingles. Birches and silver maples lined the street out front, shimmering in the
fall breeze. Vine-covered trellises and cleanly cut hedges separated one yard from
another. The Giulianis had moved from a lower-middle class neighborhood to an
upper-middle-class town. Harold and Helen, always eager to conform, switched
their voter registrations back to the Democratic Party, because, in Helen's words,
"Bellmore was more of a Jewish area, and Democrats were more prevalent."
Helen had recently taken a job as a doctor's receptionist in Garden City, the
town from which she had just moved. Prior to this job, which she would only keep
for about a year and a half, Helen had stayed at home with Rudy, even though
Adelina was there. Helen had always wanted to be a teacher. Asthma, pneumonia,
pleurisy and a hoarse voice were the various reasons offered by relatives and
friends for her failure to realize that ambition. Over the prior fifteen years, her
only other job known to a half dozen relatives was a brief, part-time hitch at a
Brooklyn candle factory owned and run by the uncle of her sister Fanny's husband,
Sylvester Visconti. Part of National Candle's staff of about thirty people, including
her niece, Assunta, Helen had worked on the office side, typing up order
forms and filing expenses. "She typed beautifully," recalled Assunta.
Built in 1933, Bishop Loughlin Memorial High School is a beige brick monolith,
rising up from Clermont Avenue in Fort Greene, Brooklyn like a fourstory
monument to unnamed war heroes. Run by the De La Salle Christian
Brothers, it was the Exeter or Andover for working-class Catholic kids from
Brooklyn, Queens and Long Island. Through competitive entrance exams, each
parish from the two boroughs and the island selected its top two students to attend
the elite school tuition-free. In the '50s and '60s, Bishop Loughlin was a gateway
for the children of largely immigrant families to college and the middle class.
Life at Loughlin was firmly regimented, governed by a set of nonnegotiable
rules: Always wear a suit coat and necktie, but no loud ties and no loosening of ties
either; stand when your instructor enters the room; no ducktail haircuts; no
pegged pants; no smoking within two blocks of the school; no reading of newspapers
other than the New York Times; no lateness. The academic requirements were
rigorous, unforgiving. If a student failed more than two subjects, he was expelled.
There were forty-one teachers, all Christian Brothers attired in long black robes,
who moved from classroom to classroom throughout the day. Students remained
in the same room all day, except for lunch and gym, wedged into hard wooden
desks that were bolted to the floor. Every class commenced with the teacher reminding
his students "that we are in the holy presence of God." The bareness of
the classroom walls was interrupted only by a crucifix and an American flag. At
lunchtime, students would file down to the cafeteria, a basement room lined with
wall-to-wall lockers, and eat standing up at abdomen-high tables.
Freshmen at the prestigious school were continually, paradoxically, reminded to
humbly submit themselves to the will of Almighty God and also to strive for personal
excellence, to compete full-tilt against their peers in sports and academics.
Loughlin's wide corridors, walled with tiles, featured intimidating display cases
packed with trophies and congratulatory plaques. Displayed prominently was a
photo of the school's nationally renowned track team, which had appeared on the
cover of Life magazine in 1945.
When Rudy enrolled in 1957, the school's student population was 1,500, the average
class size, forty-five. The students were overwhelmingly Italian, Irish and
Polish. In Rudy's class of 378, there were only four black students and one
"I remember Rudy as a very personable young man," said Peter Bonventri, a
guidance counselor at Bishop Loughlin, who in Rudy's day, was the assistant principal.
"There was nothing absolutely outstanding about him, though .... He was
serious, but he enjoyed life."
Rudy would wake up before 6 A.M. every weekday morning and commute on the
LIRR with stockbrokers bound for Wall Street. He would get off at Atlantic
Avenue, walk eight blocks up a hill in Fort Greene and report for homeroom. His
relatives recall him as a hardworking student, never unwilling to do his homework.
Rudy himself would later state that one of his teachers had told his father that "my
grades were very good-I was one of the brightest kids in the class ... " That
teacher, Jack O'Leary, has a more accurate memory. "1 don't recall Rudy being on
the honor roll," said O'Leary. "1 would not think of him as in the top ten percent of
After seven semesters at Bishop Loughlin, Rudy's grade average of 84.8 earned
him a ranking of 130, putting him in the class's second quintile. His report cards
for those years show columns of mostly B's and Cs, a few Ns and one D. He scored
a 65 in chemistry, a 74 in Latin and a 92 in American history. His combined
College Board scores, 569 in verbal and 504 in math, were twenty-seven points
shy of 1100, and quite ordinary.
Mr. Giuliani, as his teachers called him, might have been one of those extracurricular
activities junkies whose attention was dispersed in too many directions.
During his freshman year, Rudy, just thirteen years old, was chosen as
homeroom president. He also signed up that year for the baseball team, afterschool
intramurals and the LaSalle Club, which raised money for students who
desired to become Christian Brothers. He had the top batting average on the intramural
team his sophomore year. Junior year, he joined the weightlifting team
and prom committee and founded an opera appreciation club. His activities accumulating
each year, he was appointed senior year to the sixty-member student
council. That year he also joined the catechism club, spurred by what he claims
was an interest in becoming a priest, and visited schools in poor neighborhoods to
give religious instruction. In a role he would later boast about in a major speech
Rudy was given a badge and anointed as a hall monitor in his senior year, super-
vising students standing on line for the cafeteria and handing out student court
summonses to misbehavers. In his first taste of electoral politics, Rudy was the
round-the-clock campaign manager for classmate George Schneider in his run
for senior class president. In his yearbook, the '61 Loughlinite, Rudy's mug
shows a serious, slightly chubby and eerily inscrutable young man.
Uncle Leo's gregarious son Lewis was a junior during Rudy's freshman year.
But, since Harold had urged Rudy to avoid his older cousin, the two had little, if
any, contact. Rather, Rudy began to assemble a coterie of loyal pals who shared his
sense of morality and righteousness. Alan Placa, now a Catholic priest on Long
Island, and Peter Powers, who would become Rudy's deputy mayor, were his two
closest buddies. He spent hours with both in their parents' living rooms, discussing
philosophy, religion and politics, sometimes until five in the morning.
Placa and Powers were early recruits to Rudy's opera club. The boys lured other
members by inviting them to performances at the Metropolitan Opera in
Manhattan and at the Brooklyn Academy of Music right down the street. For only
$1.50, they were allowed to stand in the balcony. The club members went to see
Verdi's La Traviata and Giacomo Puccini's La Boheme and Turandot.
The young opera aficionado was torn, he would later claim, between entering
the religious life and becoming a doctor. Through all four years of high school, he
vacillated between the two altruistic career options. He visited several prospective
seminaries, including the Diocesan, Jesuit and Franciscan. Senior year was when
his adolescent desire to become a priest allegedly hardened into adult intention. "I
decided very firmly that I wanted to go into seminary," Rudy later said. "I don't
remember what it was in the last year of high school that said to me, listen, I really
want to do this. I am gonna do it. I'm going into the seminary."
On an application form for a scholarship from Italian Charities of America, Inc.,
dated February I, 1961-the beginning of his second semester senior year-
Rudy's self-described passion for the priesthood, however, was nowhere evident.
After the question, "Why do you desire a higher education?" Rudy wrote: "To
study law or medicine."
(Italian Charities of America, Inc. eventually awarded the earnest young man a
$100 scholarship. The President of Italian Charities, to whom Rudy addressed his
cover letter, was Judge Anthony Livoti-the same judge who had discharged his
uncle Leo from Brooklyn Gambler's Court three years earlier.)
When asked in an unpublished 1988 interview if, while considering the priesthood,
he had ever chosen a favorite saint, Rudy, after a long pause and a laugh,
replied, "No. No, I don't think I did." But the former scholarship recipient had no
problems naming a favorite politician. When questioned about his "outlook on
life," it became quite clear that this young man was obsessed, not with the religious
oath nor the Hippocratic, but rather with a calling of a different color. "1 followed
the 1960 election very, very thoroughly," said Rudy. "1 used to travel on the
train, the Long Island Rail Road, and I can remember every morning getting two
or three newspapers and reading about the primary campaigns .... I can remember
the West Virginia primary, the questioning of [Hubert] Humphrey's war
record, and that was the key, the key primary that Kennedy had to win, because
[of] the absence of a Catholic vote in West Virginia and the predominance of a
Protestant vote, and if you could win that it would be a real test, that he could be
nominated as president. And I, I thought he was terrific. I thought Jack Kennedy
During his senior year, Rudy convinced a few friends to skip class and sneak out
of school to see JFK speak at a rally in the Garment district. The young fan shouldered
his way to the front of the crowd so he could shake Jack Kennedy's hand.
That fall, Loughlin held mock political conventions, and Rudy gave the nominating
speech for Kennedy.
The Kennedy-Nixon debates were what motivated the Loughlin students to create
their own electoral contest between the Purple, Gold and White parties. In the
days preceding the school election, Rudy campaigned vociferously as the official
manager and spokesman for White Party candidate George Schneider. The two drove
around together in a station wagon with a hand-scrawled sign affixed to the back exhorting
fellow students to "Jump on the White Wagon!" As the car coasted by the
school grounds, Rudy pumped his fist out the window, shouting Schneider's name.
A few days later, all three candidates, Schneider, Anthony Shanley of the Gold
Party and Joe Centrella of the Purple Party, gathered together on the stage of the
school auditorium to give speeches. After the speeches, hands went up with questions
for the nervous, neatly attired candidates sweating in their wool sports jackets.
In the back a student called out: "A question for Mr. Shanley."
Rising from a squeaky wooden seat, he asked Shanley why he had attacked his
opponents with the claim that they were too busy with extracurricular activities to
be senior class president. Wasn't Shanley himself busy with his own extracurricular
activities, such as theater?
Shanley peered into the audience to see that his questioner was none other than
his opponent's campaign manager, Rudy Giuliani. "1 said to myself, 'Hey this is
the other guy's mouthpiece,''' Shanley told the Daily News's Paul Schwartzman
years later. "1 was had. He put me on the spot." In the '61 Loughlinite, while other
students earned designations such as "Most Handsome" and "Most Popular,"
Rudy was awarded the distinction of being "Class Politician."
The class politician had, by his own estimation, maybe a half dozen dates in all
of high school. "I had two or three crushes," Rudy admitted. "But [it was] really
kind of retarded, certainly by modern standards."
When Jack O'Leary got a phone call at home one evening in the early.
spring of 1960 from one of his students' parents, he thought nothing of
it. Harold A. Giuliani frequently phoned the twenty-five- year-old Christian
Brother for progress reports on his son Rudy, who was known to act up in
O'Leary's homeroom at Loughlin. Sometimes, though, the coarse but courteous
man, who was more than twice O'Leary's age, wanted to talk about other things,
to seek counsel on matters in his own life.
This time Harold was calling about Rudy's cousin, Lewis Vincent D' Avanzo,
who, although better behaved than Rudy, had not been a typical student at the
somber Brooklyn boys' school. Plump, garrulous and jocular, Lewis would amble
through the halls, showily thumbing through wads of cash, slapping other students
on the back, extending his hand with bravado for his teachers to shake.
Harold asked O'Leary, then known as Brother Kevin, if it was okay if he came
by the Brothers' House with Lewis's father, Leo D' Avanzo, to talk.
"What's wrong?" O'Leary asked.
"Lewis is in trouble," Harold Giuliani said.
O'Leary knew very little about Harold's brother-in-law Leo. But Harold was his
friend, and O'Leary was not the kind of man to refuse a favor to a friend.
The three men met in the parlor of the Brothers' House, a large, spare room
with chairs lining the walls and a wooden table in the center. On the wall hung
stern portraits of Brooklyn bishops. O'Leary, a soft-spoken, prematurely balding
man with a kindly smile framed by deep parentheses, shut and locked the door
and then invited Harold and his anxious brother-in-law to sit down.
Stooped with humility, Harold Giuliani smiled and immediately lowered
himself into one of the chairs O'Leary had arranged around the table. But Leo
would not sit down. Shrouded in a camel hair coat with the collar turned up,
wearing a fedora with both front and back brims turned down, forty-eightyear-
old Leo D' Avanzo paced to and fro as his brother-in-law relayed his son's
After dropping out of St. John's University, Harold explained, Lewis signed up
with the draft board to go Vietnam, but was rejected because of obesity (at his
portliest, Lewis reportedly weighed well over 300 pounds). Looking for action, the
restless young man decided to steal a car parked on a street in Brooklyn, said
Harold. He then sold it to the first person he saw, a woman who happened to live
on that very street. He had also stolen some New York State Department of Motor
Vehicles license-making equipment out of a warehouse in Suffolk County, Harold
said. Now the eighteen- year-old was facing grand larceny changes, his fate at the
mercy of the unforgiving criminal justice system.
Striding about the room, Leo interjected that the cops had tortured his son.
They had tried to extract a confession, he alleged, by plucking pubic hairs out of
Embarrassed by Leo's remark, Harold quickly asked O'Leary if he wouldn't
mind speaking to the judge on Lewis's behalf.
Jack O'Leary took a minute to consider this. He had only known Lewis as
Rudy's cousin and Harold's nephew. But Lewis was, after all, just a kid-in fact,
only six years younger than O'Leary himself. And looking at the boy's father-a
tall, lean man whose ominous bearing made the Catholic brother uncomfortable-
O'Leary decided that Lewis probably wasn't to blame. And, again, he reminded
himself, it was his friend Harold Giuliani who was asking the favor.
So Jack O'Leary agreed.
In few days, O'Leary sat down in the judge's spacious Brooklyn chambers. But
before he could say anything, the judge, a diminutive Irishman dwarfed by his
ample desk, pre-empted his appeal. "Don't bother telling me, Brother," the judge
said. "I know what you're going to say. You're going to say Lewis was a good boy,
and he did well in school, and he was good to his teachers and so on."
The judge then described Lewis's father as a "petty mafioso" whose main criminal
venture was loan-sharking. As for Lewis-"I know how he grew up," the
judge said. "He hardly had a chance."
So the judge promised O'Leary that he would suspend Lewis's sentence. Then
he asked the young Christian Brother not to tell Harold Giuliani and Leo
D' Avanzo, who were both standing out in the hall, what he had agreed to do, "because
it would look like I was acting under undue influence," O'Leary recalls the
A day after Lewis's trial, Harold Giuliani phoned O'Leary to thank him.
"You did it!" Harold said excitedly. "You did it!"
O'Leary, keeping his promise to the judge, laughed nervously. Then he modestly
demurred: "Oh, right. I didn't do anything."
The staff at Loughlin were strict and exacting, but most of them also cared
about these boys and were devoted to their education. Some brothers had been or
would go on to become missionaries in third world countries as well as human
rights activists. Brother Jack O'Leary, who would work as a missionary in Kenya
after leaving Loughlin in 1963, was a deeply conscientious man whose belief in a
thorough education even got him into trouble a couple of times. Bound by the
strict Catholic curriculum, O'Leary taught the sanctioned English syllabus, which
included Shakespeare and classic texts such as George Eliot's Silas Marner.
Occasionally, though, he would weave, if only peripherally, other books into his
class, books outside the Catholic canon. He once mentioned The Catcher in the
Rye because J. D. Salinger's name kept popping up on the State Regents exam.
That night one of his students' parents called, irate. "Boy, did I get in trouble for
that," O'Leary recalled with a laugh. The ambitious teacher also organized a
school-wide book fair, at which students could buy steeply discounted paperbacks
like Lust for Life, Irving Stone's popular biography of Vincent van Gogh. Solely
because that one title contained the word "lust," O'Leary was later rebuked by a
senior brother, who publicly accused him during a staff meeting of leading the students
Although open-minded and mild-mannered, Jack O'Leary was no softie when it
came to discipline. When Rudy made a wisecrack in the middle of an afternoon
lecture, his homeroom teacher marched over to the lisping upstart and cuffed him
on the side of the head. In October 1959, the beginning of Rudy's junior year, at a
Bishop Loughlin open house, O'Leary was surprised when Harold and Helen
Giuliani tentatively approached him and thanked him for smacking their irreverent
son. "They asked me if I remembered the time I punished Rudy. I said yes.
They said, 'We want to thank you, because he became a much better student after
From that encounter, a relationship blossomed. Since Rudy and his friend Alan
Placa were, in their earlier years, misbehaving to the detriment of other students,
O'Leary "would report to my father on my conduct every week," Rudy said. This
weekly check-in system soon evolved into a friendship with the Giuliani family.
The young Christian Brother would join Rudy, his parents and his grandmother
for spaghetti dinners at their split-level in North Bellmore. "There wasn't much
furniture on the main floor," O'Leary recalled. "I think much of their resources
had gone into buying the house. It was a nice house in a nice neighborhood."
With O'Leary, Rudy finally had an opera listening partner. Many nights after
dinner, the two would retire to the basement and listen to Rudy's records, discussing
their agreed-upon favorites, such as Verdi's Otel/o. It was O'Leary who
helped Rudy found his opera club and served as its advisor. He also instilled in his
emerging erudite pupil an appreciation for Shakespeare and poetry. The devoted,
twenty-five-year-old Christian Brother would become one of the most important
influences in Rudy's early life. "He was terrific," Rudy said. "He spent a lot of time
with me, developing interests that I had that I wasn't comfortable about. Like
reading and opera, things that I wouldn't talk to my friends about, because they
would think I was a sissy."
Some evenings after dinner at the Giulianis, Harold, O'Leary and Rudy would
excuse themselves and take a stroll in a nearby park. They would discuss news,
politics, matters of religion. Rudy might prattle on about Jack Kennedy or jaw
with his father and teacher about the Yankees. Sometimes the high school senior
would tread a few paces ahead or lag a few paces behind, and when he was out of
earshot, Harold might breach other, more serious, matters with O'Leary. In the
spring of 1960, during one of these walks, while Rudy tagged behind them, Harold
made a sudden, cryptic confession to his confidant.
"I've done things in the past that I've paid for," Rudy's father said.
The men continued walking, wordlessly, the sounds of their feet on the path
suddenly loud in the wake of Harold's comment. Keeping silent, O'Leary waited.
He would let Harold offer an explanation, pour his heart out if needed. And
O'Leary was ready for whatever this hard, vexed man had to tell him.
But Harold Giuliani said nothing more. As dusk fell, Harold shunted the conversation
back to generalities, and Rudy caught up with them and the three sauntered
together through the dark back to the house.
The following winter, Harold Giuliani received a letter from Richard P. McLean,
the assistant superintendent of the Lynbrook Public Schools. Dated December 7,
1961, the letter read:
"We have heard no word from you concerning your return to work in the
Lynbrook Public Schools. The custodial staff is presently shorthanded one man.
May I ask that we resolve this issue as soon as possible .... Your immediate response
to this letter will be appreciated."
McLean was writing Harold because he hadn't been to work in months. Nearly
two weeks after the first letter, the assistant superintendent sent the fifty-threeyear-
old AWOL custodian a second letter:
"As yet I have received no response to my letter of December 7th. As explained
in that letter our custodian staff is shorthanded one laborer.
"Please accept this as official notification of the termination of your employment
in the Lynbrook Public Schools.
"May we take this opportunity to wish you good luck in the future."
Harold lost his job just as Rudy was finishing up his first semester at
Manhattan College. Asked a few months earlier-in his February 1961 application
for a scholarship from Italian American Charities-what he planned to do in the
case that financial assistance was not granted, Rudy had written: "My father will,
of course, help to pay towards my college education as much as he can. Then I expect
to work this summer. However, this will not be enough. I must, of necessity,
have some outside aid in order to complete my education." He had listed his father's
job as a custodian.
With scorching ulcers and the beginnings of a heart problem, Harold Giuliani
was no longer the swaggering, hearty man readily disposed to put the knuckles on
someone for looking at his wife the wrong way. But the reason he had failed to report
to work since the previous spring was not a physical one. "Harold had something
of a nervous breakdown," explained his confidant Jack O'Leary. "He wasn't
working at the time."
Harold told friends that one of the events that triggered his breakdown was an
incident in a Long Island state park in the spring of 1961. For the first time in
many years, he was arrested-a chilling, jolting experience that abruptly exhumed
old memories. The offense was trivial but embarrassing. Harold had long suffered
from severe constipation. One afternoon, while strolling in the park, he suddenly
felt the need to go. When he found a public rest room, he pulled his pants down
and began doing deep knee bends outside the stalls to expedite the process. A police
officer happened to walk in right then. Harold was arrested for "loitering" and
hauled down to the local police station. The charges were eventually dismissed,
but the experience haunted the fifty-three-year-old.
"The last time I saw Harold," recalled O'Leary, "he was practically bed-ridden.
He was sitting out on a lawn chair in the backyard all pale and terrible-looking."