First of two articles On his first day at Harvard Law School, a moon-faced dynamo named Howard Milstein fell for a smart, soft-spoken redhead named Abby Sniderman. So he asked her out. But that's not all he did. He also drew up a schedule, titled "Where Is Abby Today?," so he could walk her to and from all her classes. He began carrying her favorite snacks -- pistachio nuts and peanut butter cups -- in his pockets at all times, in case she wanted one. He started scurrying to campus from his Boston penthouse every morning to eat powdered eggs with her at the dining hall, elbowing aside her other suitors. Eventually, he persuaded her to marry him. The message is that when Howard Milstein wants something, he is relentless about getting it. It was true when he vowed to graduate summa cum laude from Cornell University, becoming the university's first economics major ever to do so. It was true as he built one of Manhattan's towering real estate empires, so infuriating competitors that he felt compelled to hire bodyguards. And it was true when he challenged Time Warner Inc.'s cable-TV monopoly in New York, often wiring buildings for his own cable service without applying for the appropriate licenses, enraging regulators from Albany to Washington and incurring more than $1 million in fines. It was equally true when he decided last year that he wanted to own a professional football team. After the 47-year-old billionaire developer lost his bid for the Cleveland Browns last summer, he vowed he would not let that happen with the Washington Redskins. Now he and two limited partners -- his younger brother, Edward Milstein, and Bethesda businessman Daniel Snyder -- are attempting to buy the team and stadium for $800 million, the most ever paid for a U.S. sports franchise. The National Football League is reviewing the sale, openly unhappy that Milstein, rather than John Kent Cooke, is the buyer. But Milstein's allies and enemies alike warn that he rarely takes no for an answer. "When Howie wants something, he doesn't stop until he gets it," said Congressional Institute senior fellow Helen Kanovsky, a longtime friend who introduced Milstein to his future wife. "He's not the kind of guy who backs down." In the rare cases when Milstein doesn't get his way, he gets mad -- and then he tries to get even, often through litigation. He and his major partner in the New York Islanders pro hockey team fought hard to secure taxpayer money for a new arena, but when they failed Milstein broke off negotiations and filed suit to break the team's lease. He is suing Time Warner for $1 billion over the cable wars, and soon after he sold most of his cable firm, he sued his new partner. He vigorously battled one of his longtime employees in court over an age discrimination suit that the employee's attorney said could have been settled with $10,000 in severance pay. There is no doubt that Milstein's aggressive style has paid dividends for him. He now is the primary figure in a third-generation real estate empire said to be worth $5 billion. It includes thousands of swank Manhattan apartments, some of them on the market for as much as $12 million; some of the city's choicest office space, including the Bank of America and Guardian Life Insurance buildings; and valuable undeveloped land throughout the city. The family also owns the Ramada Milford Plaza and other New York hotels, as well as the cash-rich Emigrant Bancorp Inc. savings bank. In addition to his stake in the Islanders, Milstein is the leading investor in a West Coast computer firm, PeerLogic, Inc., as well as a new journalism magazine, Brill's Content. Milstein is not particularly ostentatious for a billionaire, but he certainly enjoys the fruits of his family's success. He lives in a Park Avenue apartment and owns homes in Mamaroneck and Southampton as well, with the requisite butlers, maids, swimming pools, boat docks and tennis courts. He also gives millions of dollars and a substantial portion of his time to causes ranging from Lincoln Center to Cornell to the New York Blood Center. Along the way, though, Milstein has made his share of enemies. Many of them refused to be quoted by name, saying it is virtually impossible to do business in New York without running into the family's interests. Milstein also declined comment because he does not want to make public statements while the NFL is weighing his bid. While Milstein is widely admired for brains and ability, he also is well-known for his headstrong attitude and his willingness to turn to the courts. "He keeps a lot of us busy," said a lawyer who has worked for him. "I wouldn't want to make him angry. He's a 400-pound gorilla." The bottom line is that behind Milstein's cherubic, boy-next-door face and gleeful belly laughs lies an extremely tough guy. His allies say that's simply what it takes to thrive in an industry as important to New York as politics is to Washington, an industry dominated by titanic personalities such as Mort Zuckerman, Leona Helmsley and Donald Trump. "He's arrogant and difficult," a former business associate said. "If you work with him, you have to understand: there's only one way and it's Howard's way." But Milstein can play rough outside the real estate arena, too. A few year ago, a jogger jostled Abby Milstein while she was walking with Howard and his friend Doug Diamond around the Reservoir in Central Park. Milstein chased the man down, jumped him from behind, pinned him to the ground and forced him to apologize. And according to Diamond, the man was a lot bigger than Milstein. "Typical Howard," Diamond recalled with a chuckle. "He's a tough guy." Milstein's third-floor work space on Madison Avenue is decidedly nondescript. According to those who have visited, he shares an 18th-century British partners desk with his younger brother, Edward, his clearly subservient minor partner in the Islanders and Redskins ventures. He serves as a mentor of sorts to Eddie, who chose the family business over college years ago. The office has one other eye-catching feature: a huge, sepia-toned reproduction of a Gustave Caillebotte painting of three men on their hands and knees, scraping wood floors. It hangs right where Howard can see it from his desk, and that is no coincidence. Milstein likes the constant reminder of his Russian immigrant grandfather, who started in this country on his hands and knees, scraping and refinishing floors, always dreaming of a better life. From those beginnings, Morris Milstein founded Circle Floor Co., which won federal contracts to install wood floors for Army barracks during the 1940s. After World War II, the firm began making floor tile for Sears, Roebuck and Co. and other home centers, ultimately grabbing much of New York's commercial flooring market and venturing into construction. The men who really set the standard for Milstein were his father, Paul, 77, and his uncle, Seymour, 79, two uncompromising figures who became power brokers before he was born and are still active in the family business today. The elder Milsteins expanded the family's construction enterprises and they are considered two of the toughest businessmen around. In his authoritative biography of public works builder extraordinaire Robert Moses, author Robert Caro described how Seymour took advantage of a Moses slum clearance project to buy $15 million worth of real estate for $1 million, cash out, then join the payroll as a consultant. Paul summed up their philosophy 20 years ago in a New York Times interview: "We live in a jungle. In order to survive in a jungle, I guess you've got to be tougher to be a winner. My competitors, my adversaries and my friends cannot really say I'm tough. They don't understand the word tough." Milstein summered in Europe with his family as a boy, attended the Metropolitan Opera in his family's private box and flew home from his college graduation in his family's private jet. But he likes to say he was raised with "middle-class values," steeped in the importance of education, hard work, charity and family ties. The Milsteins, after all, were rich, but not showy rich. They've given more than $50 million in gifts to Columbia Presbyterian Hospital, which named a wing after them. They sent Howard to public high school in Scarsdale. If Milstein still acts a bit like the smartest boy in the class, the one who has all the answers and isn't shy about saying so, that may be because he always was. He was a brilliant student, a star of the debating team, the proud recipient of a Daughters of the American Revolution prize for good citizenship. When he was about to switch schools in junior high and found out that his new classmates already had taken Spanish, he had his mother teach him the language that summer so he could start school knowing more than anyone else. "Howard's always been like that," said Diamond, a Manhattan marketing executive who has partnered with his old friend on ventures to sell a new brand of Polish vodka and launch an International Boxing Hall of Fame in Las Vegas. Milstein entered Cornell in the '60s and moved into the college's first coed dorm, but he was never a '60s kind of guy. He tooled around campus in a white GTO. He rowed crew and played tennis. He took advanced classes in his freshman year, studying intellectual history and philosophy, opera and architecture. After his older sister, Roslyn, graduated summa cum laude from Yale University, he told his friends he would have to do the same at Cornell, and he did. Even in college, he had a take-charge attitude. Mike Hodin, who lived with Diamond and Milstein at Cornell, remembers Milstein as the leader of the threesome even in deciding who did the chores. Milstein wrote up index cards dividing up duties for cooking, cleaning and shopping, even who would make the salad at dinner. And what were Milstein's duties? "Well . . . mostly, he supervised," Hodin said with a laugh. After graduation, Milstein returned to New York to work for his family, starting as an executive on a new 5,800-apartment Coney Island project, Starrett City. It was his first exposure to excavation contracts and commercial lease negotiations, and he soon decided he needed to learn more about law. After receiving a perfect score on his law boards, he went off to Harvard Law School, where he adapted quickly to the cutthroat competition immortalized by the 1973 movie "The Paper Chase." He spoke up so often and so forthrightly in his contracts class that his professor, Clark Byse -- the legendary model for the intimidating professor in the film -- began referring to students who agreed with Howard as "Milsteinians." The Socratic method, Milstein used to tell his friends, was nothing compared with dinner at the Milstein household. Today, Milstein's household includes Abby and their son, Michael, 9. Howard still vacations each year in Puerto Rico with his extended family of parents, siblings, nieces and nephews. He walks his son to school every day. He is a voracious reader, tennis player and golfer. He has breakfast once a month with his college roommates, Hodin and Diamond. He also meets once a month in his office with a dozen other executives to discuss the Torah with Rabbi Burt Visotzky, a professor at the Jewish Theological Seminary. And he doesn't always take himself seriously; at a recent business meeting in Munich for PeerLogic, he suddenly began singing "Ode to Joy" in German. But unlike former Redskins owner Jack Kent Cooke, Milstein confines his unpredictable behavior to the business world. His personal life does not show up in the gossip columns. Throughout his career, Milstein has made lemonade out of seemingly rotten lemons. For example, his fellow developers snickered when he launched the Milford Plaza two decades ago in a then-declining neighborhood near Times Square and affixed a plaque dedicating the hotel to the future of then-declining city of New York. Now the neighborhood is revitalized, the city is booming and the hotel is at 96 percent occupancy. He certainly fights hard. The question is, does he fight fair? "Look, I think the world of the guy, but I know he's a tough businessman," said former New York Mets first baseman and announcer Rusty Staub, who became friends with Milstein through charity work and their membership in the Confrerie des Chevaliers wine club. "I'm sure if you were sitting across from him doing a business deal, you might feel differently about him." Perhaps the starkest example of Milstein's no-holds-barred style was his challenge to Time Warner Cable's hold on local cable television in the late 1980s, a battle he fought with the same ardor that characterized his pursuit of his future wife. Milstein founded Liberty Cable Corp. after arguing with Time Warner over the cost of wiring the Milford Plaza, and his upstart company soon became well known through tiny ads at the bottom of the front page of the New York Times announcing that specific buildings had been "liberated from the cable monopoly." But during his ownership, he ran afoul of the New York state cable commission, the Federal Communications Commission and the Motion Picture Association of America for wiring buildings illegally, misleading government agencies in filings and underpaying royalty fees. "Liberty's overt actions in this matter, coupled with its lack of candor about important underlying facts, manifest a disrespect for this regulatory agency, the Federal Communications Commission, the judiciary and the law itself -- a disrespect of a kind which this Commission, frankly, has never previously encountered," the state commission wrote in November 1995. A month later, the commission attacked Liberty again for continuing to violate its orders, calling the company "an incorrigible telecommunications scofflaw" and imposing a $1,000-a-day forfeiture order. Ultimately, Liberty paid a $60,000 forfeiture to the commission and agreed to pay a $1 million forfeiture to the FCC. To make matters worse, an FCC administrative law judge rejected that punishment last year as insufficient, saying the licenses Liberty had applied for should be denied. That decision currently is being appealed. But the administrative judge concluded that three-fourths of Liberty's buildings were wired illegally and that service to many of them had been initiated before Liberty had even filed applications to the FCC. He also said that Liberty officials "lacked candor" and that they had "consistently been misleading . . . and deliberately dilatory." Milstein has called Liberty Cable one of his greatest and most innovative successes, and he has said that the problems with the agencies were merely bureaucratic stumbles blown out of proportion by Time Warner's regulatory allies. Lloyd Constantine, his attorney in the case, said the whole battle arose out of misunderstandings, and he noted that many of the rules Liberty was accused of violating were later changed to reflect advances in technology. "It was all done through confusion and inadvertence," Constantine said. Milstein's other venture into the sports world has led him into criticism and litigation as well. Last February, he and a partner bought the woeful Islanders for $195 million and vowed to bring a Stanley Cup to Long Island. But they spent most of the past year battling with local politicians to develop the land around Nassau Coliseum, and Nassau County's top official called them "pigs at the trough" during a dispute over public subsidies for a new arena. The partners then sued the Coliseum's managers over safety concerns that many observers found dubious and they tried to cancel the team's home exhibition season. A judge ordered the team to return to the Coliseum, where it now is having one of the worst seasons ever. And many fans who had expected Milstein and his partner to revive the team now blame them for refusing to spend money on high-priced free agents. But Milstein's many friends, who range from former Mets star Staub to former opera singer Beverly Sills, and loyal allies, who include New York Attorney General Elliot Spitzer and former New York deputy mayor John Zuccotti, say he has been unfairly blamed for the plight of the Islanders and for his various scraps with competitors. They say he is a brilliant, fun-loving guy who wants to make a name for himself in a family of giants. They say he also has the courage to stand up for his principles. The best example, they say, is his effort to turn around Douglas Elliman, a huge realty brokerage and management firm that had fallen on hard times before Milstein bought it in 1989. Milstein soon found out that at a party thrown by a plumbing contractor, about $56,000 in cash was distributed to 20 apartment managers. Milstein decided to launch an investigation of the company he had just bought, hiring Corporate Loss Prevention, a corporate detective agency, and Richard Aborn, a former assistant district attorney. The investigators found massive fraud and payoffs from roofers, plumbers and interior construction contractors who were inflating their prices and then paying kickbacks of 10 percent to building managers. Aborn attributed Milstein's motives to a true sense of public duty, as well as the obvious fact that fraud was inflating his prices. For whatever reason, Milstein took the information straight to New York District Attorney Robert M. Morgenthau, whose office launched a probe that resulted in the convictions or guilty pleas of 94 people throughout the industry. Milstein received death threats, and he used bodyguards for two years. One of them is now his driver. "It did not make him a popular man within the industry," said Dan Castleman, chief of investigations in Morgenthau's office.

Now, some acquaintances believe Howard is trying to out-tough his father and be seen as the Milstein to lead a new generation, to prove that even if he hadn't been born with money, he would have been smart enough and tough enough to make it himself. "He is a tough-minded, aggressive businessman. He's fair, but he is ambitious and wants to make his mark in the world," former deputy mayor Zuccotti said. "He's from an enormously successful family. He wants to earn it himself. What drives him is his plain, ordinary ambition." But ambition does not quite explain his vigorous work for charitable and civic causes, which he has told city officials he plans to extend to the District if he gets the Redskins. Howard is particularly devoted to Cornell, where he is a member of the board of trustees, an overseer of the medical college and the chairman of the investment committee, which handles the school's $3 billion endowment. He helped found the school's real estate program, and taught a popular course in real estate development as a visiting professor one year. Charity may be a family tradition, but Milstein's friends say his feelings of duty to others are especially strong, in part because he has stared death in the face. He was diagnosed a decade ago with a malignant melanoma, and while he is cancer-free now, he still covers himself from head to toe when he is under the sun. Once, while traveling in Europe, he went into anaphylactic shock from an allergy to shellfish. And last year he was hit by a sport-utility vehicle while jaywalking across Madison Avenue. He walked home. "He's an extremely strong individual -- physically, mentally and emotionally," attorney Constantine said. "On some level {those events} made him fearless." How fearless? When he sold off Elliman's management division, he was invited to speak at a black-tie dinner celebrating the closing of the deal. He accepted. But he also decided to write wry new lyrics to not one, not two, but three familiar standbys: "You're the Top," "Don't Cry for Me, Argentina" and "La Donna Mobile." One stanza went: "You bought our company/Too bad it wasn't free/It's running blissfully/Even without me." And since he had never performed in public before, he hired Duke Ellington's granddaughter to teach him a soft-shoe song-and-dance routine. Milstein sang for 15 minutes at dinner, startling the 100 guests with his booming tenor. And as he proudly told his friends, he was good. Tuesday: Partner's turnaround Staff writer Liz Leyden and staff researcher Richard Drezen contributed to this report. Milstein's Main Ventures Howard Milstein is involved in a slew of business ventures, including an effort to market a luxury brand of Polish vodka, the new journalism magazine Brill's Content and the upcoming International Boxing Hall of Fame in Las Vegas. Here are some of his most important: Douglas Elliman is New York's largest residential real estate brokerage. It sold $2 billion worth of property in 1998 -- more than 4,000 properties -- and rented 2,000 apartments. Howard Milstein is the chairman and chief executive. Emigrant Bancorp Inc./Emigrant Savings Bank: The thrift had 1997 assets of $6.1 billion and earnings of $94.5 million. It is New York's fourth largest savings bank and 90 percent of its loans are residential mortgages. Six of its 17 directors are named Milstein. Howard is co-chairman of the bank and co-chief executive of the holding company. Milstein Properties builds both residential and commercial properties in New York. Howard is a managing partner. He is also a managing partner of Milstein Ventures, the family's investment unit. Milford Hotel Corp. owns and operates several New York hotels, including the Ramada Milford Plaza. Howard is the chairman and chief executive. The New York Islanders are among the worst teams in the National Hockey League this season. Howard and his brother, Edward, own about 45 percent of the franchise. Miglin-Beitler Properties is the largest real estate management and leasing firm in Chicago. Howard bought 50 percent of the company last year. PeerLogic is a software development and systems integrations firm in San Francisco. Howard is the controlling investor and a member of the board of directors. Brill's Content is a new journalism magazine. Howard is its leading investor. CAPTION: Howard Milstein, center, with partners in the bid to buy the Redskins -- his brother, Edward, left, and Daniel Snyder. ec CAPTION: There is no doubt that Howard Milstein's aggressive style has paid dividends for him. In the rare cases when he doesn't get his way, he gets mad -- and then he tries to get even, often through litigation. ec