s the patron of hundreds of poor public school students in three cities, George A. Weiss, a Hartford money manager, has had his share of heartbreak.

Mr. Weiss's first major venture into educational philanthropy, in which he promised 112 sixth graders from West Philadelphia that he would pay for college if they got in, yielded as many felons as four-year-college graduates (20 each). Since the program was announced, in 1987, five of the 112 have been murdered, and a sixth, with whom Mr. Weiss had grown particularly close, was killed riding in a stolen car that crashed. But Mr. Weiss has not given up. Over 17 years, he has tried again and again, starting four similar programs, each one revised to deal with the missteps of the past and expanded to anticipate newly apparent obstacles on the road to a high school diploma and beyond.

Now he is bringing his honed effort, on a larger scale than he has tried before, to perhaps the most politically fraught territory in the country's educational landscape: the New York City public schools. In September, 400 kindergartners from five Harlem elementary schools will be the next crop of students to benefit from Mr. Weiss's program, called Say Yes to Education. Mr. Weiss has pledged $20 million toward the cause and is trying to raise $30 million more.

About $20 million will pay the full costs of tuition at college or vocational school, if the students ultimately defy the odds by graduating from high school and earning acceptances. The rest will be spent well before, on extras that Mr. Weiss hopes will increase the likelihood that the children graduate from high school: a reading specialist and social worker for each selected school, extensive summer and after-school programs, even scholarships for the chosen children's parents, should they pursue their own education. Mr. Weiss's first inspiration was a community service project, in which his University of Pennsylvania fraternity held a Christmas party for a dozen sixth graders from South Philadelphia. Mr. Weiss became close with the group, and years later, he said, one of them told him over dinner that all 12 had graduated from high school because they would not have been able to look him in the eye if they had not.

At that point, Mr. Weiss, who started working as a restaurant busboy when he was 11 to help support his family, said, ''I just made a pledge with God: If you ever give me the financial wherewithal to make a difference, I would do something about education and have a high degree of caring and personal involvement.'' Over the years, things have sometimes become so personal that it has been difficult for Mr. Weiss to draw the line. He has been known to lend Say Yes children, particularly from the first group, money for rent and medical procedures. He installed an 800 number in his Hartford office so the students could call for personal advice, financial help or just to say hello, which they often do.

More than once, he has urged drug dealers in his programs to go clean, but he has refused to abandon participants who go astray. He has visited his students in jail and has performed several tearful eulogies. ''A lot of people are still acting like he owes us something when he gave us so much,'' said Shermika Brown, 29, a hairdresser, who was part of the first program and remains close to Mr. Weiss. In his New York corner office, overlooking Park Avenue, he keeps on the desk a photograph of Walter Brown, the student killed while riding in a stolen car. ''He got me in touch with my inner self, my emotional self,'' Mr. Weiss said. ''I cry a lot when I see these kids.''

Mr. Weiss's program is not a new model. It is loosely patterned after I Have a Dream, which a wealthy businessman, Eugene Lang, started in New York City more than two decades ago. But Say Yes to Education is more costly and extensive. So far, Mr. Weiss has spent $33.4 million on 368 children. It is also a marked departure from many of the other major philanthropic projects in the school system under Mayor Michael R. Bloomberg, in which large chunks of money have gone toward centralized projects with the potential to influence tens of thousands of students, like the creation of new small schools and a $75 million academy to train principals.

''For people who are interested in showing whole system change, this is much less sexy, but it's so much more important,'' said Randi Weingarten, president of the United Federation of Teachers. ''This is about the nitty-gritty work of helping individual kids.'' As Mr. Weiss has learned, that work can seem limitless. Each successive Say Yes to Education program has been a sobering lesson in the breadth, depth and complexity of the obstacles standing between children from poor neighborhoods and high school diplomas.

''It kind of sounded like it should be a sure thing, you dangle a college carrot in front of these kids and they'll just go for it,'' said Marsha Mattison, who taught a group of third graders in Cambridge, Mass., who were the beneficiaries of one of Mr. Weiss's earlier programs.

''When you saw that there were some children who were having tremendous obstacles in school with learning and some kids who were having tremendous obstacles at home with family problems, those kinds of things interfere with success.'' Mr. Weiss, however, sees all his ventures as successes. ''I look at it as, how do you put a dollar amount on kids that you love, and how do they become productive members of society?'' Mr. Weiss said. Mr. Weiss, 61, a towering man with gray hair and a cherubic face, says he is simply leveling the playing field for disadvantaged children.

He grew up in Brookline, Mass., the son of parents who fled Austria around World War II. They never had much money but taught him to value learning.

After college, he turned down an opportunity to go to Harvard Business School because he had to support his parents, he said. He took a job in Hartford as a stockbroker and, in 1978, started his own money-management business. George Weiss Associates now has more than 100 employees, manages more than $1 billion and has offices in Hartford and New York. Mr. Weiss helped raise two daughters, now grown, although his marriage to their mother eventually crumbled.

As an adult, he overcame serious back problems to become a fourth-degree black belt in two martial arts. He is a lifetime trustee of the University of Pennsylvania, which he has given about $45 million, and is chairman of its undergraduate financial aid committee.

Nothing seems to inspire him as much as Say Yes to Education's shining stars, like Harold T. Shields Jr., 29, who graduated from Penn, is now studying for a masters in social work and started his own scholarship fund by putting down $10,000, and Jarmaine Ollivierre, 28, an aeronautical engineer who graduated from Tuskegee University with degrees in aerospace engineering and physics.

''I wouldn't be where I am today without it,'' Mr. Ollivierre, 28, said of the program. The first program resulted in much higher high school graduation rates than usual for the West Philadelphia neighborhood, even though the selected school had an overwhelming number of special education students. More than half the female participants were pregnant by age 18. For the next programs -- one in Philadelphia, where other philanthropists paid for the scholarships, and another in Hartford -- the schools were more carefully selected and the children were younger. In New York, Harlem was chosen because it has high dropout rates and is near Teachers College at Columbia University, which will be deeply involved in the program.

In the meantime, Mr. Weiss is trying to raise $30 million and has had dozens of meetings with public officials. He said he was thrilled to come to New York City, despite some friends' advice that he steer clear of its rough-and-tumble political maneuvering.

Perhaps thinking only of Mr. Weiss's philanthropic ventures, and not the business savvy that earned him millions in the first place, they warned him that New York City politics were too rough for such a well-intentioned man.