Chapter 6 - Ethical Culture Fieldston School

“Mr. Sinatra Gets Rejected”
Not much came of Marty O’Brien’s boxing career. Still, the O’Brien name
continued to have its uses, particularly when wielded by his bride, the Genoan‐
born Natalie “Dolly” Garavante, who apparently did most of the family’s
thinking. It was she who, as a major backstage player for the Democratic party in
Hoboken, orchestrated Marty’s appointment as a city fireman. It was she who,
after borrowing money from her mother, opened a saloon she named “Marty
O’Brien’s” (this during Prohibition). And it was she who, when her only child
was born in December of 1915, made sure he had an Irish godfather, Frank
Garrick, to someday get him a job for The Jersey Observer. Garrick got him hired
to bundle papers, but when young Francis was fired for posing as a sportswriter,
Dolly never forgave Garrick for failing to get the paper to take him back.
You get the idea: Francis owes a lot of what he became to Dolly. Part of
this is sheer economic privilege. Later in life Sinatra would emphasize the gritty
urban milieu of his youth, but without underestimating the insularity and
widespread poverty that surrounded him, it must nevertheless be said that he
lived a life of relative affluence. In 1932, with the Depression at its height, the
Sinatras moved into a four‐story $13,400 house (a price tag of affluent
Westchester County proportions). Young Frank, an only child, had so many pairs
of pants that he had the nickname of “Slacksey O’Brien.” But the advantages in
life that Dolly gave Frankie were more than just material; they had more to do
with a sense of confidence that would lead a high school drop‐out to believe he
could pass himself off as a sportswriter, and to later make both his high school
and journalistic “experiences” fixtures of his official publicity biography. Here,
truly, was a child with great expectations.
Still, an ambitious mother will only get any child so far, particularly a
child who, much to that mother’s dismay, was indifferent about education and
American History for Cynical Beginners
7