The painting, which captured Giuliani's trademark toothy grin and dimples, joins a collection of more than 100 portraits in the nearly 200-year-old City Hall. The portraits include U.S. presidents, New York governors and 44 other New York City mayors.
Giuliani, who served two terms from 1994 to 2001 and earned accolades for his handling of the city following the Sept. 11 terror attacks, was painted by Everett Raymond Kinstler, an artist commissioned to paint portraits of two U.S. Supreme Court justices, four secretaries of state and various other dignitaries and celebrities.
The piece was painted during several sittings — a few times in 2006, before Giuliani's failed bid for the Republican presidential nomination, and again this year.
At a ceremony attended by various Giuliani-era aides and commissioners, the former mayor said he dragged his feet on having the painting done because of a long-held fear. His wife, Judith Giuliani, ultimately persuaded him.
"I'm superstitious about portraits — they're for dead people," he said. "You unveiled the portrait, and I'm still here, so I guess the superstition doesn't work."
The likeness of the former mayor, whose hairline receded throughout his two terms in office, depicts him as he looks now.
In the painting, he is standing, leaning on a railing, wearing a red tie and an American flag pin on the lapel of his pinstriped suit, subtly evoking his favorite baseball team.
"I tried to persuade him to do the entire uniform, but he wouldn't do it," Giuliani joked. "He said it would be inappropriate."
Giuliani's successor, Mayor Michael Bloomberg, said having the portrait in City Hall will serve to remind everyone of his legacy.
"It really captures the pride and joy I think that Rudy felt when he was mayor," Bloomberg said.
In City Hall, even the portraits play politics.
When Giuliani took office, he had the portrait of his political hero, Republican Fiorello LaGuardia, moved from an out-of-the-way spot into a prominent position facing his desk.
And during Giuliani's second term, after a renovation of the Blue Room, he had the paintings of former Democratic mayors Ed Koch and David Dinkins — with whom he had strained relations — moved out and relegated to the hallway.
And that is where Giuliani's portrait will now hang.