Remembrances of 'Tookie': Despite world renown, Frank Dileo was still a small-town guy at heart

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As the record executive-cum-personal manager responsible for catapulting Michael Jackson to his career peak in the 1980s, Frank Dileo gained riches, traveled the world and met with presidents, princes and the otherwise famous.

But here, in his hometown, he will forever be known as "Tookie," the charismatic, friendly, driven Italian kid from Point Breeze, whose deep roots, big heart and outsized personality could never be altered by fame and fortune.

Mr. Dileo ascended from selling records out of his car trunk to the stratosphere of the entertainment industry, but he never forgot boyhood friends like Fat Pat, Skeeter, and Bobby the Rat, the zing of his sister Rosemarie Dileo's hot sausage or how Sundays are sacred for two reasons -- Mass and the Pittsburgh Steelers.

Mr. Dileo, 63, died Wednesday in North Lima, Ohio, from complications of triple-bypass surgery in March.

"He was a simple man," said his uncle, Michael Ciocca of Plum, who being only eight years older than Mr. Dileo grew up with him more as a brother. "He was small in stature but, man, he was a giant. He was a down-home guy, a lovable character but a great businessman.

"He had different personas but deep down, inside his heart, he was a Pittsburgh kid."

That Pittsburgh kid made quite a hit worldwide, first as associate director of promotion for Epic records, signing such stars as Cyndi Lauper and Culture Club. He worked with Mr. Jackson on the "Thriller" album and in the phenomenal wake of that album's success, Mr. Jackson asked him to be his manager.

At 5-foot-2 and more than 200 pounds, with a pony tail and an omnipresent gigantic cigar, Mr. Dileo and the rail-thin, Peter Pan-like Mr. Jackson made for quite a visually interesting couple. And a successful duo at that. They worked together on a movie, lucrative Pepsi commercials and two tours, including a solo one that became the largest grossing concert tour of all time. When that tour came to Pittsburgh, Mr. Dileo bought 1,500 tickets for family and friends.

Mr. Jackson fired him after five years, but Mr. Dileo supported Mr. Jackson in 2005 when he stood trial on child molestation charges. And in 2009, Mr. Jackson asked Mr. Dileo to manage his "This Is It" tour, but the singer died on June 25, 2009.

Before all of that, before he was married with a son, a daughter and a grandson, Mr. Dileo was the kid whose grandfather and father ran Dileo's Tavern in Homewood. In that popular hangout, the pizza was great and the hot sausage sandwiches "were almost world famous," said Mr. Ciocca, who began making pizza there at age 12.

Mr. Dileo would spend a lot of time at Mr. Ciocca's home in Larimer, and the two would enjoy the sights, sounds, smells and excitement of the 11/2-mile stretch of Italian heaven on Larimer Avenue -- filled with Italian bakeries, grocery stores, social clubs and characters galore.

"It was a great. Tookie loved it," Mr. Ciocca said.

Later in life, Mr. Dileo would play the character Tuddy Cicero in Martin Scorsese's Mafia drama "GoodFellas," set in an Italian neighborhood similar to Larimer Avenue. Ms. Dileo, of McCandless, said the character's name "Tuddy" was based on her brother's nickname, "Tookie," which was given to him by his maternal grandmother for reasons no one can now remember.

Mr. Dileo attended St. Bede's School where he played guard and nose guard in football. Despite his lack of stature, he won the most valuable player award, which was taller than he was, in an all-star game, his uncle recalled proudly.

After that, it was off to Central Catholic where Brother Benedict Oliver, now director of the school's writing center, remembered Mr. Dileo as someone who was highly respected and genuinely liked. He played nose guard and guard on the football team for four years and was a member of Student Council and the theater group.

On the night he opened playing mobster "Big Jake" in "Guys and Dolls," his father died of cancer at 41.

"You couldn't find a nicer, more pleasant person than Frank," Brother Oliver said. "I don't know anybody who didn't like him. He was gregarious, fun-loving but by the same token was serious when he needed to be serious, such as on the football field or in doing his schoolwork. He was a nice person to be around."

Mr. Dileo's success in the entertainment world, particularly as the personal manager of one the biggest recording and performing artists of all time, wasn't at all surprising to Brother Oliver.

"If he had been a success as an athlete or as a politician it wouldn't have surprised me either because of his personality, because of his abilities and stick-to-itiveness, because he was a person who pursued until the end something he was interested in.

"I could see that for Michael, who had problems, that Frank would be someone he could put his confidence in and knew his confidence would be well placed."

Attorney James DePasquale, who was two years behind Mr. Dileo at Central Catholic, recalled how they and a group of guys hung out in Oakland during high school and thereafter.

"He was always personable, a really nice guy, good for a lot of laughs. He was a character, is what he was, more than anything. He was a bon vivant type of guy.

"When he'd come into the crowd with the guys in Oakland he was the star of the show with nonstop stories, all of them funny. He always dominated the conversation. He'd be talking about all of those characters from Larimer Avenue, like 'Vince the Slob' or 'Joe the Blob.' I chuckled every time I saw Frank Dileo from the moment I laid eyes on him.

As for playing Tuddy Cicero in "GoodFellas," Mr. DePasquale said, "He was playing that character from the moment I first knew him to the last time I saw him. He was always telling stories, acting like that character.

"He was a tremendously likable human being," Mr. DePasquale said. "He just had charisma, which is different from being likable. It didn't surprise me at all when I heard he was involved with Michael Jackson.

"People wanted to be around him, he made you laugh, he was fun to be around and he treated people the right way, too."

While Mr. Dileo's success may have given him entree to some of the world's most important people, his sister said that always "when he talked to you, you were the most important person on Earth."

Michael A. Fuoco: or 412-263-1968.


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