During the summers he indulged in one local campaign after another, usually working for losers, but building a knowledge about Boston politics. Even during his hours at summer jobs he breathed politics. "'He used to continually talk about his political ambitions," said James Little '72, a coworker with DiCara at Kelly's Landing soda shoppe one summer. "I remember his having ambitions of being mayor when he was 16."
Even those who despised his political nature grudgingly admitted that he was competent. Finally the big day came. The Boston Latin Class of '67 was electing a president, and DiCara won by what was apparently a wide margin.
His new office led him into a number of disagreements with the headmaster. "It was a clash of strong personalities," one student explained. DiCara tried to push reforms which traditionalist BLS was not eager to enact.
"The headmaster hates his guts," one classmate asserted. "He doesn't recognize him as an alumnus. He wouldn't even write him a recommendation for Harvard." Another said, "O'Leary mentions him as often as possible in a bad light. He doesn't like to have him in the school to visit."
Nevertheless, DiCara got into Harvard and was flown to Dallas to receive the Golden Scroll for the Promise of Greatness from the American Academy of Achievement. The world watched.
At Harvard, DiCara rented refrigerators. He has trotted around for Harvard Student Agencies (HSA) each September, earning money and shaking hands. He memorized students' hometowns and high schools. As he continued to immerse himself in things political, acquaintances started asking him when he was going to run for a real office.
While he's been here, opposition to him has centered not only on his manner, but on his political views as well. DiCara is somewhere between moderate and liberal, and this has not set well with everyone at Harvard. Last Fail, when there was opposition to Quincy House's intention to send a representative to the controversial CRR (Committee on Rights and Responsibilities), DiCara was rather irritated. "This is not the kind of issue that is top priority," he said at the time. "Kids are starving in Dorchester."
Earlier he had created some derision for picking some of the numbers (264-272) in the nation's first draft lottery since the 1940's. He was on a Selective Service advisory committee at the time and was picked as the Massachusetts representative for the televised drawing in Washington. Picking such high numbers made him feel "pretty darn good," and he himself ended up with number 208. "I've had a lot of second thoughts, but I'd do it again," he said on Valentine's Day.
His second thoughts stemmed partially from a few hate phone calls to his Dorchester home. One caller warned that he'd be killed.
Besides his political activities, DiCara keeps busy with civic organizations. He is Cubmaster of Troop 66, a committee type at the Knights of Columbus, an assistant in the CYO program at St. Gregory's, and a member of the Hyde Park Most Precious Blood Catholic Young Adult Club.
DiCara returned Thursday from a CYO ski trip to Lake George, N.Y. Though he refused to get on skis, he agreed to be one of the chaperones for a group of 140 teenagers. One of his tasks was to check suitcases for liquor before departure. DiCara, who looks much older than 21, recalled with a laugh one special episode on the trip. "I was dancing with a couple of gals and really keeping up with them. I love to dance and I was wearing this white turtle neck, pretty avant-garde for me. So I got a standing ovation from the band for bridging the generation gap," he said.
DiCara had been toying with the idea of running for City Council for quite a while, but didn't make the final decision until January 10 at a meeting of his "chief supporters." He will officially enter the primary June 14 with a statement at McKeon Post in Dorchester, but he's already passing around the navy blue campaign buttons. "Look, the people want them," he told roommate Henry Kettls a week ago. Kettle had started DiCara's campaign with a donation of one cent. Since then another $5 has been contributed, but DiCara has used $500 of his own.
If elected, DiCara believes he will join James Michael Curley and Francis "Sweepstakes" Kelly as the youngest members ever elected to the Council. He will be 22 by then. But he would be the youngest one ever elected at large since Curley and Kelly were elected while running as ward candidates. But DiCara is not playing up the youth issue.
The Council is made up of nine members elected at large. All nine seats are available this November, and since a number of top councilmen will probably get in the mayoral race against struggung incumbent Kevin White, DiCara figures his chances are better than usual. "I don't think any of those seats are safe," DiCara said Sunday, even though he expects four to six incumbents to run. He estimates that 40 persons will be in the September primary, with 18 going on the November ballot.
"I have to finish in the first 12 or 13 in September to have a good shot," DiCara said. Like any politician, he refrains from talking down his chances, which he characterizes as "darn good, darn good." DiCara predicts that his success will vary directly with the funds he raises between now and July. The target is $25,000 to $30,000. "If I can raise that amount of money and can't win, well, that's pretty bad," he mused.
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