Now, in a new role, he is putting his network and negotiation skills to work for a different group: disadvantaged young people from the poorest neighbourhoods.

Recently, he made a career shift, choosing to step down as a partner at McCarthy Tétrault to pursue other interests while staying on part-time as a strategic adviser.

"A lot of my job has been to get people to understand other people's positions and bring people together," Mr. Diamond said. "If I can make some of the companies understand the issues facing the city and make it an even better, greater and safer city, that is the job I want to do."

Last week, in a slightly premature announcement, Mayor David Miller revealed that Mr. Diamond, in a volunteer capacity, will lead a stepped-up effort by business, the city and community groups to crack open the job market for young people, especially minorities.

Over the summer, Mr. Diamond will assemble a committee of top business leaders, to be named this fall, to make peer-to-peer contacts in the corporate world to promote jobs for young people.

"He is passionate about Toronto, he's a well-connected lawyer and shows terrific leadership," Mr. Miller said. "I hope his work, with the Toronto Board of Trade, will demonstrate to young people in Toronto's poorest neighbourhoods that they, too, have real opportunities in this city."

The addition of Mr. Diamond comes as public- and private-sector groups agree that permanent jobs for young people, especially those at risk of falling through the cracks, are essential to combat gun violence and poverty.

But those same groups, especially from the private sector, also recognize that achieving the goal is easier said than done.

In March, for example, the board of trade announced an ambitious campaign to encourage employers to hire young people from poor neighbourhoods, setting a target of 1,000 by Sept. 1. As of last week, the Youth One initiative had netted only 82 part-time jobs.

This tally compares with 985 part-time jobs for youth through various city departments and agencies, including parks and recreation.

As well, the provincial government has earmarked $2-million this year for 750 temporary jobs in 13 vulnerable neighbourhoods identified by the city and the United Way.

Board of trade president Glen Grunwald calls the effort of his group, which works closely with the city to match youth and employers, "a work in progress."

He conceded "it will take more time to get the message out," adding that some employers are nervous about hiring at-risk young people, some of whom have had minor brushes with the law. But everyone in the Youth One project is vetted by the city and community agencies, which also provide job-related support, such as how to prepare for an interview.

Mr. Grunwald said the board is determined to stick to its goal, even if the deadline is extended beyond September.

That's where Mr. Diamond comes into the picture.

Several months ago, after a meeting with Ontario Chief Justice Roy McMurtry, head of the mayor's community safety panel, Mr. Diamond agreed to get involved with the campaign.

"I came to the conclusion that the city of Toronto has been very, very good to me and this is a way, if I could make a contribution, to have a positive program for the city," Mr. Diamond said. To break the current cycle of violence, he said, "there is an obligation on all of us to do something. We can't sit back."

But he and city officials warn it will take time to win over skeptical employers and make a real dent in hard-pressed communities.

In his new role, Mr. Diamond said, he will be a go-between, tapping his network of corporate contacts while advising city officials on how to simplify programs so businesses are able to hire talented young people.

"This is not a handout at all. There are qualified young people from these areas who, for whatever reason, may not get an equal opportunity to get placements at these jobs."

Despite the relatively strong local economy, some young people feel shut out of the job market, said Manjit Jheeta, manager of the city's community safety secretariat.

"Many come from neighbourhoods and communities that have been stigmatized," she said. "Young black men say it is very difficult to get their foot through the door.

"I've been at meetings where young people tell me: 'We never get to sit down with the people who can open doors for us.' "