Instead, policemen angry at working for two years without a contract shouted his name at noisy protests last week that delayed the start of preparations for the July 26-29 political gathering.
Making matters worse, a major highway and railroad station have been ordered closed during the convention, angering business owners and commuters who foresee days of traffic chaos.
Hometown son Sen. John Kerry (search), the party's likely presidential nominee, angered residents even further by briefly flirting with the idea of not accepting the nomination at the convention.
And two different groups say the convention will be far from the economic engine Menino has promised and predict the city will lose money due to the cancellation of other events and the effect on the work force.
Menino's quest for a legacy seems to be turning into more of a nightmare.
"It's more difficult than I thought it would be, no question about it," Menino told The Associated Press in an interview Monday. "There are so many moving parts. If I were controlling all the moving parts, it would be much easier. But I'm not."
Some political analysts say history will gloss over these pre-convention glitches if the event itself proves a success, but they acknowledge that the convention may have a different effect on Menino than many once imagined.
"The buck stops on his desk for fighting so hard for this," said Jeffrey Berry, who teaches political science at Tufts University. "It's not going to be seen as Menino's folly, but it's not going to be seen as his finest hour, either."
A three-day shutdown last week of the FleetCenter, the convention site, was the most dramatic and potentially damaging incident thus far. Democratic National Committee officials estimate that each lost day of work cost about $100,000. They also had to postpone an inspection of the site by the national media, which had been scheduled for Tuesday.
After months of assurances that Menino's labor troubles would not affect the convention, DNC officials were left frustrated, angry and powerless to influence a long-simmering conflict between a mayor and his police union.
The picketing ultimately ended and work got under way, but not before projecting another image of chaos and discord. Menino's staff met in mediated negotiations with the Boston Police Patrolmen's Association from Sunday evening to early Monday morning before adjourning without an agreement. Talks are to resume Wednesday.
After losing a bid for a political convention in 2000, Menino and his staff worked tirelessly to land one this year. They lavished Democratic Party officials with lobster, Red Sox tickets and tours of Beantown and even distributed cell phones, which they then used to bombard the officials with text messages trumpeting Boston's glory.
The effort paid off in November 2002, when the DNC announced that Boston would host the first national political convention in its history.
"Menino wanted this and believes this convention can be a legacy for him," said Michael Goldman, a longtime Democratic political consultant. "In the long run, this will either be perceived as a huge success or seen as a huge mistake. But mayors that don't take risks aren't remembered for being great mayors."
Menino is the city's longest-serving mayor, having held office since 1993. The son of a factory worker, the 61-year-old one-time union member had been considered, until recently, a friend of labor. He counted labor unions among his strongest supporters during his two re-election campaigns.
Menino appeared upbeat Monday while meeting with reporters, despite the seemingly endless stream of negative headlines. He said he had no regrets about his efforts to land the convention.
"In the long run, this is going to be beneficial to the city of Boston, both prestige-wise and in terms of bringing other conventions to Boston," Menino said. "The economic impact will be tremendous. And we'll have fun for those four days in July."