Menino holds big financial lead

Heading into June, Menino, who is seeking a record fifth term, had more than $1.3 million in the bank, compared with Flaherty’s $542,000 and $199,000 for Sam Yoon, another city councilor challenging the mayor.

Flaherty, a five-term councilor at large from South Boston, is the council’s most prolific fund-raiser ever, but he is learning firsthand how difficult it is to keep pace with an incumbent who in July will become the longest-serving mayor in the city’s history. Menino, like other sitting mayors, can count on financial support from real estate development interests, city employees, and companies that are regulated by or do business with City Hall.

So far in June, Menino’s campaign has already taken in $135,000, according to reports filed with the state, and he has several more fund-raising events scheduled before the end of the month, said his campaign treasurer, David Passafaro. The campaign should raise at least $175,000 in June, he said, marking the fourth consecutive month eclipsing the $100,000 mark.

Flaherty’s campaign has collected $108,000 thus far in June and will host four more fund-raisers before the month ends, said Natasha Perez, the campaign’s communications director.

Maura Hennigan, the last councilor to run against Menino, is still paying a steep price for her doomed challenge in 2005, as she pays down the $700,000 she borrowed to finance most of her campaign.

“Once you announce, there’s a real chilling effect,’’ said Hennigan, who was elected to a Suffolk County clerk of courts post the year after her defeat. “People who like you and have supported you tell you they don’t want to rock the boat, especially if they have development projects or need permits from the city. . . . But this is the business; it’s not for the weak of heart.’’

Jim Spencer, chief strategist for Yoon, called the state’s campaign finance law, with its $500-per-year limit on individual contributions, “an incumbent protection’’ mechanism. “Anyone challenging him has a lot of hill to climb,’’ Spencer said, explaining why Yoon has generated so many contributions from outside Massachusetts. About 54 percent of the $207,000 Yoon has collected in the first five months of 2009 comes from out-of-state donors, records filed with the state show.

By contrast, Menino, who raised $552,000 from January through May, received about 5 percent of his total from out-of-state donors. Flaherty, who collected $239,000 in that period, took in 4 percent of his contributions from outside Massachusetts, according to data compiled by the state Office of Campaign and Political Finance.

Conversely, 47 percent of Flaherty’s total amount raised and 41 percent of Menino’s came from Boston residents. Only 15 percent of the money donated to Yoon’s campaign this year is from city residents, the state data show.

A third challenger, South End businessman Kevin McCrea, had raised less than $4,000 through the end of May and had loaned $10,000 to his campaign.

With three months until the preliminary election, critical decisions loom on spending, particularly for the challengers, only one of whom is likely to qualify for the Nov. 3 ballot. Menino led by a wide margin in a Boston Globe poll conducted early last month. Menino’s camp must weigh the value of heavy spending to build a victory margin in the Sept. 22 preliminary election at the expense of holding back cash for the six-week final campaign, when it becomes more difficult for any candidate to raise substantial additional sums.

Through Memorial Day, Menino had spent $624,000, far more than Flaherty ($287,000) and Yoon ($145,000) combined. Menino’s expenses include more than $100,000 on television ads in late April and early May, soon after he announced he would run for reelection.

His campaign spent almost as much to host fund-raising events ($80,000) as Flaherty’s campaign spent on consultants ($87,000), including about $32,000 to firms formed by Paul Tewes, a key operative in Barack Obama’s presidential campaign.

The Flaherty campaign has invested heavily in technology, for databases with voter information, and for its website, which it has been using to reach voters who do not typically vote in municipal elections. Boston-based Sage Systems was paid $100,000 over five months to provide those and other services. Flaherty’s campaign has also spent more than the other campaigns on printing and mail ($46,000), traditionally a tool to contact voters who turn out regularly for local elections.

Yoon’s campaign, by contrast, has built its website with a do-it-yourself package of technology tools and volunteer labor, said Spencer. The Yoon campaign is trying to garner more attention in the liberal blogosphere in an attempt to boost fund-raising. Strategist Joe Trippi, a veteran of John Edwards’s 2008 presidential campaign and Howard Dean’s campaign in 2004, has been paid $6,000 through May by the Yoon campaign.

The Yoon campaign also spent about $7,200 on its out-of-state fund-raising trips. As a city councilor, Yoon has proposed Boston move to a car-sharing service to save money on fleet expenses. His campaign has used Zipcar, the Cambridge-based service, paying six bills totaling $549.