It was a big day for Revere.
A group of former Boston Bruins stars, including Rick Middleton and Reggie Lemelin, would skate in a charity hockey game to raise money for the Columbus Day Parade, a pageant of antique cars, nautical-themed floats, and waving politicians revived after a five-year hiatus.
The game, held at Cronin Memorial Rink in the fall of 2013, needed to be insured by the city. And then-Mayor Daniel Rizzo signed off on the purchase order himself, according to documents obtained by the Globe.
The vendor: Rizzo Insurance Agency, his family firm.
Just a small amount of money — $285 — changed hands. But good government advocates say the move is a blatant violation of state ethics law, which forbids municipal officials from participating in matters in which they have financial interests.
“You shouldn’t be doing business as a private individual with the city you’re leading,” said Pam Wilmot, executive director of Common Cause Massachusetts. “It’s a matter of providing clear loyalty to the city, versus your own financial self-interest.”
It is one of a series of small-bore ethical issues hanging over Rizzo, a Democrat, as he enters the final days of a tightly contested state Senate race. The Globe also found that he signed off, as mayor, on a contract with a nonprofit agency insured by Rizzo Insurance, though the move may have been permitted under state law.
Additionally, documents show Rizzo continued using his city-issued E-ZPass transponder after he left office at the end of last year, allowing taxpayers to pay his tolls on the Tobin Bridge and at the Sumner and Ted Williams tunnels for two months until the new administration cut him off.
Scott Ferson, a spokesman for Rizzo’s Senate campaign, declined to discuss any of the findings in detail. But he dismissed them as minor issues and suggested they could be traced back to rivals for the Senate seat.
“It’s clear that Dan’s opponents understand that he’s ahead in this race and he’s going to win,” said Ferson. “They’re looking for anything to try to take him down. And this is very thin stuff to be throwing this close to the election.”
Rizzo is considered one of the top contenders in the race to succeed former state senator Anthony Petruccelli, an East Boston Democrat who stepped down to take a job as a lobbyist. The district spans neighborhoods in Revere, Winthrop, Boston, and Cambridge.
The race has grown testy in recent weeks. One Rizzo supporter placed an advertisement in a Revere newspaper attacking a Democratic rival, state Representative Jay Livingstone, for sponsoring legislation that would require public notice before installing video surveillance equipment.
The ad said the bill would give “bad guys the heads up as to where camera[s] are located.” It also said that, had the measure been law prior to the Boston Marathon bombings, “the Boston Bombers could have gone on to New York City for the second phase of their attack.”
Livingstone criticized Rizzo for the ad at a recent forum, suggesting it was exploiting the bombings for political gain. Rizzo said he cannot control what his supporters say, but criticized Livingstone for the legislation.
Rizzo served a single term as mayor of Revere before losing a tight reelection fight last fall, settled with a December recount at the Revere High School Field House that left him trailing by 108 votes.
As mayor, he signed a contract with the nonprofit Revere Beach Partnership to provide family-oriented activities along Revere Beach, including what was then called the Revere Beach National Sand Sculpting Festival, which draws several hundred thousand people.
The city required Revere Beach Partnership to show proof of insurance to get the contract and the nonprofit submitted a “certificate of liability insurance” from Rizzo Insurance.
State law prohibits municipal officials from indirectly benefitting from a city contract. But that provision would probably only apply if Revere Beach Partnership specifically purchased the policy from Rizzo Insurance to get the city contract. If the partnership already had the policy in place, as a general protection, then Rizzo would likely be in the clear.
Revere Beach Partnership officials did not respond to calls and an e-mail for comment. And it’s unclear from the documents obtained by the Globe whether the policy was purchased as a general protection or not.
Wilmot, of Common Cause, said it’s best for a public official as powerful as a mayor “to really keep an arm’s length from dealing directly or indirectly” with a family business, whatever the legal ramifications.
One section of the state law attempts to get at this sort of broader ethical concern, barring public officials from acting in any manner that would cause a “reasonable person” to conclude that they could be unduly influenced.
The law provides an exemption, though, for those who publicly disclose the relevant circumstances. And Rizzo did file a disclosure, at the time, about his 50 percent ownership stake in Rizzo Insurance and its business dealings with Revere Beach Partnership.
As mayor, Rizzo had a city-issued E-ZPass, which he continued to use even after leaving office. City records show that he racked up $55 in tolls at taxpayer expense in January and February of this year — a bill city officials say they may not pay. Rizzo used the E-ZPass for the last time on Feb. 24, a $2.50 trip over the Tobin Bridge. That same day, the city cut off his E-ZPass.
The notation on the account summary read simply: “Transponder — Lost/Stolen.”David Scharfenberg can be reached at email@example.com. Follow him on Twitter @dscharfGlobe.