He owed hundreds of thousands of dollars to banks, the government, and several casinos in 2008; he was sued for allegedly cashing $210,000 of worthless checks in 2009.
Between 1999 and 2007, two local craftworkers' unions won several lawsuits against him for failure to pay bills on time, often for tens of thousands of dollars.
Now, local investigators are probing Canazaro's complex financial web, trying to see what role his debts and businesses may have played in Jan. 18, the final day of his life, when two armed robbers entered his house through a first-floor window, tied up him, his girlfriend, and younger son, and eventually killed him and left him dead on the floor of his garage.
The robbers made off with several guns from Canazaro's collection, police said, and a black Lincoln pickup that was recovered later that day in the Quakertown Plaza parking lot. They remain at large.
Authorities say Canazaro's home was targeted for robbery, but they have not said whether Canazaro was a target for murder.
They don't have suspects, Bucks County Assistant District Attorney Matthew Weintraub said Friday. And they have not released a cause of death, citing the open investigation.
Canazaro's financial history was only part of what detectives were examining as they searched for clues, Weintraub said.
"That's certainly an area that we're investigating," he said.
Court records show financial difficulties were a recurring issue in Canazaro's life.
His bankruptcy case, filed in 2008, laid out in detail how deeply he had fallen into debt: he owed about $6 million to banks; nearly $890,000 to casinos in Las Vegas, Atlantic City, and Biloxi, Miss.; and more than $500,000 in federal, state, and local taxes.
At the same time, he was claiming about $70,000 a year in income, records show, while leasing a Mercedes-Benz for $1,700 a month and paying nearly $2,400 a month in alimony.
In the eight years before his bankruptcy hearing, Canazaro was sued seven times by local unions, including Bricklayers and Allied Craftworkers Local 1 in Philadelphia and Local 5 in New Jersey, and lost at least four of the suits. The largest judgment was for $108,000 to Local 1 in August 2007.
A year after that case closed, Canazaro filed his bankruptcy suit, listing the $108,000 he owed the union. The union never received any of the money, Local 1 president Dennis Pagliotti said last week.
"Of course, we're not happy about it," he said by telephone, declining to elaborate.
Canazaro was described by friends and associates last week as gregarious and outgoing.
Paul Herron, a lawyer who, on behalf of clients, sued Canazaro over a $360,000 debt, said Canazaro never lost his upbeat demeanor throughout the dispute.
"I just recall him being kind of a happy-go-lucky guy," Herron said. "I don't ever remember him being an angry or difficult kind of a guy."
That sentiment was echoed by Gary Mezzy, Canazaro's divorce lawyer, who said Canazaro was a "bright spot" to talk with, despite going through a divorce and what Mezzy described as a contentious custody dispute.
John Lowe, who runs M-John's Automotive on Broad Street in Lansdale, a property Canazaro owned, said Canazaro was a friendly family man who loved his sons. Canazaro enjoyed hunting, Lowe said, but the two never had in-depth chats, despite a business relationship that spanned about 15 years.
John Lowe, who runs M-John's Automotive on Broad Street in Lansdale, a property that Canazaro owned, said Canazaro was a friendly family man who loved his two sons. He said Canazaro enjoyed hunting, but that the two never had in-depth chats, despite a business relationship that dated back about 15 years.
Ex-wife Valerie Canazaro said in an e-mail that Canazaro was "the funniest guy I ever met," and that he was proud of his two sons.
More than 100 relatives and friends gathered for a viewing and Funeral Mass at Mary, Mother of the Redeemer Roman Catholic Church in Montgomery Township on Saturday morning.
Outside the church, Joe Vitolo, whose wife was related to Canazaro, said whatever difficulties Canazaro had, he always enjoyed being around his sons.
"He was just a great family man," he said.
Contact Chris Palmer at 609-217-8305, firstname.lastname@example.org, or follow on Twitter @cs_palmer.