Michael Liberty, the former Portland real estate developer who has spent nearly $100,000 on next week’s Democratic primary for Cumberland County sheriff, has a long history of political contributions, but this is the first time he has given so much money in a relatively low-level election.

The reason remains a mystery. Liberty has not responded to requests for comment through his Portland-based company, The Liberty Cos.

Among the candidates Liberty has supported is Susan Austin of Gray, who was a Republican state representative from 2002 to 2010. Austin said Liberty is her husband’s cousin and she has known him since he was “a little boy.” Liberty donated $500 to Austin’s first legislative campaign.

Austin said she believes that Liberty picks candidates and causes to support based on the people, rather than the ideology. She could only speculate about why Liberty has invested so much in the race between Michael Edes and Sheriff Kevin Joyce, who has been targeted by radio ads and mailings funded by a political action committee backed by Liberty.

“I know that Michael is loyal, almost to a fault, to his friends and the strong relationships he has in his life – he’s always been that way,” said Austin, who is running again as a Republican for the District 67 House seat.

The radio ads and mailings accuse Joyce of mismanaging the Cumberland County Jail. The ads highlight two incidents in which inmates in the maximum-security wing got out of their cells to have sex with other inmates of the opposite sex.

Edes, a former state trooper, denounced the ads, which were paid for by Citizens for a Safe Cumberland County. Filings with the state Commission on Governmental Ethics and Election Practices show that the PAC received all of its funding from a company in Florida in which Liberty is listed as an officer.

The $100,000 donation to the PAC is a highly unusual – if not unprecedented – level of spending for a Maine county sheriff’s primary. Edes said he and Liberty have been friends since childhood but haven’t spoken since last year. It would be illegal for Edes to coordinate his campaign activities with the PAC.

MOST DONATIONS GO TO REPUBLICANS

Filings with the Federal Election Commission and the state ethics commission indicate that Liberty has donated mostly to Republicans in recent years.

In 2012, he contributed $10,000 to the Republican National Committee and spent more than $4,500 on Republican Mitt Romney’s presidential bid.

From 2012 to 2013, he gave about $20,000 to the Maine Republican Party and $10,000 to the Romney Victory fund. He also gave $2,600 last year to Republican Bruce Poliquin, who’s now a candidate in Maine’s 2nd Congressional District.

In 2012, Liberty gave $2,500 to independent Sen. Angus King’s campaign.

He also has given to Democrats, including Ethan Strimling’s congressional campaign in 2007.

Liberty’s donation to the PAC in the sheriff’s race was made through a Florida-based limited liability company, Brentwood Investments.

Brannon Carter, an officer for the PAC, has not returned repeated calls for comment. The voicemail box for the PAC’s treasurer, Christina A. Massengill, was not accepting messages.

David Sorensen, spokesman for the Maine Republican Party, would not comment on Liberty’s donations, other than to say “he like anybody has a right to support any candidate or causes he feels strongly about.”

Strimling, director of the Portland-based nonprofit organization LearningWorks, said he has never met Liberty and only spoke to him on the phone in 2007. He received a $2,300 donation from Liberty.

“A lot of support is built on relationships, as opposed to ideology,” Strimling said.

That may shed light on Liberty’s support for Edes, who switched his voter registration last year from unenrolled to Democrat.

Edes said that as a longtime president of the Maine State Troopers Association, it was easier for him to deal with various governors over the years if he wasn’t enrolled in one of the parties.

NO STRANGER TO CONTROVERSY

Liberty, whose current projects include Mozido, a mobile payment company, is now involved primarily in real estate development outside Maine, but he was a highly visible and controversial figure in the 1980s.

He developed two office towers at 100 Middle St. and the Chandler’s Wharf waterfront condominiums in Portland. Another large waterfront project he proposed prompted a referendum that led to a ban on non-marine uses of the waterfront, a rule that has been relaxed by Portland officials only recently.

In 2006, the federal Securities and Exchange Commission filed a civil action against Liberty, accusing him of misappropriating $9 million from a private venture capital fund whose largest investors were public pension funds.

Liberty strongly denied the allegations, but reached a confidential agreement with the SEC in 2010.

According to a biography posted on his company’s website, Liberty is an active member of Business Executives for National Security, a nonpartisan group that works with the departments of Defense, State, Treasury and Homeland Security and the Central Intelligence Agency.

He also founded the Liberty Family Foundation, a nonprofit that, according to its website, “believes helping those in need will inspire other civic leaders and individuals to do the same.”

According to filings with the Internal Revenue Service, the foundation contributed $48,558 in 2011 to causes in Maine, New York, Florida and New Hampshire, mostly in the form of scholarships and assistance to youth programs and indigent families.

Randy Billings can be contacted at 791-6346 or at:

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Twitter: @randybillings