A political action committee backed by Portland-based businessman Michael Liberty has poured nearly $100,000 into campaign mailings and radio ads targeting Cumberland County Sheriff Kevin Joyce, who is being challenged by retired state trooper Michael Edes in the Democratic primary June 10.

Edes said Friday night that he and Liberty have been friends since childhood, but he hasn’t talked to Liberty since last year and has not coordinated any of his campaign activities with the PAC, which would be a violation of campaign laws.

Edes posted a note on his Facebook page Thursday saying the radio ads, which criticize Joyce’s management of the county jail, don’t align with his attempt to run a positive campaign, and that he is asking that the ads be pulled.

The ads focus on two incidents in the past two years in which male inmates in the maximum-security wing of the county jail got out of their cellblocks and into a maximum-security area for women, where they had sex with female inmates in the women’s cells.

The mailing features newspaper accounts of the incidents, with the paragraphs set off with “XXX” in pink.

Any political action committee, particularly one backed by a six-figure donation, is unusual and possibly unprecedented in a Maine county sheriff’s primary. The U.S. Supreme Court’s 2010 ruling in Citizens United v. Federal Election Commission lifted caps on the amount of money companies can contribute to PACs.

According to campaign reports filed Friday, Citizens for a Safe Cumberland County had a sole contribution of $100,000, from Brentwood Financial LLC, a company that lists an address in a strip mall in Orlando, Fla.

Liberty is listed as an officer of the company in its corporate filing on the Florida Department of State’s website.

Brentwood Financial isn’t listed on Liberty’s website among the dozens of companies he owns or has invested in, but an officer of the PAC, Brannon J. Carter, provided state elections officials with an email address for a company called Mozido. The firm, a start-up that hopes to provide payment processing systems to companies and mobile phone users, is one of Liberty’s biggest current projects.

Liberty is primarily involved 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.

Liberty did not respond to an email seeking comment Friday night. Carter did not respond to an email, and his cellphone’s voicemail box was full.

A phone number for Christine A. Massengill, listed as the PAC’s treasurer, connects to a Scarborough company. She did not respond to a message left there Friday night.

Edes said Carter and Massengill have been his friends for several years but he hasn’t contacted either of them directly about the PAC.

As of Friday, the PAC had spent all but about $1,200 of the $100,000. More than $35,000 went to the production of, and postage for, the mailings. The radio ads cost nearly $34,000 to produce and air, according to the PAC’s report.

The rest of the money went to taxes, and legal and banking fees, along with $5,000 in consulting fees to Portland-based Vital Impact Campaigns.

Beyond the PAC, Edes’ own campaign is expected to significantly outspend Joyce in the race. Edes said he has held more than a half-dozen fundraisers and expects to spend about $40,000 by the time the primary votes are cast. The winner will have no Republican opponent in November.

Joyce said he will spend the same amount – about $14,000 – that he spent when he ran unopposed four years go. A major part of that will go to radio ads, beginning Monday, in which he is endorsed by his two predecessors as sheriff, Mark Dion and Wes Ridlon.

With the PAC spending, Joyce stands to be outspent in the race by about 10-to-1.

“That’s a lot of money to get me out of the seat and it’s definitely out of the ordinary to have a political action committee come up and do this,” Joyce said.

Edes said he has to spend more than Joyce to overcome Joyce’s stronger name recognition from four years in office.

“I think he’s banking on the fact that he’s the incumbent,” Edes said.

He said Joyce should have stepped up his fundraising because he should have been aware that a challenge was coming. Edes almost ran four years ago, but held off until he put in enough time as a state trooper for full retirement pay.

Edward D. Murphy can be contacted at 791-6465 or at:

[email protected]