Marden was more than just LePage's friend and employer; he served as his political mentor as well. In 1992, Marden had shocked many in Waterville by winning a vacant state senate seat long held by Democrats, defeating a better-financed Republican primary challenger along the way. "I think they need some business application to the problems in Augusta," he said during the campaign. The state had "gone overboard on environmental issues" and banks were hamstrung by regulations. He lasted just one term. "He didn't know what was going on and he did not like the fact that he wasn't the absolute boss," says Ruth Joseph, a Waterville Democrat who knew Marden well and served in the same legislature before becoming mayor. "Mickey had the same personality as Paul, and certainly was an advisor to Paul as he entered politics," she said, an assessment endorsed by another source close to Marden. (The governor's staff would not comment on this.)

In 1998, LePage successfully ran for a seat on Waterville's city council in Republican-leaning Ward 1, allegedly motivated by his displeasure with Mayor Ruth Joseph's controversial plan to sell a piece of city-owned land for $1 to facilitate the construction of a park and a $1.6 million administrative building. Taking office amid the Monica Lewinsky scandal, he spearheaded a ten-month investigation of Joseph, accusing her of "questionable management practices" and 11 possible violations of the city charter and ordinances, and demanding her resignation. "It's a terrible, terrible situation," he told a reporter. "I feel like we were back in the 1950s, going after gangsters." Joseph refused to step down, saying it was the dirtiest political move she'd ever seen. She was recalled in a special election shortly thereafter by a 2-1 margin.

"It was just politics," Joseph recalls. "They probably thought I was going to be mayor for the rest of my life, because of my [seven terms] in the legislature . . . Paul saw what he thought was an opportunity, so he did what he could to get where he wanted to go."

Meanwhile, LePage was building his profile. He rubbed elbows with other Waterville-area Republicans at Rotary, the Elks Lodge and the country club. He was active in the chamber of commerce — which would later name him businessman of the year — in the Maine Forest Products Council, and in the High Hopes Clubhouse, which placed mentally-challenged workers with jobs at Marden's and other employers. Marden's continued to expand under his leadership, and Ward 1's voters reelected him in 2002.

He and Ann took many of their vacations at SuperClubs Breezes Runaway Bay, a gated PGA golf resort in Jamaica. There, in 2002, LePage decided to do his part to pay-it-forward, volunteering to mentor his golf caddy's 17-year-old son, Devon Raymond. The LePages took Raymond in, raising them as if he were their son, sending him to Husson and, later, Alabama's Grambling State University. (The governor's office has stated that Raymond has been in the US on a student visa, and he is now pursuing graduate studies in Louisiana.) LePage would later say he had adopted Raymond and that he was an orphan. In fact, at least one of his parents was alive and living back in Runaway Bay, where Devon had been the "head boy" his school, a member of the Jamaican national junior golf squad, and a founding member of the junior golf summer camp held at the resort. LePage would also raise his adoption of Raymond as a shield against accusations of racism, first when demanding Governor John Baldacci endorse the questioning of anyone who looked like they might be an immigrant in 2004, and again after telling the NAACP to "kiss my butt" on the eve of the 2011 Martin Luther King holiday.

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