In an unusual attempt to forge an alliance between two of the most prominent political families in American politics, John Coale, a Washington-area Democratic donor and onetime adviser to Sarah Palin, urged the conservative Alaska governor to use her political action committee to help retire the presidential campaign debt of Hillary Clinton.
Coale, a wealthy trial attorney and the husband of Fox News talk show host Greta Van Susteren, approached Palin with the improbable plan in February while in Alaska with his wife, who was taping an interview with the former Republican vice presidential nominee.
An outspoken Clinton supporter during the Democratic primary who switched his allegiance to the GOP ticket for the general election, Coale made his case to Palin at the Iron Dog snowmachine competition in Fairbanks, where Todd Palin was competing over Valentine's Day weekend. His broader aim, say Palin camp insiders, was to help Palin develop a relationship with the former first family that he thought could bolster the polarizing governor's standing with Democrats and independents.
Palin was amenable to getting acquainted with the Clintons but was skeptical of using her PAC to help the former first lady.
She expressed concern to aides about Coale's request that weekend and a few days later directed Meg Stapleton, an Alaska-based campaign aide, to tell Coale that she would not help retire Clinton's debt.
"While we appreciate your efforts and recognize that a friendship with the Clintons is appropriate, the governor believes (and I concur) that using SarahPAC to pay down Hillary's debt is not a prudent use of the money," Stapleton wrote to Coale in a Feb. 17 e-mail, a few days after he made his pitch to the governor. "Contributors who chose between heating their homes and sending in a contribution because they believe in Sarah would be crushed."
But GOP sources say that in conference calls and e-mails with Palin advisers over subsequent weeks, Coale continued to raise the prospect of using SarahPAC to help Clinton, who was once public enemy No. 1 among the very Republicans who are Palin's most ardent followers.
"He thought the Clintons could rein in some of the Democratic firepower aimed at her," said a dumbfounded Republican privy to the discussion who advocated fiercely against the idea.
A former Clinton aide hadn't heard of the plan but deemed it "not rooted in anything that would touch on reality."
Coale conceded that he urged Palin and her advisers to consider helping Clinton, but he said it was part of a larger campaign to align the Alaska governor with prominent women in politics, including Republicans Meg Whitman and Carly Fiorina, both of whom are prospects for elective office in California.
"It was a women thing and not a Hillary thing," said Coale, who was angered at what he saw as sexism aimed at Clinton during last year's campaign and who has long taken an interest in promoting female politicians.
He sought to minimize just how much Palin could have done, noting that the PAC could give only $5,000 to help with Clinton's debt - a modest sum, given the former first lady's $2 million-plus campaign debt.
But Coale is candid about his efforts to create an unlikely bond between the ultimate Democratic power couple and the Alaska duo that so many liberals revile, noting that he had pushed the Clintons to get to know the Palins.
Former President Bill Clinton placed a friendly call to Palin after the election, and Coale sought to use that as an opportunity to play matchmaker.
He said he tried to set up a visit between Bill Clinton and Palin in Alaska earlier this year when the former president traveled to Asia, but Clinton wound up traveling there through Europe.
Stapleton, the Alaska governor's aide, said the Palins were open to working with the former president on Alaska-related policy issues such as seafood or arctic climate change, but not on anything political.
It may not have mattered. Clinton spokesman Matt McKenna said Coale suggested that the former president and Palin get together, but the former president's office declined.
"With these people from the opposite side, I'm trying to turn down the volume a bit on the attacks," Coale said. "The more people meet each other and actually talk to each other, the volume will come down."
Pam Pryor, a Washington-based Palin adviser, defended Coale, calling him a "networking hound" who was only trying to help connect friends.
"There's a real difference between setting up bipartisan friendships and politics," said Pryor, a Republican and former Capitol Hill aide.
Palin allies lament that Coale's efforts with the Clintons are symptomatic of a chaotic post-election period.
First, there were gossipy stories both before and directly after the presidential election that featured anonymous John McCain aides mocking Palin as a know-nothing diva - accounts that left the governor and her small inner circle wondering who their true friends were outside Alaska.
Without trusted and experienced hands to help manage the governor's political affairs, hundreds of letters stacked up in Palin's garage, many of them invitations to events. If nothing else, the governor needed a political entity to at least pay for the postage for the replies.
Coale, who accompanied Van Susteren to Alaska immediately after the election when the Fox News host traveled there for a post-mortem interview with Palin, helped fill the void by offering to help set up her PAC.
Soon after the PAC began operating in January, however, a series of embarrassing miscommunications took place.
Palin was invited to and seemingly accepted invitations to events in the "Lower 48" but then wound up backing out when her Alaska-based staffers said they knew nothing about the plans. Palin allies say that in some cases, event organizers let it be known that the governor was coming when she had not actually confirmed her appearance.
Advisers say the Palin camp was paralyzed by divisions between state-based advisers who wanted Palin to focus on Alaska, with an eye on restoring her political standing in the state ahead of a potential reelection campaign, and those who wanted her to capitalize on her celebrity and take a higher profile in national politics.
Coale fell into the latter camp, according to sources.
"He would say, 'She needs to get out and travel the country,' and we would say, 'No, she needs to govern Alaska,'" recalled an adviser in the Alaska-first camp.
With only occasional departures, Palin has now settled on focusing her energies at home. While Palin recently joined a group of top Republicans in a well-publicized effort to rebuild the party, it came only after questions were raised about her absence. But advisers indicate that she'll weigh in only on Alaska-centric issues such as energy.
And of the thousands of invitations she gets, Palin plans to attend only out-of-state events that have an Alaska hook.
"As we've been trying to make clear, the governor is entirely focused on Alaska and not on the national scene," said Stapleton. "That is to the frustration of some who have their own political ambitions for her."
Palin has set up a Twitter feed that is almost exclusively focused on Alaska issues and canceled a scheduled appearance at the White House Correspondents' Association Dinner after a spate of floods hit Alaska. Todd Palin, however, still attended the dinner as a guest of Fox News and was escorted by Coale and Van Susteren.
Asked about Palin's decision to keep her focus on Alaska, Coale replied: "They're doing whatever they're doing."
He said after helping to get the PAC off the ground he had limited his involvement and denied that his diminished role had anything to do with his Clinton plan or the scheduling miscues.
"I'm friends with Todd and Sarah - I'm not advising them politically," Coale insisted.
Some top Republicans who are sympathetic to Palin understand her short-term political imperatives at home - her approval numbers have fallen considerably from last year, when McCain would often defend her against critics as "the most popular governor in America." They compare her to an incredibly gifted athlete with raw skills but no coach to help her develop a pro game.
"What she really needs is somebody who has good political sense to move to Alaska," said a Washington-based Republican who wants her to succeed. "And until that happens, she is going to continue floundering."
Ben Smith contributed to this story.
By Jonathan Martin