The election season was in full swing in December when John Podesta, chairman of Hillary Clinton’s presidential campaign, had a conversation with billionaire philanthropist Herb Sandler about doubling his giving to Priorities USA, the chief super PAC supporting Mrs. Clinton.

Mr. Podesta quickly told his campaign to let Priorities know that the money was coming, according to emails purloined from his account and posted online by WikiLeaks. Two days later, the check came through: $1.5 million.

For a campaign whose official position is antipathy toward big-money political action committees, the Clinton operation was incredibly adept at using them — and may even have crossed the line into illegal coordination. The WikiLeaks emails hint at that kind of activity, and show the campaign breaking the spirit of the rules, though it would be up to the Federal Election Commission to determine whether a provable violation took place.

But the emails detail the extent to which the Clinton campaign was the super PAC and why Mr. Podesta’s staff labeled him “#ChairmanCash.”

Analysts said it’s likely that every major presidential campaign does the same kinds of things, though Mrs. Clinton is getting most of the attention because of how prolific her allied groups have been — and because her official position is that she wants to outlaw exactly what her campaign is doing.

“These memos are very helpful in not necessarily what’s illegal, but what is legal — and showing the kind of activity the FEC allows to go on,” said Larry Noble, a former top lawyer at the FEC and a prominent reform advocate who is now general counsel for the Campaign Legal Center, a watchdog.

Before Mrs. Clinton announced her candidacy, Mr. Podesta and his team talked about how to shift Priorities USA, which had been created to back President Obama in 2012, to serve Mrs. Clinton. That included vetting the super PAC’s board members.

In the days just before the campaign’s April 12, 2015, kickoff, Mr. Podesta and his team plotted how to steer billionaires to give to Priorities — with fossil fuel financier turned global warming activist Tom Steyer at the top of the list.

Once the campaign was launched, manager Robby Mook said the team needed to get Priorities “functional” in raising big money, then use the Republican candidates’ fundraising “to scare our people into giving bigger sums.” They also talked about how to rope former President Bill Clinton and Mr. Obama into fundraising for Priorities — though Mr. Mook said Mr. Obama is “kind of prissy” about super PACs.

#ChairmanCash

The most striking incident, though, is the Dec. 17 message in which Mr. Podesta recounts his talk a day earlier with Mr. Sandler. Mr. Podesta emailed the campaign finance team saying the billionaire, who had already given $1 million to Priorities in April 2015, was ready to bring even more cash.

“Can you or Charlie let Guy know that he is also prepared to double down on his Priorities support as well. Guy may already know that,” Mr. Podesta said in the email. Guy Cecil, a top aide in Mrs. Clinton’s 2008 campaign, is now the head of Priorities USA.

The day after the email, Mr. Sandler did, indeed, contribute, giving another $1.5 million. Those would be followed by a $500,000 donation this April and another $1 million in September.

The news of Mr. Sandler’s pending generosity was greeted warmly by the Clinton campaign.

“Huge,” emailed senior adviser Charlie Baker, who ironically worked for Priorities USA before he was hired onto the campaign.

Finance chief Dennis Cheng dubbed Mr. Podesta “#ChairmanCash” for his ability to bring in the money.

Neither the Clinton campaign nor Priorities USA responded to requests for comment on the exchanges, whose legality is questionable, analysts said.

“It could have been a violation of even the really bad coordination rules of the FEC,” said Craig Holman, a campaign finance analyst at Public Citizen. “If it’s just conveying that there’s a funder who wants to talk to you, that would not violate the rule. But if the campaign actually said the funder wants to double his contribution to you, that would violate the rule.”

He said every major campaign is likely engaging in questionable behavior with super PACs. If challenges are raised with the FEC, the commission probably would split on a 3-3 vote, he said, and it takes an affirmative majority to cite a campaign.

“It’s sad, but anything goes here,” he said.

Mr. Sandler, in an email to The Washington Times, said he “cannot confirm the accuracy of email correspondence” from the WikiLeaks releases.

But he denied any inappropriate communications from the Clinton campaign chief.

“Mr. Podesta has always only solicited funds for the Clinton campaign and he has been very clear about those legal requirements and limits. I have had separate conversations with Guy Cecil about contributions to Priorities USA,” Mr. Sandler said.

Priorities USA: $175 million

Super PACs proliferated in the wake of the 2010 Citizens United ruling at the Supreme Court, which found that groups have a First Amendment right to spend their cash on political advertising.

That freed them to raise and spend hundreds of millions of dollars in uncapped contributions — though under FEC rules super PACs are not supposed to coordinate political strategy with campaigns. That includes both advertising plans and fundraising beyond the federal hard-dollar limits.

At the presidential level, former Florida Gov. Jeb Bush, a Republican, and on the Democratic side, Mrs. Clinton have been the biggest beneficiaries of super PAC assistance.

Priorities USA reports having raised more than $175 million to aid the Democratic nominee. By contrast, the top super PAC aiding Republican presidential nominee Donald Trump had raised just $20.3 million, according to the Center for Responsive Politics.

Yet another Clinton-affiliated super PAC, Correct the Record, raised nearly $10 million. Created by prominent Clinton defender David Brock, that group is testing the bounds of coordination rules by arguing it’s allowed to talk with the campaign as long as it is acting primarily in cyberspace, rather than traditional television commercials or other campaign activity.

The WikiLeaks emails show the Clinton campaign was initially worried about coordination, and Mr. Podesta mocked Mr. Brock in the emails. But the campaign ended up working closely with the super PAC, including having an intermediary ask for $1 million donations.

Mr. Noble’s group filed a complaint with the FEC in early October arguing that Correct the Record and the Clinton campaign were engaged in illegal coordination.

“Because Correct the Record is effectively an arm of the Clinton campaign, million-dollar-plus contributions to the super PAC are indistinguishable from contributions directly to Clinton — and pose the same risk of corruption,” Mr. Noble’s group said.

All told, the Center for Responsive Politics says, super PACs have raised more than $1.5 billion this year to assist in presidential and congressional elections.

Tom Steyer

Super PACs give the wealthy a chance to have an outsized influence on elections, which is one of the reasons Mrs. Clinton publicly opposes them. But privately, her team worked to entice its own billionaires.

Among the targets the Clinton campaign hoped to rope into giving to Priorities USA were Jim Simons, Fred Eychaner, Michael Bloomberg and, perhaps most often, Mr. Steyer.

“Ideally, we ask Tom to host HRC’s first fundraiser in San Fran on May 8, raise all of his $$ through that event now, then he can spend the rest of the cycle on the IE stuff,” Mr. Cheng said in an email to top campaign officials just after the official campaign kickoff last year. IE stands for “independent expenditures, a shorthand for noncoordinated spending such as super PACs.

Mr. Podesta said he would rope Mr. Steyer’s attorney into the conversation about working with the campaign — prompting Marc Elias, the Clinton campaign attorney, to pipe up in the email chain and note that he is also Mr. Steyer’s attorney.

Mr. Steyer donated to several independent expenditures, but the lion’s share of his money goes to his own super PAC, NextGen Climate Action.

The Clinton team also kept a close watch on who donated to Priorities, and made sure Mr. Podesta personally called to thank them for giving, according to a call sheet in the leaked emails.

The call sheet included legal dos and don’ts. Mr. Podesta was allowed to offer thanks, including saying “it really means a lot to me and Hillary.” But he was not to ask for more money, nor was he supposed to give a direct answer if the donor himself proposed giving more cash.

“Clearly they’re very closely coordinated,” Mr. Holman said. “We find a level of coordination that’s somewhat breathtaking where they’re actually handing off fundraisers to each other, talking about potential strategizing with the other super PAC.”

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