"My only objectives were to take stock, professionalize the foundation, build it for the future and build it in such a way that supported his work and my mom's," Ms. Clinton wrote in an email to her parents' closest advisers in November 2011, around the time she enlisted outside lawyers to examine the foundation's practices.
Though her housecleaning role had Hillary Clinton's tacit approval ("My mother strongly agreed," Ms. Clinton said in one email laying out proposed changes at the foundation), it proved not to be so simple. Her efforts set off a cascade of grievances, gossip and infighting as her ascendance diminished the longtime aides whom Mr. Clinton often referred to as surrogate children.
Ms. Clinton had already started to fret about the intermingling of foundation business with Teneo, the corporate consulting firm co-founded by Douglas J. Band, one of her father's closest aides. She suggested an audit of the charity and wrote that she was concerned that Teneo's principals had been "hustling" business at foundation gatherings.
Ms. Clinton, 31 at the time, had held various jobs, including positions at McKinsey & Company and Avenue Capital, a hedge fund owned by a major Clinton donor. She had degrees from Stanford, Oxford and Columbia but had not quite found a way to harness all of her academic wherewithal.
To Mr. Band, who had remained loyal to Mr. Clinton when others abandoned him post-impeachment, and who was instrumental in building the Clinton Foundation from scratch, Ms. Clinton seemed like a dilettante.
In response to the scrutiny, Mr. Band wrote a 13-page memo outlining how he had raised many millions of dollars for the foundation from Teneo's corporate clients, including Coca-Cola and Dow Chemical, without taking a fee. In the memo, which WikiLeaks released this week, Mr. Band also described arranging tens of millions of dollars in income for Mr. Clinton in the form of lucrative speeches and consulting arrangements, some of them from foundation donors.
"We have solicited and obtained, as appropriate, in-kind services for the president and his family — for personal travel, hospitality, vacation and the like," Mr. Band wrote.
The subtext was clear: Where Ms. Clinton saw a messy overlapping of business and charity that could haunt both of her parents, Mr. Band saw an ungrateful daughter who was naïve about how what he called "Bill Clinton Inc." made its money, and how her own expensive lifestyle was funded.
"I just don't think any of this is right and that we should be treated this way when no one else is, only because CVC has nothing better to do and need justify her existence," he wrote in one email, using the initials for Chelsea Victoria Clinton. Mr. Band, who had already planned to leave the foundation to focus on Teneo, often expressed frustration at the global charity's nepotism, pointing to Ms. Clinton's installing her friends in central roles.
Mr. Clinton, who does not use email, is almost absent in the battles happening beneath him, mentioned only in passing as "Dad" or by his initials, "WJC."
In another email, Ms. Clinton alludes to her father's feelings about the tensions at his foundation. "Doug apparently kept telling my dad I was trying to push him out, take over — and Dad kept asking him — has she said that to you? To anyone? She's never said it to me," she wrote. Mr. Band has said the exchange Ms. Clinton describes never happened.
If the emails show Ms. Clinton getting a crash course on the cutthroat world on the periphery of the Clinton family, they also show a young woman deeply devoted to her parents and very much her mother's daughter.
Ms. Clinton often gravitated to weighty policy discussions and interspersed statistics and SAT words into casual conversations.
Hours after the 2012 attack on the United States mission in Benghazi, Libya, she mused about the unrest in Egypt and Libya in a late-night email to her mother. "Such anathema to us as Americans — and a painful reminder of how long it took modernism to take root in the U.S., after the Enlightenment, the 14th, 15th, 16th, 19th amendments," she wrote. "Much to discuss when we talk, hopefully tomorrow?"
In another email addressed to "Dad, Mom," Ms. Clinton seemed apologetic, writing, "I hope this mini-behemoth is not rife with grammatical errors or inadvertent gaps; I am sorry if either true."
Coming from a unwitting celebrity whose adolescence unfolded, often unkindly, in the public eye, Ms. Clinton's emails — which she usually sent under one of two aliases, Diane Reynolds or Anna James — also reflect her life in a rarefied world.
"So nice from the Bon Jovis," she wrote to her mother in 2013, forwarding well-wishes from the rock star and his wife after Hillary Clinton had been hospitalized.
Last year, a close aide to Mrs. Clinton, Huma Abedin, wrote in a message to John D. Podesta, the Clinton adviser whose email account was later hacked, that the Clintons' house in Chappaqua, N.Y., had to be cleaned after an employee had a stomach virus so that Mrs. Clinton could babysit for Chelsea's daughter, Charlotte.
"Sanitizing the house all day so the baby can be there," Ms. Abedin wrote. "WJC was out buying clorox wipes yesterday!"
Even when emailing with her parents, Ms. Clinton was not shy about delivering blistering criticism, as when she wrote to them after a trip to Haiti, which the foundation was trying to help rebuild after the devastating 2010 earthquake. "To say I was profoundly disturbed by what I saw — and didn't see — would be an understatement," Ms. Clinton wrote to her mother. "The incompetence is mind numbing."
And in rare instances, her emails contained an emotion that she never publicly shows: despair.
"I am sure there are three sides as my grandmother would say — his, hers and the truth," Ms. Clinton wrote to Mr. Podesta amid the foundation disputes. "All of it makes me very sad."
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