© REUTERSJohn Podesta aboard 'Hill Force One', the nickname for Clinton's campaign plane
The anti-secrecy website says it will release tens of thousands more emails between now and election day.
Clinton campaign chairman John Podesta, whose emails were hacked, has claimed the Russian government was behind the leak and the Trump campaign knew about it in advance.
He has refused to confirm or deny the emails' authenticity, suggesting some could have been doctored, without so far pinpointing any of the correspondence as fake.
These messages are different from the other Clinton email controversy, when she was found to have and broken government rules by exclusively operating a private server from her upstate New York home while secretary of state.
So what has the Wikileaks dump told us?
© GETTY IMAGESDoug Band and John Podesta leave the oval office on Bill Clinton's last day as president
In a 12-page memo written by Doug Band, a longtime aide to Bill Clinton, he describes using his consulting firm to raise money for the Clinton Global Initiative as well as direct personal income for the former president.
Mr Band rallied clients of his firm, Teneo, to contribute directly to Mr Clinton for "in-kind services for the President and his family - for personal travel, hospitality, vacation and the like" referring to that fund as "Bill Clinton Inc".
Several companies directly paid the former president for his speeches or advice, as well as making contributions to the Clinton Global Initiative. Republicans have criticised this, saying it allowed corporations to pay for access to the former president.
One client, Coca Cola, received a face-to-face meeting with the former president at his home in 2009, after contributing millions to the non-profit foundation.
Donald Trump tweeted a link to the Washington Post article about this with his anti-corruption mantra #DrainTheSwamp
© GETTY IMAGESJohn Podesta, Neera Tanden, and Hillary Clinton
On the same day that news of a private email server broke, John Podesta, who later became her campaign chairman, emailed Neera Tanden, who worked for the Clinton campaign in 2008 and has remained a close adviser, to complain about Mrs Clinton's "instincts".
"We've taken on a lot of water that won't be easy to pump out of the boat", he wrote in September 2015 as Clinton staff feared that Vice President Joe Biden would join the Democratic primary race.
"Most of that has to do with terrible decisions made pre-campaign, but a lot has to do with her instincts," he wrote, to which Mrs Tanden responded "Almost no one knows better [than] me that her instincts can be terrible."
In the email exchange, Mr Podesta also complained that Clinton's personal lawyer David Kendall, and former State Department staffers Cheryl Mills and Philippe Reines "sure weren't forthcoming here on the facts here". Mrs Tanden responds "Why didn't' they get this stuff out like 18 months ago? So crazy."
She later answered her own question saying, "I guess I know the answer. They wanted to get away with it."
What Obama knew about Clinton private email
When President Barack Obama told an interviewer that he first learned of Mrs Clinton's private email server at the "same time everybody else learned it, through news reports", the Clinton campaign emailed each other to say that the president was not telling the truth.
The evening after the interview aired Clinton spokesman Josh Schwerin emailed to say "it looks like POTUS just said he found out HRC was using her personal email when he saw it in the news".
"We need to clean this up", Clinton's former chief of staff Cheryl Mills responds.
"He has emails from her - they do not say state.gov", she wrote, implying that Mr Obama was aware that Clinton was using a private email server rather than her State Department-issued email account.
White House spokesman Josh Earnest later clarified to say that the president had exchanged emails with Clinton but that he "was not aware of the details of how that email address and that server had been set up".
Morocco 'quid pro quo'
Mrs Clinton's aide Huma Abedin, usually known for her unflinching loyalty, was blunt in her criticism of her boss over a Clinton Foundation summit in Morocco.
At the time of the meeting in Marrakesh, in May 2015, Mrs Clinton was no longer secretary of state but about to announce her campaign for president. But four months before it took place, Abedin voiced concern about her pulling out. "If HRC was not part of it, meeting was a non-starter," she warned. "She created this mess and she knows it."
The implication from the leaked emails is that a $12m donation from the king of Morocco was dependent on Mrs Clinton attending the summit.
"Her presence was a condition for the Moroccans to proceed so there is no going back on this," Abedin wrote to campaign manager Robbie Mook in a November 2014 email.
In the end, Mrs Clinton decided not to attend and sent husband Bill and daughter Chelsea instead. There is no record of a $12m donation.
Mr Mook on Sunday said there was no evidence of wrongdoing or "quid pro quo", and that his emails with Abedin showed he simply did not want any scheduling distractions for Mrs Clinton.
Sanders is a 'doofus'
In December 2015, Mr Podesta attacked Mrs Clinton's primary election rival Bernie Sanders for criticising the Paris climate change agreement.
"Can you believe that doofus Bernie attacked it?" said Mr Podesta.
When asked on CNN about it, Mr Podesta admitted he was frustrated at the time but he had a very good relationship with the Vermont senator.
Bill Gates for veep?
Mrs Clinton's campaign considered Microsoft co-founder Bill Gates or his wife Melinda as her running mate, according to the hacked emails.
Mr Podesta drafted a list of nearly 40 names for her potential vice-presidential pick, organising it by what he called "rough food groups", which appeared to refer to demographic coalitions.
The list included Hispanic, white and black men, three former high-ranking military officers, business leaders and female senators.
Among those included were Apple's Tim Cook, former New York Mayor Michael Bloomberg, General Motors' Marry Barra and Starbucks chief executive Howard Schultz.
Senator Bernie Sanders was listed in a group by himself.
'Clintons won't forget'
The Clinton campaign tried to reschedule the Illinois presidential primary to a month later, so as to make it less likely that a moderate Republican would get a boost following the Super Tuesday primaries.
"The Clintons won't forget what their friends have done for them," future Clinton campaign manager Robby Mook wrote in the November 2014 email to Mr Podesta.
But Mr Mook said the vote would be difficult to reschedule because Illinois Democrats "feel forgotten and neglected by POTUS", a reference to President Obama.
The primary was ultimately held on its original date, 15 March this year.
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Comment: These examples are just the tip of the iceberg.