There are plenty of ways to describe WikiLeaks’ role as a potential spoiler in the presidential race. Watching Julian Assange beam in to talk with Sean Hannity and tease election surprises to come, you might call it sinister, radically transparent, or damning but still compromised depending on your politics.

Whatever happens in October, just don’t call it a surprise.

Since 2012 Assange, WikiLeaks’ founder and leader, has been confined to the Ecuadorian embassy in London fighting extradition to Sweden on sexual-assault charges. The inner workings of WikiLeaks—effectively a one-man operation even before its leader’s isolation—can be opaque. In some matters Assange has maintained WikiLeaks’ secrets but he has also made certain positions perfectly clear over the years: his loathing for Hillary Clinton, his increasing alignment with the Russian government’s positions, and his interest in electoral politics.

Assange’s antipathy for Clinton is well established and seems to be a hatred he came to honestly. It’s a view hardly unique to Assange that sees the former Secretary of State as uniquely corrupt and bellicose even among her peers.

Back in 2010 Assange suggested Clinton should resign after his organization leaked diplomatic cables that showed her sanctioning spying on foreign diplomats.

Assange wasn’t the only one to call for Clinton to step down in the wake of “cablegate,” some respected American journalists did as well, but his assertion that at WikiLeaks “we don’t have targets” made in the same interview where he called for her resignation just doesn’t hold up. Clinton has been a repeated target of both WikiLeaks and Assange himself. In his book When Google Met WikiLeaks, Assange detailed the Clinton State Department’s questionable collusion with Google. And there are clear signs that WikiLeaks’ dump of nearly 20,000 hacked emails taken from the Democratic National Committee was timed to do maximum damage to Hillary Clinton’s presidential campaign. Additionally, both U.S. officials and private cybersecurity experts have pointed to the Russian government’s likely involvement in hacking the DNC emails.

In a statement posted to WikiLeaks’ Twitter account and in interviews, Assange has responded to the charge of Russian co-option. Clinton, according to Assange, “palled up with the neocons responsible for the Iraq War and she’s grabbed on to this sort of neo-McCarthyist hysteria about Russia, and is using that to demonize the Trump campaign.”

Even given WikiLeaks apparent Russian connections, and the Clinton campaign’s attempts to amplify them, the emails raise serious questions about Clinton’s staff granting political favors to donors and the DNC’s efforts to sabotage Bernie Sanders’s campaign. DNC Chair Debbie Wasserman Schultz resigned in the ensuing scandal and, more than a month later, the leaks are still generating negative press for Clinton and keeping a spotlight on WikiLeaks.

As Assange and his allies now tease WikiLeaks’ next leak, it’s worth noting just how long he has been building up to this “October surprise.”

The first public mention of WikiLeaks’ plans for Clinton White House ambitions appears to have come from an unlikely source. The 6-foot-7 Kim Dotcom was born Kim Schmitz in West Germany.

By 2005, he had been arrested multiple times when he legally changed his surname to “Dotcom.” The new name was an “ homage to the technology that made him a millionaire,” The Wall Street Journal reported in 2012 in a story on his arrest in New Zealand. Dotcom remains in New Zealand today where he’s fighting extradition to the U.S. on charges related to alleged copyright infringement, racketeering, wire fraud, and money laundering by his the file-sharing service Megaupload.

Dotcom and Assange cemented a political alliance in 2014 when the two of them plus journalist Glenn Greenwald and famed leaker Edward Snowden formed “the all-stars of the internet freedom movement,” as The Daily Beast’s Lennox Samuels dubbed them at the time. Greenwald flew to Australia while Assange and Snowden were beamed in on behalf of Dotcom’s Internet Mana Party. Their big revelation in the race was a leak from the Snowden archives related to New Zealand’s surveillance program, released just in time for that country’s national elections.

Greenwald maintained that he favored no party in the elections and had only come to New Zealand to testify as a surveillance expert. For Assange the connection with Dotcom was not just about the shared ideology of two digital natives. Information was not the only thing the two of them were trying to free. “We share the same prosecutor, so I understand what is going on there,” Assange said, explaining his connection to Dotcom. America, he added, “is trying to apply U.S. law in as many countries as possible, applying their law in New Zealand to coerce and pluck out people to other states.”

While Dotcom’s extradition hearing is happening now (he’s been promoting its livestream on Google-owned YouTube), Assange has remained inside the Ecuadorian embassy for fear of being criminally charged in the United States for various leaks of American secrets, including many cables from Hillary Clinton’s State Department. That leak, in hindsight, foreshadowed many of the concerns playing out in this election about email hacks, exposed secrets and even Clinton’s use of private email servers while she was Secretary of State.

Assange’s foray into New Zealand’s election received little attention at the time and, to no one’s great surprise, Dotcom’s party lost its bid. In retrospect it was a significant development, and another entry into electoral politics after losing a remote run in 2013 for a seat in Australia’s Senate under his own WikiLeaks party.

Fast-forward to December 2014. The race hadn’t quite begun but the presidential campaigns of established candidates like Hillary Clinton were already rolling and gathering force when Dotcom tweeted that he would be Clinton’s “worst nightmare.”

The tweet didn’t cause much stir but came up again in May 2015 when a Bloomberg News interviewer asked about it. “Well, I have to say it’s probably more Julian but I’m aware of some of the things that are going to be roadblocks for her,” Dotcom said, adding when pressed that Assange “has information.”

In a political campaign there are always more secrets than public attention and Dotcom with his legal troubles and his strong resemblance to a Bond villain from central casting was largely ignored at the time. It wasn’t until June of this year, a month before the Democratic primaries, when Assange told an ITV interviewer, “We have upcoming leaks in relation to Hillary Clinton,” and Dotcom’s tweet suddenly looked less like a wish than an insider’s tip.

All of which led to the first round of leaks, the ones we’re still talking about now, which came out just days before the Democratic Convention in July, and which Assange suggests may have been only the lead-up to his grand finale.

Shortly after resigning from Donald Trump’s presidential campaign, while continuing to advise Trump himself, longtime Republican operative and self-described “political hitman” Roger Stone said that he had been in touch with WikiLeaks. “I actually have communicated with Assange,” Stone told a Republican organization. “I believe the next tranche of his documents pertain to the Clinton Foundation, but there’s no telling what the October surprise may be.”

Assange still presents himself as above the fray, more interested in liberating secrets and destroying the barriers to information than in grubby power exchanges of partisan politics. But at this point, even confined to a diplomatic building in London, he has considerable experience in influencing elections abroad and a documented political record.

If he insists that the choice between Clinton and Trump amounts to asking, “Do I prefer cholera or gonorrhea?” it’s not because he is too pure to have made his choice.