Below is a timeline breaking it all down.
Sept. 20, 2016: WikiLeaks sends its first direct messages to Trump Jr., sharing a password it discovered for a new anti-Trump PAC's website, putintrump.org.
Sept. 21: Trump Jr. responds by saying, “Off the record I don't know who that is but I'll ask around. Thanks.”
Oct. 3: WikiLeaks inquires about getting the Trump campaign's help to push a story about Hillary Clinton allegedly suggesting that WikiLeaks founder Julian Assange should be droned. Trump Jr. says the campaign “already did that earlier today.” He then asks about a rumored “Wednesday leak I keep reading about.” WikiLeaks doesn't respond.
Oct. 12 8:31 a.m.: WikiLeaks suggests Trump Jr. promote its leaked Democratic documents: “Hey Donald, great to see you and your dad talking about our publications. Strongly suggest your dad tweets this link if he mentions us wlsearch.tk.” WikiLeaks suggests tweeting the link will get Trump supporters to dig through the hacked emails to find things the media had missed.
Oct. 14 morning: Pence denies the campaign is working with WikiLeaks.
Fox News host Steve Doocy: “Some have suggested on the left that it's all this bad stuff about Hillary, nothing bad about Trump — that your campaign is in cahoots with WikiLeaks.”
Pence: “Nothing could be further from the truth. All of us have had concerns about WikiLeaks over the years, and it's just a reality of American life today and of life in the wider world.”
(Note: The web address in this tweet is identical to the one WikiLeaks recommended two days earlier, including the lack of an “http://")
It's worth noting here that Trump had been talking about WikiLeaks even shortly before his Oct. 12 tweet. Here's what he tweeted just the day before:
WikiLeaks's Oct. 12 message to Trump Jr. also noted how the candidate had been talking about it (“great to see you and your dad talking about our publications"). So it's possible the juxtaposition of Trump Sr.'s Oct. 12 tweet and the WikiLeaks message to Trump Jr. is just a coincidence. But if you look at what Trump Jr. tweeted two days later, it's basically precisely what WikiLeaks had suggested.
It's worth noting that in other cases, Trump Jr. didn't respond to WikiLeaks or didn't take its advice. For example, WikiLeaks at one point suggested the Trump campaign leak “one or more” of Trump's tax returns. But at the very least, Trump Jr. exchanged messages talking about campaign strategy with WikiLeaks, which has been linked to the Russian government and which American intelligence says was used to disseminate emails hacked by Russia. Trump Jr. clearly asks for inside information about leaks that might be coming from WikiLeaks.
The other big question here, beyond the Trump campaign appearing to coordinate with an alleged cut-out for the Kremlin, is Pence's denial. It is complete and unmistakable, and it has now been directly contradicted. The whole thing harks back to when Pence wrongly denied that Michael Flynn had discussed sanctions with Russia's ambassador after the 2016 election. Yet again, Pence offered a blanket denial that he shouldn't have.
The totality of the messages yet again call into serious question the Trump campaign and White House's denials of coordination with unsavory characters and even, by extension, Russia. And unlike that June 2016 meeting with a Russian lawyer, in this case this coordination appeared to lead to a specific strategic action. The question from there is how directly WikiLeaks is linked to the Russian government.
Correction: The timing of the tweet above from President Trump has been corrected from 9:46 a.m. to 8:46 a.m.