No he didn’t. People will often claim there are Twitter direct messages (DMs) of Assange and the right-wing serial liar Roger Stone scheming together in the lead-up to the 2016 election, but the only DMs between Stone and the @WikiLeaks account (presumed but not proven to be Assange) from that time period are WikiLeaks telling Stone to stop falsely claiming that the two have been talking.
Stone had been publicly boasting of having a WikiLeaks back channel (a claim the alleged back channel Randy Credico has always rejected), and when WikiLeaks publicly denied this Stone angrily messaged their Twitter account.
From The Atlantic, where the leaked DMs between Stone and WikiLeaks were first published:
On the afternoon of October 13, 2016, Stone sent WikiLeaks a private Twitter message. “Since I was all over national TV, cable and print defending wikileaks and assange against the claim that you are Russian agents and debunking the false charges of sexual assault as trumped up bs you may want to rexamine the strategy of attacking me- cordially R.”
WikiLeaks — whose Twitter account is run “by a rotating staff,” according to Assange — replied an hour later: “We appreciate that. However, the false claims of association are being used by the democrats to undermine the impact of our publications. Don’t go there if you don’t want us to correct you.”
That’s the only record of any communication between Stone and WikiLeaks prior to the 2016 election: a square refutation of the claim that Stone conspired with WikiLeaks.