Britain’s Sky News says that the companies have held “detailed negotiations” that are at an “advanced stage” for a deal that values the upstart news organization at $2.2B. One scenario would have Time Warner — which just spun off its magazine operation — meld its news channel HLN with Vice in return for about half of the combined company. If true, then it would give Time Warner a close relationship with a trendy digital media, TV, and publishing company that has captured the imaginations and financial support of former MTV chief Tom Freston, WME’s Ari Emanuel, WPP, and The Raine Group as well as comedian Bill Maher.

CEO Shane Smith founded Vice in 1994 as a music magazine; it now offers cutting edge news that critics say too often includes stunts. Supporters and critics feasted last year on Vice’s controversial effort to gain access to North Korea for its documentary series on HBO by arranging an exhibition basketball game featuring Chicago Bulls star Dennis Rodman and some members of the Harlem Globetrotters.

Last year News Corp (before it split into two companies) paid $70M for 5% of Vice, implying a value of $1.4B for the full company. Rupert Murdoch once tweeted that the company is a “wild, interesting effort to interest millennials who don’t watch or read established media.”