Brad Smith, Microsoft President and chief counsel, at Code 2018

David A. Grogan | CNBC

Brad Smith, President and Chief Legal Officer, Microsoft, speaks at the 2017 Cambridge Cyber Summit on October 4, 2017.

Tech history repeats itself, and nobody knows that better than Brad Smith, Microsoft’s president and chief counsel.

Smith was deeply involved in Microsoft’s antitrust battle against the federal government in the 1990s, and remembers how resolved the company was to fight it.

That turned out to be a mistake, Smith said at the Code Conference in Rancho Palos Verdes, California, on Tuesday.

“If we had worked things out in 1998, we might have been able to work them out before it became the antitrust version of nuclear war,” Smith said. Instead, the federal government tried to break up the company, a ruling that was eventually overturned on appeal.

Smith sees parallels at Facebook, which has come under recent scrutiny from the government over issues like Russian operatives using the platform to try and influence the 2016 presidential election and the Cambridge Analytica data leak.