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December 1, 2021

Salesforce (CRM.N) once considered acquiring Twitter (TWTR.N); now it has promoted its president, Bret Taylor, to the role of co-chief executive the day after he took the job as chairman at the social-networking mainstay, announced as part of leader Jack Dorsey’s exit. The moves re-introduce a messy situation.

Salesforce wanted to acquire Twitter in 2016, according to Reuters at the time. Instead, investors balked, and founder and CEO Marc Benioff backed away. It was not the only M&A frustration for the entrepreneur, who is famous for his attempts at empire-building. He lost a $26 billion bidding war for LinkedIn to Microsoft (MSFT.O) the same year.

Still, Benioff’s status as a prolific acquirer, as further evidenced by a leaked presentation showing a vast range of targets he considered, makes Taylor’s elevation at Twitter an uncomfortable one. Dorsey’s tenure was dogged by criticism over his dual roles at Twitter and as chief executive of fintech company Square (SQ.N).

With its executive reshuffle, Twitter may have just traded one conflict for another: an absentee CEO leaves, and the co-CEO of a one-time suitor steps in to lead the board.