Happy Wednesday, and welcome back to Dry Powder.

At the age of 63, Brian Roberts likely has another decade or so at the helm of Comcast before he decides to hang up his cleats. Roberts, of course, is an inveterate dealmaker, and the odds that he sits on the sidelines while his competitors hunt large M&A game is slim to none. As fate would have it, a possible mega-deal might already be coming into view. In today’s issue, I look at how Roberts’s past might foreshadow the media deal of the century, and consult with cable pioneer Tom Rogers about the strategic considerations likely running through his mind.

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There was the landmark $72 billion acquisition, in 2001, of AT&T Broadband, the phone company’s cable business, at the time one of the largest M&A deals in history. It was an audacious and, at first, unfriendly deal, especially since AT&T Broadband was a subsidiary of AT&T and most decidedly not for sale when Roberts approached Michael Armstrong about buying the business. In the end, Roberts wore Armstrong down and put pressure on the AT&T management and board of directors to sell him the business by making public his generous offer for the subsidiary. (Along with many others, I worked on the deal as a M&A banker when I was at JPMorgan Chase.)...