United CEO Scott Kirby and American CEO Robert Isom were once colleagues known as the ‘dream team.’ Now Kirby wants to acquire his rival

One takeover attempt is bold. Two? Rare indeed. But when news broke in mid-April that the United CEO was interested in acquiring his rival American Airlines, it was the third time this maverick air exec decided he wanted to reshape the playing field. As Fortune reported earlier, it’s far from clear such a merger would ever be approved, and on Friday American said it was “not engaged with or interested in any discussions regarding a merger with United Airlines.” Still, sources that spoke to Fortune called it “not impossible” given a President who “loves big deals.” And it’s worth looking back at Kirby’s track record to understand that, when he sees a deal, he is serious.

Put simply, Kirby has a long history of audacious ideas. It was back in the early 2000s that he rose at America West to become the top lieutenant to CEO Doug Parker. In 2005, the pair orchestrated the offensive that devoured much bigger U.S. Airways from Chapter 11. In 2007, American’s current CEO Robert Isom joined U.S, Airways—America West took its target’s name—as chief operating officer and served alongside CEO Parker........

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