I suppose you could call Air America a failure, and from a business perspective it certainly was. It never operated in the black, and seemed to be in the midst of financial and management turmoil since before it launched in April of 2004.
But it helped catapult Al Franken into the U.S. Senate, and launched a then unknown Rachel Maddow on the path toward her own show on MSNBC, and will leave behind dozens of thriving progressive talk stations nationwide. And without the ecosystem that Air America spawned, Ed Schultz and other successful progressive talkers might never have had the opportunity to reach a national audience.
And Air America was also the platform from its Portland affiliate, progressive talk radio station KPOJ was launched and continues to thrive.
I wrote at the time that Air America went live that the question would be this: Is the dreadfully self-pleased know-nothingism of conservative talk radio--and at that point, conservative talk radio was nearly all there was--a function of conservatism as it now exists, or of talk radio? If it's the latter, the pressing need for an Air America wasn't too clear to me.
And yes, Air America programming has had its drudges over the years, but for every Bill Press, cheerfully steering the conversation toward the beltway truism of the week, there were Franken, Rhodes, Seder, and Maddow. (Although, for mixed reasons, only Maddow remained part of Air America's line-up at the end.)