Cheryl Contee, thirty-eight, is the founder of the blog Jack & Jill Politics: A black bourgeoisie perspective on U.S. politics. She grew up with Ebony and Jet, but has a hard time remembering the last time she’s read an issue. Ebony, she says, has not updated its style or its use of the Web sufficiently to fit modern African Americans. “I think they’re trying to catch up,’’ she says. “The question is whether they have time.’’

Contee believes that while race still matters, it does not matter nearly as much as it did even a few years ago. “My experience in America is very different than the lives of my parents and grandparents,’’ she says. “If it weren’t for the increasing assimilation of African Americans into society, then there wouldn’t be a black president. I don’t know if Ebony and Jet necessarily acknowledge that reality.’’

Yet she says she started Jack and Jill Politics in 2006 because when she surveyed the Internet she did not “find the voice of the African-American middle class being respected and honored in any significant way.’’

Of course, that’s the same reason John H. Johnson started Ebony in the 1940s.

Veteran journalist Sylvester Monroe thought he had found his dream job when he joined Ebony as a senior editor in 2006. He had been a journalist for thirty-seven years, twenty-seven of them at Time and Newsweek. Monroe was lured to the magazine by the publisher’s promise that Ebony was going to be different. It was going to make a splash on the Internet and improve the writing in its print publications. “I was told we were going to bring Ebony into the twenty-first century,’’ he says, “that we were going to make it more relevant, give it some edge, bring it back to its old position as a relevant and important publication.’’

Monroe had visions of a combination of Ebony, Vanity Fair, and Emerge, the formerly hard-hitting but now defunct black monthly that once put an image of Supreme Court Justice Clarence Thomas on the cover made up to look like a lawn jockey. “It could have been the best job I ever had,” Monroe says. “But almost as soon as I got there, things went south.’’

Advertising revenues plummeted across the industry, and Ebony put its grand ambitions on the back burner. Monroe hung on for as long as he could, thinking once the economy turned around the job of remaking Ebony would resume.

One day in 2007, more than a dozen members of Ebony’s editorial staff were seated around a gleaming table in the eighth-floor conference room, debating who should be included in the list of the twenty-five “coolest’’ black men of all time. Monroe, who is in his late fifties, and others nominated such notables as Muhammad Ali, Denzel Washington, and Billy Dee Williams. The twenty- and thirty-something staffers rolled their eyes. “Can’t we have someone under fifty?’’ they pleaded.

Monroe says there was a generational tension between old and new over Ebony’s future both inside and outside of the magazine. “Linda Johnson-Rice,’’ he says, “was always very concerned about walking the fine line between bringing in new readers and not alienating its traditional base.’’

Monroe quit last year, “frustrated out of my mind’’ over a lack of money for writers and a coherent editorial direction. If Ebony gives up as well, Monroe says, “My generation will be saddened and will miss it. People under fifty probably won’t miss it at all. They feel Ebony has served its purpose.’’

Don Terry is a 2009-2010 Encore Fellow at CJR. He has worked at the Chicago Defender, the Chicago Tribune, the St. Paul Pioneer Press, the St. Paul Dispatch, and The New York Times, where he was part of the team that won the Pulitzer Prize in 2001 for the series "How Race is Lived in America."