Former Senator Jim Webb, whom I've considered a friend since the late 1970s, is about the most independent-minded person I've ever met. That is part of what makes his writing so distinctive and sharp. Thus it seems natural, almost fated, rather than disorienting or disturbing that he would contemplate an independent run for president, rather than continuing as a Democrat.
Webb's most consistent message—as a writer, in the Senate, during his recent campaign—has involved duty, loyalty, and the respect owed to those who serve. In the Senate, he was also a very early champion of the cause of decarceration and criminal justice reform. If you wanted an antidote to what I have called Chickenhawk Nation—a country always at war, most of whose citizens are untouched by war—you would find it in the Webb family. Many of its members have fought and thus are careful rather than cavalier about the causes for which they would send others to fight.
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Jim Webb, Webb Campaign Press Release - Jim Webb, Independent Online by Gerhard Peters and John T. Woolley, The American Presidency Project https://www.presidency.ucsb.edu/node/313011