A military veteran and former Senator himself, Webb likely could not overlook the decision by Hillary Clinton to ignore the repeated calls for extra security by Ambassador Stevens in Libya weeks before the fatal attack on the consulate in Benghazi.
Hillary admitted error in the attack during investigation proceedings led by Senator Rand Paul and Trey Gowdy, but brushes off calls to be held accountable or step down, citing that security analysts were to blame for the failure of security.
Jim Webb is certainly not the first Democrat to endorse Trump; reportedly hundreds of thousands of blue collar democrats poll in favor of the Donald. But he is certainly the highest profile Democratic pol to come out with an endorsement of Trump over Hillary.
Webb was born in Saint Joseph, Missouri, to James Henry Webb, Sr., and his wife, Vera Lorraine (Hodges). As the second of four children and the older son, he grew up in a military family, moving frequently as his father’s career in the United States Air Force required. The family crisscrossed the country, living in Missouri, Illinois, Texas, Alabama, Nebraska, California, and Virginia, as well as in England, where his father was an exchange officer with the Royal Air Force.
Webb was commissioned as a second lieutenant in the U.S. Marine Corps. Attending the Marine Corps Officer Basic School shortly after leaving Annapolis, he graduated first in his class. He was promoted to first lieutenant in the second half of his tour in Vietnam. He served as a platoon commander with Delta Company, 1st Battalion 5th Marines. He was awarded the Navy Cross for heroism in Vietnam, the second highest decoration in the Navy and Marine Corps. Webb also was awarded the Silver Star, two Bronze Stars, and two Purple Hearts.
After returning from Vietnam, he was assigned to Marine Corps Base Quantico, Virginia, as an instructor for Officer Candidates School (OCS). Deep selected for Captain, he was then assigned to the Secretary of the Navy’s office for the remainder of his active duty. His war wounds left him with shrapnel in his knee, kidney, and head. The injury to his knee led to a medical board that decided on medical retirement.
In a 1990 New York Times opinion piece, Webb opposed further U.S. military escalation in Saudi Arabia during Operation Desert Shield citing lack of a coherent strategy and consent from the United States Congress. He also warned against a permanent military presence in the Middle East.
During the 2004 presidential campaign, Webb wrote an op-ed piece for USA Today in which he, as a military veteran, evaluated the candidacies of John Kerry and George W. Bush. He criticized Kerry for the nature of his opposition to the Vietnam War in the 1970s while affiliated with the Vietnam Veterans Against the War, and accused Bush of using his father’s connections to avoid service in Vietnam. Webb wrote that Bush had “committed the greatest strategic blunder in modern memory” with the 2003 invasion of Iraq.