Im not aware of webb's past, what exactly did he do to 'stray off the reservation', besides the now obvious running as a democrat.
Just a little background.
James Webb and Ollie North -- both who served in the Reagan Administration. There has a been a longstanding feud between the two of them dating all the way back to their days at the Naval Academy in the 1960s.
In 1967, North and Webb fought in a boxing match for the Bridge Championship (which is a big deal at the Naval Academy). Webb had been considered to be the better boxer but North won that fight on that day. Webb has held a grudge since that time.
During Iran Contra, Webb was the U.S. Secretary of the Navy. He issued various broadsides at North -- eventually forcing North to resign from the Marine Corps.
Fast forward to 1994. Oliver North ran for the U.S. Senate seat in Virginia against Chuck Robb. To the chagrin of many Republicans and former Reagan Administration officials, Webb endorsed Robb. The press had a field day with it.
In recent times, Webb has been a strong critic against the war in Iraq and to an extent on the war against terror. He does not favor an aggressive use of force in the Middle East. He has gone soft.
I have no idea where he stands on the broad array of issues. However, I sense that he is becoming a lot like Wes Clark -- a sellout on his earlier held beliefs.
"what did he do..."
Well the schlep ran a Kerry ad bashing Bush saying "Kerry has a plan" all along flashing images of Himself (Webb) with Reagan
He masquaraded as a "conservative" in the Reagan Admin fooling many back then well before being appointed SecNav. Nobody seemed to notice his liberal leanings, a shallowly veiled contempt for the Reaganites, and instead all were treated to his self aggrandizement on how much of a hero he was, echoes of Murtha and Kerry.
At the time, how could anyone accuse such a hero of being anything but a conservative? He fooled them and they were well placed and ranking people he took in.
He never was "on the reservation", simply a legend in his own mind.
When I would see the real Marines, humble heros for sure, I would wince at the sight of this pretender.