Don White, the first Cadillac Crew leader (1994-1997), authored the following history of the crew in January 2014. His narrative provides insights of where the Cadillac Crew's paradigm of working hard came from. The text below is adapted from a larger source archived here.
The Cadillac Crew formed accidentally; quite accidentally, actually. Following my two-year tenure as Supervisor of Trails, my successor, Andy Hiltz, asked me in January 1994 to continue and complete the A.T. relocation by Route 725 in Northern Virginia. I called some of my friends and PATC colleagues to help, and got to work on what turned out to be the coldest day of the year (in February, I believe). We did not get a lot done and what we did we had to re-do in the spring. So, I learned a lesson. As we kept going, I arranged for those who wanted to stay overnight to use what was then the Northern Virginia Trail Center (now removed). Some camped outside, some bunked inside. All made use of the shower and we grilled often on the concrete porch below or the deck above.
Phil Barringer, who served more than once as PATC president, was the overseer for the A.T. section from Route 55 to Manassas Gap Shelter, so this was his section. Phil, being somewhat elderly, did not come out and work with us. He kept calling me, though, about our progress - the new section involved a lot of sidehill, some turnpiking, and such.
As we kept working, more and more people joined us based on the ads I posted in the PA - I scheduled two trips per month. (Remember that the PATC was not online at that time.) As the core group jelled, some started talking about a name for what was becoming a crew (the Blue & White Team and South Mountaineers already existed, as did the Massarock and Shenandoah summer crews). My choice was "F Troop" and Tom Tamburo suggested "White's Wrecking Crew," amongst other purported "names."
About this time, Phil called me and asked if we would just open the trail by blazing it and come back later to do the side hill. (He was increasingly concerned about the advent of the "Thru-Hiker Season.") I assured him that we would be finished before that vaguely recognized season arrived, but he complained: "Don, you're building this to Cadillac standards!" I'd never heard this reference, ever.
In any case, when I told the crew this story, they started calling themselves The Cadillac Crew. No one in the crew owned or drove a Cadillac, however.