I am real glad that don't work at that place -- if this is an example of the planning, foresight and intelligence of their management, they are probably making other errors in judgment as well. And I am also happy to report that I have never worked at a place where a manager would propose something like that -- and especially not where a manager would be pushing people into doing it.
I would say: if he wants to try it, Fine -- go for it. And, if anybody wants to go with him, then fine, go with him.
I would offer to drive along behind and pick up the stragglers -- but each person I picked up would have his choice of paying $25 to my favorite charity (the Red Cross) or owe me a lunch -- whatever he chose.