By Ryan McGee
ESPN The Magazine

Updated: May 29, 2008, 1:33 PM ET

Everywhere Richard Childress goes, a motor pool of pickup trucks drafts behind him.

The 62-year-old NASCAR team owner is crisscrossing the mountainsides of the Grizzly Meadows Ranch, his 800-plus-acre spread in Montana, and he is supposed to be on vacation. But from the moment he arrived in the Yellowstone River Valley, he's been trudging up hills, cell phone in one hand, GPS device in the other.