Twice named first-team all state, Cockrell led Joplin, Missouri's Parkwood High School Bears football team to a 31–3 record during his three years as starting quarterback.

That team has recently been inducted into the Joplin Area Sports Hall of Fame, alongside the likes of NASCAR's Jamie McMurray.

[9] The San Francisco Giants made Cockrell the ninth pick overall in the 1984 MLB draft, and he chose to forgo his senior year in college and play professional baseball.

He debuted for the Colorado Rockies on September 7, 1996, with a pinch hit appearance in which he struck out against All-Star closer and future National Baseball Hall of Fame member Billy Wagner.

[13] His leadership skills and teaching ability, though, shone through and Cockrell spent the next few years working as a manager and hitting coach in various parts of the Colorado Rockies' development system.

Under Cockrell's guidance in 2007, the Rockies slugged their way to a National League Championship, leading the circuit in batting, on-base percentage, and total hits.