[1] Born in Redwood City, California, Caragher grew up with his mother in Morgan Hill after his parents divorced.

[2][3] Caragher played on the local Pop Warner football team and switched from running back to quarterback at age 12.

"[3] Attending Bellarmine College Preparatory in San Jose, Caragher lettered in three sports including football and graduated in 1985.

[4] At UCLA, Caragher redshirted his freshman year, then was backup quarterback from 1986 to 1989, including two seasons behind Troy Aikman.

In UCLA's 52–17 win on November 7, 1987, over Oregon State, Caragher was one of three backup quarterbacks who substituted for Aikman during garbage time.

[7] In the 1989 Cotton Bowl, senior Caragher took over on one handoff play after Aikman lost a contact lens.

[4] Succeeding Jim Harbaugh, Caragher became head coach at Football Championship Subdivision school University of San Diego in 2007.

[9] At San Diego, Caragher coached quarterback Josh Johnson, who was selected in the fifth round of the 2008 NFL draft.

Despite a 5–7 regular season record, San Jose State was bowl-eligible due to a lack of 6–6 or better teams for all available bowl game spots.

[14] In 2018, Caragher became offensive quality control coach and on-campus recruiting coordinator at San Diego State under Rocky Long.