after graduation, olney began covering baseball in 1989, as the "nashville banner"<nowiki>'</nowiki>s beat reporter assigned to the triple-a nashville sounds. while in nashville, he formed a close relationship with the legendary don meyer, head coach of the men's basketball program at david lipscomb university. he later worked at the "san diego union-tribune" and "baltimore sun". he arrived at the "times" in 1997 and in his first year won an associated press award.