 He spent four seasons in the Royals' organization, also coaching with the Carolina League's Wilmington Blue Rocks, the Northwest League's Eugene Emeralds and the Midwest League's Springfield Sultans.After this, Santana worked three seasons in the Boston Red Sox organization, overseeing the Red Sox Dominican program in and as a roving infield instructor and hitting coach with the Class A New York–Penn League Lowell Spinners in and before moving on to the White Sox.He spent four seasons as the ChiSox's minor league infield instructor before being promoted to the major league club in the same capacity while also serving as their first base coach for and .