In addition to his presence as a leader on the field, Holliday is active in charity work and assisting his teammates off the field. Thus, the St. Louis chapter of the Baseball Writers' Association of America has awarded him the Darryl Kile Good Guy Award. He is a frequent visitor to children's hospitals. From 2012 to 2016, Holliday co-sponsored a pledge drive for Greater St. Louis hospitals called "Homers for Health," which raised more than $3.7 million. Because of his hitting abilities and strength, he has sometimes been called the "Stillwater Stinger".