Known primarily as a reserved figure, Holliday has played for years in the shadows of such franchise icons as Todd Helton and Albert Pujols, which accommodated his demeanor well. However, he has emerged as a veteran presence for the Cardinals willing to assist and entertain younger players and top prospects as they attempt to adjust to a lifestyle of playing baseball. In January 2012, he invited Matt Adams, Ryan Jackson, Charlie Tilson and Kolten Wong for a weeklong stay in St. Louis at the tony Frontenac Hotel. Activities included eating out, hitting, working out and attending a St. Louis Blues game. Holliday also became more active on his Twitter account and more readily availed himself as a guest on talk radio shows. Further, he befriended former teammate David Freese, who, shortly after Holliday's arrival in St. Louis in 2009, was arrested for driving under the influence. However, after becoming daily workout partners and socializing, teammates noted a "positive influence" on Freese.