After a season with Chicago (split between AAA and the big league club), Cairo caught the eye of the Cardinals' Tony LaRussa. The Cubs placed Cairo on Waivers and the Cardinals snapped him up in time for the 2001 post season run. Cairo would pick up a hit and a stolen base against the eventual World Series Champion Diamondbacks in the 2001 NLDS. The following year, Cairo would play all over the diamond, appearing at every position except pitcher, center field, and catcher. He filled the Super Utility role that was a vintage LaRussa strategy. He would give anyone and everyone a day off when called upon, and was a valuable double switch option in the National League.
In the 2002 NLDS, Cairo reached base in all 5 plate appearances. He'd add 5 more hits in the NLCS, but the Cardinals fell just short, losing to the GiantsCairo had a great season with the Yankees in 2004, again playing all over the infield. He appeared in a career high 122 games, and topped 100 hits for the first time since his days as an everyday player in Tampa. He would go on to play for the Mets, then back to the Yankees, then the Cardinals again, then Seattle and Philadelphia before finally settling for a 3 year stint in Cincinnati. His time with Philly included his only World Series experience, though he was on the roster he did not get a plate appearance. In all, Cairo played in 17 MLB seasons, and collected over 1,000 career hits and scored over 500 career runs.
This year Cairo has re-united with Tony LaRussa to serve as the bench coach for the Chicago White Sox.