Skip Schumaker played for the Cardinals from 2005-2012. He was a part of the 2006 (did not actually play, however) and 2011 World Series teams, and he played a solid second base for both teams. He was never an All-Star, but he grinded out innings and was serviceable offensively for most of his career.
Since his retirement in 2015, Schumaker has served various roles for MLB teams. His first non-playing job was as an assistant to baseball operations and player development for the San Diego Padres. He held this position until the end of the 2017 season. In 2018, he became the Padres' first base coach until the end of the 2019 season. Eventually, Skip was let go of his role with the Padres, and he joined the Cardinals as their bench coach in 2022. The Cardinals went 93-69 that year, and they lost to the Phillies in the Wild Card round.
After 2022, the Miami Marlins hired Skip as their manager, and he never looked back. Schumaker led the Marlins to their first playoff appearance since 2020 in the COVID season. Before that, the last time they made it to the playoffs was in 2003 when they won the World Series. Despite the Marlins losing in the Wild Card round this year, the fact that they even made the playoffs in a tough division like the National League East speaks volumes to Schumaker's ability to motivate a team.
Randy Flores played in the majors from 2002-2010. In 350 games (3 starts), Flores had a 4.61 ERA, 1.584 WHIP, and 4.45 FIP. He played 5 seasons with the Cardinals ('04-'08) and was a decent reliever in those years.
Flores has been most effective for the franchise in a front-office capacity for the Cardinals. Randy retired from baseball in 2010, and he worked with various schools in the Pac-12 as a coach and analyst for ESPN. He was brought on as the Director of Scouting in 2015 in St. Louis, a position that allowed him to oversee all aspects of the scouting department and amateur draft.
In 2018, Flores was promoted to Assistant General Manager. He has been a fantastic drafter for the Cardinals, and he looks to be primed to take over a General Manager role soon for a team. Flores has recently grown in the national spotlight as a potential President of Baseball Operations for various teams, and it's possible he will leave the organization soon if the team doesn't find a spot for the talented Assistant GM.
A.J. Pierzynski had a long career in the majors. He played for 7 teams in 19 years. Pierzynski was the backup catcher to Yadier Molina in the second half of 2014, and he provided great veteran leadership in the clubhouse. Despite a short career in St. Louis, A.J. still left his mark on the town. He was able to fill in for the injured Yadier Molina in the 2014 playoffs, and he had strong connections with the starters while also providing timely offense.
Since his retirement, Pierzynski has dabbled in the broadcast booth, but he is most known for his podcast, Foul Territory. With Todd Frazier, Adam Jones, Lorenzo Cain, Brock Holt, and Jason Kipnis, Pierzynski discusses various baseball topics in an unfiltered way. It is a fun, light-hearted, intelligent podcast that provides great insight into the baseball world through the eyes and ears of former All Starts. Pierzynski has seen ample success off the field since his retirement.