4. Rich Hill, San Diego Padres
Rich Hill, commonly known as "Dick Mountain, was drafted three times before finally signing with the Chicago Cubs. Hill made his Cubs debut against the Arizona Diamondbacks on May 4, 2006. According to Baseball America, he was rated as having one of the best curveballs in the Cubs organization. His first major league victory wasn't until August 1, 2006, versus the Diamondbacks.
Fast forward to 2008, Hill was continuously experiencing command issues as well as back injuries. Following the season, Chicago had begun to look for a trade partner for Hill. In February of 2009, Hill was sent to the Baltimore Orioles for a player to be named later. Hill only made five starts in 2008, going 1-0 with a 4.12 ERA. Since leaving the Cubs, Hill's longest-tenured teams have been the Los Angeles Dodgers (2016-19) and the Boston Red Sox (2010-12, '15 and '22). In total, he has played for 13 franchises (in all six MLB Divisions) and is currently the oldest active MLB player.