Kevin Gregg's journey through Major League Baseball is a testament to perseverance and adaptability. Born on June 20, 1978, in Corvallis, Oregon, Gregg attended Corban University, where he honed his skills on the mound. His professional career began when he was drafted by the Oakland Athletics in the 15th round of the 1996 MLB Draft. However, it wasn't until several years later that he would make his debut in the major leagues.

Gregg's MLB debut came with the Anaheim Angels in 2003. Initially, he served as a middle reliever, a role that allowed him to demonstrate his capabilities. His time with the Angels was marked by steady improvement, and he became a reliable option out of the bullpen. In 2004, he was part of the Angels' roster that competed in the postseason, gaining valuable experience on a larger stage.

In 2006, Gregg was traded to the Florida Marlins, where he transitioned into a more prominent role. The Marlins utilized him as a closer, and he responded by recording 32 saves in the 2007 season. This performance solidified his reputation as a dependable closer, and he continued to serve in this capacity for the Marlins through the 2008 season.

Gregg's career took another turn when he signed with the Chicago Cubs in 2009. During his tenure with the Cubs, he continued to close games, adding 23 saves to his career total. Despite some challenges, including a high number of blown saves, Gregg remained a fixture in the bullpen.

The Toronto Blue Jays acquired Gregg in 2010, and he once again assumed the role of closer. That season, he achieved 37 saves, a career-high, and became a key component of the Blue Jays' bullpen. His performance earned him a contract extension, but he opted for free agency after the season.

In 2011, Gregg joined the Baltimore Orioles, where he spent two seasons. While his time with the Orioles was marked by inconsistency, he provided veteran leadership to a young bullpen. Gregg's role shifted from closer to setup man, reflecting the evolving nature of his career.

Gregg returned to the Cubs in 2013, where he experienced a resurgence. He reclaimed the closer role and recorded 33 saves, proving that he still had the ability to perform at a high level. His performance that season was a bright spot for the Cubs, who were in the midst of a rebuilding phase.

The latter part of Gregg's career saw him sign with the Miami Marlins in 2014, followed by a brief stint with the Cincinnati Reds in 2015. Injuries and age began to take their toll, and Gregg's effectiveness waned. He was released by the Reds in May 2015, marking the end of his time in the major leagues.

Throughout his career, Kevin Gregg was known for his durability and ability to adapt to different roles within the bullpen.