In December 2003, the Milwaukee Brewers acquired Bennett in the Rule 5 draft from Pittsburgh. He made his major league debut on April 6, 2004, against the St. Louis Cardinals at Busch Memorial Stadium and he gave up 2 hits in 1 innings. With the Brewers, Bennett went 1–5 with a 4.79 ERA in 60 appearances. He was well known for keeping the brim of his baseball cap almost completely flat and wearing it so low that the bill was slightly above his eyes. He was granted free agency following the season. Bennett missed the entire 2006 season after undergoing a successful Tommy John surgery.
Atlanta Braves
On September 20, 2007, Bennett made his first career start and his first appearance with the Atlanta Braves. Against the Milwaukee Brewers, Bennett went 5 innings while striking out 8, earning the win. On September 25, Bennett earned a win in relief against the Philadelphia Phillies. He finished the season 2–1 with a 3.46 ERA. In a relief appearance against the Arizona Diamondbacks on May 24, 2008, Bennett recorded his first major league hit in the fifth inning against pitcher Randy Johnson. The Braves suspended Bennett's pay on June 25, 2009, the day after he fractured his hand with an angry punch to a clubhouse wall. Bennett filed a grievance with the Major League Baseball Players Association and continued his rehab assignment at Triple-A Gwinnett. The MLBPA directed the Braves to either repay the suspended funds or grant him free agency. He requested the Braves release him from his contract, and was granted his release on July 30.
Tampa Bay Rays
Bennett signed with the Tampa Bay Rays on August 1, 2009. In eleven games, all relief appearances, Bennett had a 9.95 ERA. He appeared in three games for the Durham Bulls, the Rays' Triple-A affiliate, before being released on May 13, 2010.
Return to the Milwaukee Brewers
On May 25, 2010, Bennett signed a minor league contract with the Milwaukee Brewers, and was assigned to Triple-A Nashville. He came on in relief in twelve games, and was released after the season.
Bennett signed a minor league deal with the Los Angeles Dodgers on May 16, 2014. He made 21 starts for the Triple-A Albuquerque Isotopes, compiling an 8–6 record with a 3.82 ERA. He made one start in winter ball after the season, managing only one out. After the out, he lost feeling in his pitching hand and took himself out of the game. He decided to retire from baseball the following March.
Personal life
In early 2015, Bennett began giving baseball lessons to local youth athletes in Middle Tennessee near his home in Mt. Juliet. Initially borrowing places to train, his business soon grew large enough to necessitate owning his own facility: Jeff Bennett's Baseball Academy, near Lebanon, Tennessee. He and his wife have four children.
