Upon graduation, Kendrick turned down a scholarship to play college football, instead signing a contract to begin his pro baseball career with the Phillies.

After a slow ascent through Minor League Baseball (MiLB), he made his MLB debut in 2007, and was a member of the starting rotation of the 2008 World Series Championship team.

Kendrick began his career in the lower levels of the minor league system, and struggled mightily.

[6][2] A feature article in Phillies magazine noted, His first three seasons, in the Gulf Coast League, and various Class A stops, weren't encouraging.

However, according to Steve Noworyta, Phillies assistant director of player development, Kendrick's "mound presence and his maturity", as well as the fact that "nothing really seemed to bother him" contributed to his promotion.

[1] He came in fifth place, ultimately losing to Ryan Braun, in 2007 National League Rookie of the Year Award voting.

As such, he spent the majority of the 2009 season in the minor leagues, working on developing his change up, which proved to be an arduous process.

Ultimately, after learning a new grip from Justin Lehr, he had a eureka moment during a bullpen session in 2009; he developed the pitch, and made it back to the major leagues "for good" near the conclusion of the season.

[2] Despite initially losing a competition for the fifth spot in the Phillies starting rotation during spring training to Jamie Moyer, an injury to Joe Blanton thrust Kendrick into the fifth spot in the Phillies rotation, the fourth consecutive year during which he had held that role for at least a short time.

[14] Kendrick's inconsistency continued in 2011, when he "flip-flopped between the rotation and the bullpen all season", performing as a spot starter and long reliever.

[18] During the season, he improved against left-handed hitters, performed strongly against divisional opponents, and posted a career-best 3.22 ERA.

Once again, Kendrick was not a member of the opening day starting rotation, as Blanton and Vance Worley rounded out the final two spots after Hamels, Halladay, and Lee.

[24] On September 18, he was scratched from his scheduled start due to right rotator cuff tendinitis, which may have contributed to his poor pitching down the stretch.

He had initially planned on making his next start, but the Phillies announced on September 20 that Kendrick had been shut down for the remainder of the season after receiving a second opinion on the injury.

[27] Contradictorily, one scout suggested that because he throws strikes with great frequency and has a propensity to induce groundballs, he would be a strong value option for the Phillies.

[28] Ultimately, the Phillies agreed with the latter, and signed him to a one-year, US$7,675,000 contract in the final year before he is eligible to be a free agent.

[1][42] Kendrick elected retirement but after sitting out the 2018 season, he became a guest instructor at Phillies’ 2019 Spring Training.

[43] When Kendrick was first promoted to the major leagues, he relied almost exclusively on a sinker, but as he became more predictable, he had to adjust by adding pitches, including the changeup, cutter, and curveball that now comprise his repertoire.

He lacks requisite confidence in his secondary pitches, however, which contributes to batters being able to consistently make solid contact against him.

[18][24][47][48] When pitching, he maintains constant equanimity and seeks to avoid showing emotion, a trait he learned from his father and has embodied since playing Little League Baseball.

[51] Subsequently, the ring was found in a swampy area of Bothell, Washington, by Snohomish County Sheriff's deputies.