In his first Major League AB, he hit a home run over the Green Monster in Fenway Park off Terry Adams of the Boston Red Sox.

Also, in 2004, Phillips received the Yankees' Kevin Long "Minor-League Player of the Year" Award in a season where he led all Yankees minor leaguers in batting average (.321) and RBI (101), ranked second in home runs (30), and was voted the Most Valuable Player of the International League All Star Game after hitting a 10th inning walk-off home run.

[1] Phillips's time previous to 2006 at the Major League level had been limited to defensive replacement and late season call-up.

A family emergency (his mother Linda was hurt in a car crash) caused Phillips to miss much of his 2007 spring training with the Yankees.

Due to his inability to make up for lost time and Josh Phelps's (Phillips opponent for a roster spot on the Yankees) outstanding performance (spring training stats include 3 home runs, 14 hits, a .667 slugging percentage, and .389 batting average), Phillips was passed over for a roster spot on the 2007 team.

Throughout the 2007 season, Phillips became an important part of the team as a result of injuries to first baseman Jason Giambi and Doug Mientkiewicz.

On September 2, while batting in the 5th inning against Devil Rays starter Jason Hammel, Phillips was hit on the wrist by a pitch.

On March 28, after hitting .277 in 2008 spring training, he was reassigned to minor-league camp, and he began the season with the Reds' Triple-A affiliate, the Louisville Bats.

He played so well early in spring training that he was considered a lock to make the opening day roster, but a back injury sidelined him for three weeks, and he ended up assigned to Indianapolis instead.

On April 17, 2009, Phillips was traded to the Chicago White Sox in exchange for pitcher Michael Dubee, and assigned to the Charlotte Knights of the International League.