2008–2009
On September 12, 2008, West signed a three-year $12.7 million contract with the Cavaliers. He was moved to the starting shooting guard position at the beginning of the season, due to the acquisition of Mo Williams.
He became a starter for the Cavaliers, who won a league-best and franchise-record 66 games during the regular season and went 39-2 at home. In addition to his role as the starting shooting guard, he also served as the backup point guard, manning the position when Mo Williams was not in the game. He emerged as a talented backcourt defensive player, guarding a variety of players ranging from the 6'3" Ben Gordon to the 6'10" Hedo Turkoglu. Offensively, he proved to be a capable outside shooter, with a field-goal percentage of 46% (and 40% on three-pointers), and maintained his reputation as an athletic and hard-nosed driver with the ball. West, Williams, Zydrunas Ilgauskas, and Anderson Varejão came together to form a supporting cast for franchise player LeBron James.
On March 2, 2009, against the Miami Heat, West set a career high with 8 steals.
In the playoffs, West's averages shot up to nearly 14 points per game, despite struggling with his 3-point shot much like his backcourt-mate Williams, whose shooting struggles in the playoffs were well documented. Further, the Cavs' lack of scoring punch on the bench forced West to take on extremely high minute loads. He averaged 42 minutes per game throughout the postseason, and in the Eastern Conference Finals against the Orlando Magic (which the Cavs lost in 6 games due in part to, again, outside shooting struggles from Williams and West) he played over 45 minutes per game, more than any other player in the series. In addition to this, he drew the defensive assignment of Hedo Turkoglu, who had a 7-inch height advantage, to allow James to play the "rover". West was able to stop Turkoglu's facilitation of the Magic offense in spurts, but the height advantage was too much, as Turkoglu helped to dominate the Cavalier defense throughout the series. West set a new career playoff high in points, with 22 in a losing effort in Game 6 against the Magic when the Cavs were eliminated.
But he did go home and bang Lebron's Mama to Lionel richies "All Night Long".. ALLL NIIIGHT!!