Lawton was traded by the Chicago Cubs to the New York Yankees on August 27, 2005. In exchange, the Yankees gave the Cubs pitcher Justin Berg, who was a member of the New York's minor league system since 2003. Yankees manager Joe Torre commented that adding Lawton to the roster gave the team more depth and described him as a "talented player". Lawton got his first hit as a member of the Yankees in his debut with the team on August 27, against the Kansas City Royals. His first Yankees home run came against the Seattle Mariners on August 29. It was noted by MLB.com that Lawton struggled as a member of the Yankees. In 21 games with the Yankees, Lawton batted .125 with six runs scored, six hits, two home runs, and four RBIs. Combined between the Pittsburgh Pirates, the Chicago Cubs, and the Yankees that season, he batted .254 with 67 runs scored, 127 hits, 30 doubles, one triple, 13 home runs, 53 RBIs, and 18 stolen bases 141 games played. At the end of the season, Lawton ranked tenth in the National League in caught stealing (9). Amongst fielders, he was second in fielding percentage (.995) as a right fielder.