 In 2000, Benjamin signed a contract with the World Wrestling Federation (WWF) and was placed in its developmental territory Ohio Valley Wrestling (OVW). There, he formed a tag team with Brock Lesnar, where he was wrestling Brock's wrestling coach at the University of Minnesota. Together, they were known as the "Minnesota Stretching Crew," and they held the OVW Southern Tag Team Championship on three occasions. The first two reigns occurred during February and July 2001. They won the title for a third time from Rico Constantino and The Prototype on October 29, 2001. After Lesnar was called up to the main roster in November 2001, Benjamin formed a tag team with Redd Dogg Begnaud called "The Dogg Pound" and once again won the OVW Southern Tag Team Title on July 17, 2002. Benjamin then wrestled at several house shows for the main WWE roster and eventually made his WWE television debut on Sunday Night Heat as a face character.
