Skipper was born in Arvada, Colorado, a suburb of Denver. He played football at Ralston Valley High School, where he earned 5A all-state recognition as a senior. During his senior season, he helped get Ralston Valley to the state semifinals. Skipper received numerous scholarship offers, ultimately choosing the University of Arkansas.
College career
As a freshman, Skipper played in all twelve of the Razorbacks' games, starting eight. He blocked three field goal attempts, a school single-season record. He was named a Consensus All-American. As a sophomore, Skipper started all 13 games of the season and earned an Associated Press All-SEC honorable mention. As a junior, he started all 13 games and was named to ESPN's All-SEC team. As a senior, he made the All-SEC team of ESPN, Phil Steele, Athlon Sports, Lindy's Sports, Sporting News, and the Coaches Poll.
Professional career
Skipper went undrafted during the 2017 NFL Draft. It was speculated that he went undrafted due to a chronic blood condition that was discovered during prospect evaluations. After not receiving a contract as an undrafted free agent, Skipper received an invitation to attend the Dallas Cowboys' rookie mini camp as a tryout candidate.
On September 25, 2017, Skipper was signed to the Detroit Lions' practice squad. He was promoted to the active roster on October 26, 2017. On October 31, 2017, he was waived in order for the Lions to sign Don Barclay and was re-signed to the practice squad. He signed a reserve/future contract with the Lions on January 1, 2018. On September 1, 2018, Skipper was waived by the Lions and was signed to the practice squad the next day. He was released on September 5, 2018.
On January 8, 2019, Skipper was signed to the New England Patriots practice squad. Skipper was a part of the Patriots Super Bowl LIII championship team when they defeated the Los Angeles Rams 13-3. He signed a reserve/future contract with the Patriots on February 5, 2019. He was released during final roster cuts on August 31, 2019. He was signed to the practice squad the next day.
On October 16, 2019, Skipper was signed by the Houston Texans off the Patriots practice squad. He was waived on November 11, 2019.
Detroit Lions (second stint)
On November 12, 2019, Skipper was claimed off waivers by the Detroit Lions. He was waived on November 22 and re-signed to the practice squad. He was promoted to the active roster on December 14, 2019.
