Skipper was signed by the Pittsburgh Steelers as an undrafted free agent in 2019. After making the Steelers initial 53-man roster, Skipper was waived prior to Week 1 on September 7, 2019.[9]
On September 9, 2019, Skipper was claimed off waivers by the New York Giants.[10] He was waived on October 22, 2019, and re-signed to the practice squad.[11]
On November 19, 2019, Skipper was re-signed by the Steelers off the Giants practice squad.[12] On December 30, Skipper was re-signed by the Steelers to a two-year contract.[13] He was waived on September 5, 2020.[14]
Skipper was signed to the Tennessee Titans' practice squad on September 15, 2020.[15] He was elevated to the active roster on November 21, November 28, December 5, and December 12 for the team's weeks 11, 12, 13, and 14 games against the Baltimore Ravens, Indianapolis Colts, Cleveland Browns, and Jacksonville Jaguars, and reverted to the practice squad after each game.[16][17][18][19] He was placed on the practice squad/injured list on December 15, 2020,[20] and restored to the practice squad on January 6, 2021.[21]
He was signed to a futures contract by the Titans on January 11, 2021.[22] Skipper was waived by Tennessee on July 25, 2021.[23]
On July 31, 2021, Skipper signed with the Atlanta Falcons.[24] He was waived on August 31, 2021.[25]
On December 6, 2021, Skipper was signed to the Tennessee Titans practice squad.[26] After the Titans were eliminated in the Divisional Round of the 2021 playoffs, he signed a reserve/future contract on January 24, 2022.[27] He was waived on May 2, 2022.[28]
On June 1, 2022, Skipper signed with the Pittsburgh Steelers.[29] He was waived/injured on August 15, 2022.[30] He reverted to injured reserve the following day. He was released on August 24, 2022.
On November 17, 2022, Skipper was drafted by the Seattle Sea Dragons of the XFL.[31]
On June 16, 2023, Skipper was traded, along with the 40th pick in the XFL Rookie Draft, to the Arlington Renegades in exchange for George Moore and the 46th pick.[32] Skipper re-signed with the Renegades on February 2, 2024.[33] He was placed on injured reserve on April 10, 2024.[34] He re-signed with the team again on September 30, 2024.[35] He was released on April 16, 2025.
