O'Shaughnessy was selected by the Kansas City Chiefs in the fifth round, 173rd overall, in the 2015 NFL draft.[6] During O'Shaughnessy's two years in Kansas City, he recorded eight receptions for 86 yards.[7][8]
New England Patriots
On April 29, 2017, the Chiefs traded O'Shaughnessy and a sixth-round selection in the 2017 NFL draft to the New England Patriots for a fifth-round selection.[9] He was released by the Patriots on September 2, 2017.[10]
On September 10, 2017, in his Jaguars debut, O'Shaughnessy had one reception for 18 yards in a 29–7 victory over the Houston Texans.[12] In Week 16 against the San Francisco 49ers, he had five receptions for 39 receiving yards and a receiving touchdown.[13] He finished with 14 receptions for 149 receiving yards and one receiving touchdown.[14]
In the 2018 season, O'Shaughnessy finished with 24 receptions for 214 receiving yards.[15]
On March 21, 2019, O'Shaughnessy re-signed with the Jaguars.[16] In Week 5, against the Carolina Panthers, O’Shaughnessy suffered a torn ACL and was ruled out for the rest of the season.[17][18] He finished with 14 receptions for 153 receiving yards and two receiving touchdowns.[19] He was placed on the active/physically unable to perform list by the Jaguars at the start of training camp on August 1, 2020.[20] He was moved back to the active roster on August 12.[21]
O'Shaughnessy re-signed with the Jaguars on March 17, 2021.[22] He was placed on injured reserve on September 22, 2021, after suffering an ankle injury in Week 2.[23] He was activated on November 27.[24]
Chicago Bears
On April 18, 2022, O'Shaughnessy signed with the Chicago Bears.[25] He was released on August 30, 2022.[26]