He previously played for the Pittsburgh Steelers, Oakland Raiders, New York Giants, Tennessee Titans, Arizona Cardinals, and Minnesota Vikings.

[2][3] Throughout training camp, Riley competed for a roster spot as a backup cornerback and special teams player against Khalid Wooten, Marqueston Huff, Cody Riggs, Jemea Thomas, and Ri'Shard Anderson.

[6] Riley entered training camp as a backup cornerback and competed for a roster spot against B. W. Webb, Valentino Blake, Kalan Reed, Bennett Okotcha, Cody Riggs, and Josh Aubrey.

[7] On September 2, 2016, the Titans officially waived Riley as part of their final roster cuts, but signed him to their practice squad the following day.

[11] Riley competed for a roster spot as a backup safety against Brynden Trawick, Da'Norris Searcy, and Denzel Johnson.

[12] Head coach Mike Mularkey named Riley the backup free safety to start the season, behind Kevin Byard.

[17] Riley was reunited with Giants assistant defensive backs coach Deshea Townsend, who had previously held the same position with the Titans.

Riley started training camp as a cornerback and competed against Donte Deayon for a roster spot as the first-team nickelback, but was moved to safety after Darian Thompson suffered a hamstring injury.