Over the following months, the Pretty Boy Killers faced teams including the Washington Bullets, the Alpha Class, the Get Along Gang, the All Night Express, and War Machine.

[8][9] In August 2016 at Field of Honor, the Pretty Boy Killers took part in a gauntlet match to determine the number one contenders to the ROH World Tag Team Championship that was won by The Addiction.

[10] The following month at All Star Extravaganza VIII, they took part in a four way match to determine the number one contenders that was won by Colt Cabana and Dalton Castle.

In spring 2017, Taylor joined the stable The Rebellion, which also included Rhett Titus, Kenny King, and Caprice Coleman.

In December 2017 at Final Battle, Taylor competed in a four-way match for Kenny King's ROH World Television Championship that was won by Silas Young.

The following month at Masters of the Craft, Taylor teamed with SoCal Uncensored in another loss to Bullet Club.

At the ROH and New Japan Pro-Wrestling G1 Supercard pay-per-view in April 2019, Taylor, Bully Ray, and Silas Young lost to Flip Gordon, Juice Robinson, and Mark Haskins in a "New York City street fight".

[20] Taylor successfully defended his title against Bandido at Best in the World in June 2019 and against Tracy Williams at Summer Supercard in August 2019.

[20] In September 2019, a storyline aired in which ROH ended Taylor's contract due to him criticizing the promotion's lack of interest in his booking.

[21] At Death Before Dishonor XVII later that month, Taylor retained his title by beating Dragon Lee, Flip Gordon, and Tracy Williams in a four way match.

At the same event, Kaun, Moses, and O'Shay Edwards (substituting for Taylor) lost the ROH World Six-Man Tag Team Championship to The Righteous (Bateman, Dutch, and Vincent).

[25] In August 2023, Taylor won an eliminator tournament to receive a shot at the ROH World Television Championship.