In seasons 1-3, both 21 and 24 were known as the Monarch's best men, much to his displeasure. After 24's death, for most of season 4, 21 served as the Monarch's right hand man, until he quits in Operation P.R.O.M. Despite 21 saying he quits, the Monarch still thinks 21 is loyal to him and believes 21 is on some kind of undercover mission in the Venture compound. 21 later returns to work for the Monarch and becomes their sole henchman after the Cocoon along with a majority of the henchman are destroyed. It is also shown despite Gary closely working with The Monarch the latter never knew his first name asking who "Gary" was after the Cocoon's destruction. In season 6 after the destruction of the Cocoon and their moving into the Monarch's family mansion the Monarch and 21 are shown to have become closer, this is shown by them playing games together such as 20 questions and uno. It also seems that the Monarch has come to view 21 more as an equal rather than a subordinate, even apologizing to him after an angry outburst in Faking Miracles a courtesy which in the past he has claimed that a villain should never give their henchmen.