Reginald Copperbottom with a parachute

He is basically Reginald Copperbottom, but with a parachute.

Appearance
Reginald wears black gloves, black shoes, and two top hats, the upper of which (the darker hat) was from the previous leader. Of the two hats, the bottom one (his original top hat) is a lighter shade of grey. He also has a brown mustache and a golden collar necklace in the shape of a dollar symbol studded with diamonds. He also wears a purple parachute.

Personality
Reginald clearly takes pride in being the leader of the Toppats. In fact, he's clearly not happy when Henry takes over, and he took over the leadership when the previous leader was overthrown. Despite this, he has a sense of honor, asking Henry if he has honor or dignity in the Toppat Civil Warfare ending over his abandonment of Ellie.

Although it first seems hypocritical, Reginald's betrayal of Henry seems justified: He already knew Henry had no problem with betraying someone simply to become more powerful. Although it again can be hypocrisy, seeing as Reginald gave up leadership to save his own skin, he had a choice between allowing the government to cripple the clan, or to give leadership to someone he can take care of later on. It's even shown in the Toppat King ending, where Reginald saves Henry because he has shown himself to be completely loyal to the Toppats.

Reginald is very clearly cowardly and physically weak, as the only times he has any advantage is when Henry is at Reginald's mercy and/or doesn't suspect any kind of attack. If that's not possible, the only thing Reginald can do is run away and tell others to kill Henry.

Overall, Reginald loves to be the leader of the Toppat Clan, but will step down if someone gains his respect by rightfully leading the Toppats.

Henry Stickmin
Henry and Reginald's relationship varies between pathways. Sometimes they like each other, but most of the time, they hate each other.

In his first two games, he didn't particularly like Henry and seemed to have only given him control over the Toppat Clan as a means of self-preservation. This is why he leaps at the chance to kill him in The Betrayed route.

However, in the Toppat 4 Life and Toppat King routes, he sees how much effort Henry is willing to exert for the sake of the Toppat Clan, and so when he finds himself in a similar situation to The Betrayed ending on the latter route, Reginald not only helps Henry up, but gives him control of the Toppat Clan in earnest.

At the beginning of the Toppat Civil Warfare route in Mission, he is utterly appalled at hearing that Henry abandoned Ellie back in the Wall, and leads the remaining Toppats in a mutiny against Henry. Though he isn't above betrayal himself, as demonstrated in The Betrayed, Reginald has a past and potential history of violently dealing with selfish, greedy people above him (notably the previous leader Terrence Suave), so it's possible that watching Henry abandon all sensibility like Terrence did only served to rub salt in the wound. It's also possible that he's simply faking it in order to take the opportunity to retake power in the organization.

In the Revenged route, even when he's faced with the complete and utter destruction of everything he's worked for and is about to die in the oncoming crash landing of his ruined airship, Reginald doesn't waste the chance to get one over on Henry before he dies and shoots his cybernetic spine, making sure to drag his mortal enemy down with him. Although he succeeded in guaranteeing Henry's eventual demise, he dies as well.

Charles Calvin
The two don't interact at all, but they are enemies (since they side with completely opposite factions).

Ellie Rose
While their interactions are very small, it is shown that Reginald is very neutral towards Ellie. Most of Reginald and Ellie's interactions takes place with Henry Stickmin as the main pivot point.

In Toppat Civil Warfare, Reginald uses Ellie's hatred towards Henry's action to get Henry kicked from Toppat Clan so he can take leadership again. This is also shown in PP/TR where Reginald's main determinant on Ellie joining the clan are based on Henry's criminal skills and the fact that he stole the ruby. However despite this, Reginald shows a mass amount of respect for Ellie at the end of Toppat Recruits and Toppat King, where Ellie shows her worth and loyalty to the Toppats.

Right Hand Man
Reg and RHM don’t just seem to be coworkers, but they’re close friends, as the two trust each other. In ItA’s Relentless Bounty Hunter|RBH/RPE path, RHM protects Reginald, he takes on Henry by himself just so Reginald can flee safely.

In the Relentless Bounty Hunter|RBH paths of CtM, he wants to hunt down and capture Henry for getting Reginald arrested. Considering that he wanted revenge, it’s clear that they did care about each other. RHM is also the only person to call Reginald something other than “Chief”, as he calls him Reg, a shortened version of his real name.

Terrence Suave
Although Terrence is out of the picture and likely dead by the time any of the games take place, it's clear that Reginald didn't like Terrence due to his poor leadership and reckless nature, which ended with Terrence being overthrown by Reginald, with Reginald taking Terrence's hat as a trophy.

Trivia

 * Running gag: In every "Rapidly Promoted Executive" path, on the first time Reginald sees Henry in "Completing the Mission", the first word he says when he sees him is "Henry!".
 * In the ending screens for the "Rapidly Promoted Executive", he doesn't look happy with Henry in charge of the Toppat Clan, which leads into Fleeing the Complex's The Betrayed ending.
 * He is one of the only 3 Toppat Clan members to appear in 3 games, along with Wilhelm Krieghaus and Thomas Chestershire.
 * In a Developer Commentary, PuffballsUnited confirmed that he was British (though his accent already makes it partially clear).
 * Compared to the other antagonists, He has the most impact due to appearing more than any other important antagonists, and because he's important in Infiltrating the Airship and Fleeing the Complex, as well as most of the paths in Completing the Mission.
 * Ever since Infiltrating the Airship, Reginald has appeared as a main antagonist in at least one pathway of the games.
 * However, the main antagonist of the series is simply up to debate.
 * Despite his role as the main antagonist being determinant, He is the overall Big Bad of the franchise.
 * He is the only main character that wears gloves.
 * He also appears to be one of the very few characters that have gloves on, the others being Dr. Vinschpinsilstien, Vladimir VonBraun, Grunt, Captain Roland Canterbury and Nacy Popo.
 * He is one of the four characters that wear multiple hats with the others being Sir Wilford IV, Herb Stokes and Peter Maryville.
 * Reginald's age is unknown, but he is heavily implied to be older than Henry because of his long brown mustache and experience leading the clan (most likely around 30-40), and the fact that Henry is 28 during Fleeing the Complex.

Gallery
TBA