- "Of course you don't because you don't understand that circumstances are what makes a thing poison or nectar. You believe your fool's errand to kill Kovar because you think that you are responsible for this darkness that's inside you. Like baby blaming himself for being left out in the cold by his mother. If it weren't for that island... You would be that harmless American douchebag that you pretended to be in Kovar's casino."
- —Ishmael Gregor to Oliver Queen[src]
Pakhan Gregor arrived at Cafe Lyublyu after Konstantin Kovar sent his men to shoot the establishment. Gregor quickly noticed Oliver Queen, Anatoly Knyazev's "American puppy". Gregor then noted that he knew who Oliver was and that they only let him in their organization due to special circumstances. When Oliver told Gregor he earned his place, Gregor praised Oliver's eagerness. Kovar then told Oliver of Kovar's plan on expansion with a casino. He then sent Oliver to play as a rich American playboy once more to infiltrate Kovar's casino and blow it up.
Behind the scenes, Ishmael and Kovar agreed to a deal, in which the Bratva would get a cut out of the casino's profits in exchange for stopping the turf war. Gregor later arrived at Konstantin Kovar's estate. When he saw Kovar fighting Oliver, he reminded Kovar of their deal. Gregor then told Kovar that if he killed Oliver, it would come out of his cut.
Outraged, Oliver told Pakhan Gregor that his deal with Kovar betrayed the organization, the latter takes him in a basement and respond that his decisions are law, then offers him a choice between swearing loyalty to him or die, Oliver refused and prior that Pakhan can kill him Talia al Ghul intervened stabbing Gregor's hand and saving Oliver's life.
After Anatoly questioned Gregor's deal with Kovar, the former was beaten badly so he and Oliver began a plot to kill the Pakhan. However, before they could decide their moves, Gregor and his men attacked them in the hospital where Anatoly had recovered. As they were about to be killed, Anatoly invoked the "spros dopros", a Bratva trial in which the Pakhan is asked to answer for his deeds. As Oliver broke into Kovar's home finding evidence of Gregor's corruption, presenting it during the process, the majority of the Bratva captains decide to vote for Anatoly as the new Pakhan; due to this, Gregor's men decided to mutiny.
- Keen intellect/Manipulation/Expert leader: Ishmael was a crafty mafia boss and had great insight into people's character, recognizing Oliver Queen's fighting nature, as well as his "douche playboy" past, and using it to his own ends. As the former leader of Solntsevskaya Bratva, called "Pakhan" (equivalent of a Mafia "godfather"). He was so important and respected in the criminal organization that he made Anatoly Knyazev, his supposed friend and one of the sub-bosses, to worry about showing proper respect to him.
- Expert investigator: Ishmael prided himself on conducting a masterful investigation of a new "American recruit" into his organization, figuring out Oliver Queen's identity, as well as his past deeds and talents.
- Network: As the former leader of Solntsevskaya Bratva, Ishmael has established many connections who provides him aid for various natures.
- "Pakhan" (Russian: Паха́н
[pɐˈxan]) is an informal word for "Father", usually used to describe gang leaders in Russian Mafia, such as the Solntsevskaya Bratva organization.
Behind the scenes
- In the DC comics, Ishmael Gregor was also a Russian crime boss, eventually taking on the mantle of a demonic supervillain Sabbac.