- "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]
Ishmael 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, Gregor 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 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 Gregor that his deal with Kovar betrayed the organization, and the latter takes him in a basement and responded that his decisions are law, then offers him a choice between swearing loyalty to him or die, Oliver refused and before the Pakhan can kill him Talia al Ghul intervened, shooting an arrow into Gregor's hand and saved 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.
After killing the captains that turned against him Gregor fled and told his men to contact the Bratva to recruit new captains loyal to him and to brand Oliver, Anatoly, and Viktor as traitors to the organization. However Oliver and his friends ambushed him in his hiding place killing his men and also Gregor himself before he was killed though he warned Oliver that if he killed him he would only be killing himself. Before his death they tried to question him on what he meant but he told them nothing and he continued to taunt Oliver saying that he is no hero but will ruin everyone that he comes into contact with and dies from his injuries.
Not long after Gregor's death, Anatoly Knyazev succeeded him as the Pakhan of the Solntsevskaya Bratva, but unlike his predecessor; Anatoly is loyal to his fellow Bratva members, as well as the fact that he possessed honor and decency.
Gregor was an opportunist as he saw that his deal with Konstantin Kovar would benefit him and the Bratva even though it went against their ways and it would include the killing of innocent individuals; due to being the leader of the Bratva, he saw that his decisions were the law of the Bratva and he would ruthlessly kill or beat up anyone who stood up to him as he did with Oliver Queen and Anatoly Knyazev.
Gregor was afraid of Kovar as he didn't try to stop his plan for Russia; due to his ruthlessness and also that he himself may be killed, he had no loyalty to anyone but himself as he betrayed many individuals so he could stay alive regardless of the consequences. This included Oliver, Anatoly and the Bratva itself, in the end it was this treachery of his that got him killed.
These negative traits of Gregor's, was what eventually led to his painful yet deserved/justified death at the hands of Oliver Queen.
- High-level intellect/Expert manipulator/Leader: Gregor 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.
- Network: As the former leader of Solntsevskaya Bratva, Gregor has established many connections who provides him aid for various natures.
- "Pakhan" (Russian: Паха́н
[pɐˈxan]) is an informal word for "Father" in 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.
- ‘Arrow’: David Meunier Cast As Ishmael Gregor In Season 5 - Deadline