|“||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|
Ishmael Gregor was the former Pakhan of the Solntsevskaya Bratva. He was also an ally of Konstantin Kovar. He is the secondary antagonist in the flashback storyline of the fifth season of Arrow.
Ishmael arrived at Cafe Lyublyu after Konstantin Kovar sent his men to shoot up the establishment. Ishmael quickly noticed Oliver Queen, Anatoly Knyazev's "American puppy". Ishmael then noted that he knew who Oliver was and that they only let him in their organization due to special circumstances. When Oliver told Ishmael he earned his place, Ishmael 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 of the casino's profits in exchange for peace between their two criminal organizations. However, Ishmael's deal betrays the Bratva since he gets more of money than the rest of his high ranked associates. Ishmael later arrived at Konstantin Kovar's estate. When he saw Kovar fighting Oliver, he reminded Kovar of their deal. Ishmael then told Kovar that if he killed Oliver, it would come out of his cut.
Outraged, Oliver told Ishmael that his deal with Kovar betrays the Bratva. Ishmael is then prepared to kill Oliver after unsuccessfully trying to get him to reconsider only to be stopped by Talia Al Ghul. Talia shows up stab Ishmael's hand and takes Oliver with her.
After Anatoly questioned Ishmael'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, Ishmael 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 the Arrow, Oliver broke into Kovar's home finding evidence of Ishmael's betrayal, presenting it during the process, the majority of the Bratva captains decide to vote for Anatoly as the new Pakhan; due to this, Ishmael's men decided to mutiny.
After surviving the shootout, Oliver and Anatoly realize that the rest of the Bratva will kill them since Ishmael will make it seem like they're traitors. Anatoly tells Oliver that Ishmael and the rest of Bratva would be meeting at a hockey arena in Moscow. Suiting up as the Arrow, Oliver goes to the hockey arena to kill Ishmael and all of his men with assistance from Anatoly. Oliver stabs Ishmael with an arrow and while fainting, Ishmael tells Oliver that killing him will mean that Oliver has destroyed himself.
Ishmael is taken by the Bratva but eventually dies of blood loss.
- 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 overall leader of Solntsevskaya Bratva, called "Pakhan", he was very much treated with respect.
- Expert Investigator: He took pride in mastering an investigation made towards the "American recruit" to his organization, figuring out who Oliver Queen is, as well as his past deeds and abilities.
- Network: As the leader of Solntsevskaya Bratva, Ishmael has established many connections who provides him aid for various natures. Ishmael had ties with Kovar until he got killed by Oliver.
- Pakhan is what Ishmael was called. Pakhan was like the term used to describe godfather in the Italian mafia.
- In the DC Comics, he was a demonic super villain known as Sabbac. Before that, he was head of the Russian mafia similar to his Arrowverse counterpart.