Dukov

Dukov is a drunken, womanizing Russian and is one of the three surviving mercenaries hired by Allistair Tenpenny for an expedition into Fort Constantine. He is now retired to his estate (Dukov's Place) along the east bank of the Potomac in the D.C ruins. He spends his time drinking lots of alcohol and taking Jet with Cherry and Fantasia.

You Gotta Shoot 'Em in the Head
During the You Gotta Shoot 'Em in the Head quest in a dialogue with the Lone Wanderer, Dukov states he is no bigot as Mister Crowley claims and even had a Ghoul party girl once. To complete the quest you must obtain Dukov's Special Key from him. There are a variety of ways to do this.

Killing Dukov
If you inform him that you are "going to put a bullet in his head" he will rise to the challenge - the only difference is that you have VATS. Splatter his head at point blank and his party girls will not flee.

You can execute him outright, without provoking him, but his party girls will flee and not talk to you. Followers have a high risk of killing the innocent party girls and will result in a loss of karma.

Non-violent solution
Talk with Cherry, she will pickpocket the key if you pass a speech check. In return she wants you to escort her to Rivet City for a karma bonus.

Alternatively, if you have the Black Widow perk, you can convince him to just give you the key.

Appearances
Dukov appears only in Fallout 3.

Glitch
There is a bug where a mirelurk will come through the front door and kill Dukov. Note: (Player-observed, X360 and PS3 Versions) After escaping from Enclave forces in the Jefferson Memorial, I encountered a mind-controlled Deathclaw and an Enclave Officer. I retreated into Dukov's place, and the Deathclaw also came inside. Glitch, maybe?

There is a glitch that occurs after you kill Dukov. If you wait two weeks and return to loot his house, a Deathclaw will enter the room after you have stolen a few items. This only occurs once. If you die, it will not occur again.

Even though Dukov always talks about drinks - and that you should serve yourself - if you steal more than two bottles he will become hostile and attack you. The girls will be marked hostile as well. However, this can be avoided if you take drinks from the cabinet in the bedroom upstairs.

There is a glitch where dukov's special key cannot be used with Fort Constantine.

There is also a glitch where the Black Widow perk will not affect Dukov.

Related quests

 * You Gotta Shoot 'Em in the Head