...does anyone know the context behind this? Assuming there is one

Looking through the artist's history on Pixiv, it seems he just simply likes drawing anything associated with the Soviet Union.

It is time for the ultimate camping trip! The concentration camp!

Tapper said:

Looking through the artist's history on Pixiv, it seems he just simply likes drawing anything associated with the Soviet Union.

Huh, fair enough I guess

It's Soviet Army's captain and sergeant

Is that the man, the legend, the first President of the Chechen Republic of Ichkeria, Dzhokhar Dudayev?

SCPKing1835 said:

Is that the man, the legend, the first President of the Chechen Republic of Ichkeria, Dzhokhar Dudayev?

I don't think so, unfortunately. He served in the Soviet Air Force, not in the Army (as we have two Army officers in the picture). Missed opportunity imo.

SCPKing1835 said:

Is that the man, the legend, the first President of the Chechen Republic of Ichkeria, Dzhokhar Dudayev?

Now you mentioned it. I think no one had tried asking the artist if the soldiers look similar to RL individuals.

T34-38 said:

Now you mentioned it. I think no one had tried asking the artist if the soldiers look similar to RL individuals.

He's definetly based off Dudayev. But yeah it's a shame that he isn't wearing an Air Force general uniform like bagd mentioned.

Edit: Oh and I found this randomly on Google when I looked up "Dzhokhar Dudayev".