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I am trying to translate this sentence, but I can't figure out how to:

The doorkeeper said that even if he were able to enter, he would have found himself facing two other doorkeepers, one stronger than the other.

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3

Your task is tricky.

The doorkeeper said

This part introduces indirect speech, which requires Konjunktiv I in German.

that even if he were able to enter

he would have found himself facing two other doorkeepers,one stronger than the other.

These parts in contrary are counterfactual speech which requires Konjunktiv II in German. Lucky for you, Konjunktiv II beats Konjunktiv I. So the answer is simple:

Der Türsteher hat gesagt, selbst wenn er sich hätte Zugang verschaffen können, hätte er sich zwei anderen Türstehern gegenüber gesehen, einer stärker als der andere.

The phrase sich Zugang verschaffen is more stylish than eintreten. The first hätte leads the row of infinitives, that's a word order exception. The second hätte is in second position, with the previous clause in first position.

And no, no one –really no one– expects C2 speakers to be able to construct such a sentence. This is what you will find in well-written literature.

  • Bemerkung am Rande: Die Situation erinnert stark an Kafkas 'Vor dem Gesetz' (gutenberg.spiegel.de/buch/erzahlungen-i-9763/16) - mal die ersten ca. 10 Zeilen lesen... – Ralf Joerres Mar 16 at 9:49
  • Der Konjunktiv umklammerte Franz. Es wäre ihm möglich gewesen, sich aus dieser unheilvollen Beziehung zu befreien, hätte er die Traumwelten nie betreten, von denen man nachher sagen würde, sie haben ihn den Verstand gekostet. – Janka Mar 16 at 13:22

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