to have taken
Nunca debí haber tomado dinero prestado de él.
I should never have borrowed money from him.
Por supuesto que podría haber tomado su auto.
Of course I could have taken his car.
No debiste haber tomado prestado el auto de Tom.
You shouldn't have borrowed Tom's car.
Tom ya debería haber tomado una decisión.
Tom should have made a decision by now.
Debería haber tomado la pastilla azul.
I should have taken the blue pill.
El hombre negó haber tomado el dinero.
The man denied taking the money.
Debió haber tomado el colectivo equivocado.
He must have taken the wrong bus.