Cum meaning 'whenever'
cum + indicative can also mean 'whenever'. For this to be the case, a present main clause takes a perfect in the cum clause; an imperfect main clause takes a pluperfect in the cum clause.
cum multam pecuniam habuit, laetus
est
Whenever he has
much money, he is happy.
cum multam pecuniam
habuerat, laetus erat
Whenever he had
much money, he was happy.
