Complex sentence: Despite being skimmed by them several times, the gang often pay Eddie their debts (often before heading on vacation at the end of a season) and provide financial assistance if need be.
Split into simpler sentences: Despite being skimmed by them several times, a certain financial trust exists between Eddie and the group. For instance, the gang often pay Eddie their debts (often before heading on vacation at the end of a season) and provide monetary assistance if need be.