Complex sentence: Piterman departed in 2007, leaving the club deep in debt after his tenure; after two years of battling against relegation to the third level, Alavés eventually succumbed in 2008--09.
Split into simpler sentences: Piterman departed in 2007, leaving the club deep in debt after his tenure. After two years of battling against relegation to the third level, Alavés eventually succumbed in 2008--09.