In the summer of 2008, then Liverpool manager Rafa Benitez was looking to bring in a new right-back, following the exit of the brilliantly consistent Steve Finnan. Degen was a player the Spaniard seemed particularly keen on, believing the Swiss defender would be the perfect replacement for the former Republic of Ireland international. Benitez got his man, and upon his arrival from Dortmund proclaimed: "Degen is an offensive player with great energy and a winning mentality. His strength is going forward and I am confident he will be prove to be a quality addition to our squad." As it turned out, he played so little that we barely got the opportunity to see if Benitez's assessment was correct or not. Degen had a disastrous start to his Reds career, breaking two ribs and puncturing his lung in a collision with teammate Sami Hyypia, ruling him out for two months in the process. On his comeback game in November 2008, he broke his metatarsal after a challenge on him by Gareth Bale, and he couldn't hide his emotions after the game: "It is the saddest event of my life I keep asking myself if I did something wrong in a past life." He didn't make one league appearance in his first season at Anfield, and although in his second year he enjoyed a brief run in the team, often as a right winger, he racked up just 12 appearances for Liverpool in two years. He was loaned out to Stuttgart at the end of the 2009/10 campaign, and joined on a permanent deal a year later.
