#5 ALAN SHEARER
Former Newcastle United striker Alan Shearer had it all figured out when it came to planning his coaching career upon retiring in 2006. A couple of years of rest and TV punditry followed by a UEFA license, a small assignment with less pressure to start off with was his mantra. Alas, circumstances do not care even for the best of plans. Unlike the other one-club managers Shearer had the most difficult of starts to his coaching career, a baptism of fire indeed.
Despite being passionate for Newcastle he had refused to begin there multiple times, but he had to change his mind when the club was in dire straits. In April 2009, after his predecessor took ill, Shearer was appointed the coach for remaining eight games of the season, with relegation looming.
Unfortunately, Shearer's efforts weren't enough to turn the tide and Newcastle could only secure five points from a possible 24, including a solitary win against Middlesbrough to go down after 16 years in the top flight. He quit just after the season and retreated to punditry which he's still doing till date. Perhaps having to witness a beloved club reach such lows under his watch was a big enough bummer to not pursue coaching altogether.