#2 Kenny Dalglish
For a while in the 1990s, it seemed like 'King Kenny' would continue his amazing playing career into management for a long time. After taking over as player-manager in 1975, Dalglish won Liverpool three league titles in four years, adding two FA Cups in 1986 and 1989 for good measure.
It's a sad fact that English teams were banned from European competition during this period, for that Liverpool side, with John Barnes and Peter Beardsley, could have seriously challenged under Dalglish's tutelage.
Astoundingly, at the time of his resignation in 1991, Liverpool were three points ahead in the league and there's every reason to expect that they would have emerged still on top.
In October of that year, he sought a new challenge with Blackburn Rovers in the Second Division; within four years, Dalglish took them to an incredible EPL title in 1994/1995, only topped by Leicester in terms of shock value.
Again, he quit while he was ahead, and he would go on to win only a Scottish League Cup with Celtic in 2000 and a Football League Cup back with Liverpool in 2012.
His trophies in coaching would make most people proud but it says so much about Dalglish's standing in football that he's mostly remembered for his playing career. Perhaps Scotland's greatest ever player, perhaps Liverpool's greatest ever player too, Dalglish was a world-class talent: he didn't score the most goals but he influenced play immeasurably and transformed teams when he played for them.
He succeeded the famous Lisbon Lion generation and fired Celtic to four league titles and four Scottish Cups in 5 years from 1972 to 1977; after his move to England, Dalglish led the team from the front as Liverpool dominated the European Cup, winning in 1978, 1981, and 1984.