After an initial period in charge where everything went right, the wheels started to come off in the Euro 2000 campaign. England beat rivals Germany 1-0 but were beaten by both Romania and Portugal and failed to qualify for the knockout stages.
The English media, as famously harsh as they are fickle, turned on Keegan for England's poor displays.
The final straw for Keegan occured at the final match at the old Wembley, as Germany won 1-0. With the media calling for his head and Keegan under severe pressure, he resigned.
Keegan again said he was walking away from the game and needed time to re-charge after his England ordeal. But the rest period only lasted seven months, with Keegan once again surprising everyone by taking over at Manchester City.
The four years in charge of Man City were largely fruitless, but Keegan showed he could be a shrewed manager guiding City to mid table safety on a shoe string budget.
In 2005 Kevin Keegan retired from football completely.
He was burnt out, and the game had changed massively from his time as a player. Keegan didn't like the direction football seemed to be taking, and stepped away from the competitive game. He set up the Soccer Circus roadshow in the hope of training young players and passing on some of his vast knowledge.
Then, on the 16th of January 2008, after three years away from the game, Keegan returned to the his spiritual home as manager of Newcastle.
Yet after just one month in charge Keegan had to be talked out of resigning by owner Mike Ashley. Keegan felt undermined after Ashley had appointed Dennis Wise as Director of Football.
Wise would take charge of the transfer dealings both in and out of the club, and Keegan wasn't happy with this. Ashley eventually talked Keegan around, suggesting that it would give Keegan more time on the pitch and that it was the best way forward.
Keegan chose to stay, perhaps because the size of the challenge ahead of him enthralled him. And after an initially poor start, losing his first eight games in charge, Keegan guided Newcastle to safety.
Strangely for the ever optimistic Keegan, after a defeat to Chelsea he told a press conference that Newcastle would never challenge for major honours again. Ashley was furious, but Keegan had drawn attention to the lack of ambition at the club.
Throughout the summer rumours of Keegan's unhappiness under the Ashley regime persisted. Ashley made little or no money available, and players were offered around the Premiership.
James Milner was sold without Keegan's knowledge, and rumour has it that Michael Owen being offered around was the straw that broke the camel's back.
If you've lasted this long and read this much I hope I've shown that as a player Keegan never gave up. If he wanted to achieve something it was up to himself and he worked hard to attain it.
His career as a player is spectacular, but it was all down to him. He shaped his own destiny.
This is perhaps Keegan's downfall as a manager, because no matter how hard you try. and no matter how well you organise, you cannot foresee every outcome.
During his first term as Newcastle manager, Keegan signed who he wanted and played the way he wanted—but he just couldn't win the title no matter how hard he tried.
Something always conspired against him. It was this that eventually led him to walk away the first time.
At England, blind optimism carried him on. He really believed his approach could carry England forward, and when it couldn't again he resigned.
During his charge at City, Keegan actually seemed at peace with himself. But during this period they never challenged and this going with the flow was never going to be good enough for Keegan.
And now, back in charge of Newcastle, Keegan finds his authority eroded, his responsibility diminished, and once again he sees all the outside influences he can't control sniping at his heels, driving him mad.
As I write this, depending on which media source you listen to, Keegan is either still in charge or has resigned. Personally, I hope he resigns. Mike Ashley doesn't know what he's doing and Keegan is too good for him.
But if Keegan does go, a little bit of every supporter goes with him.
We'll all miss his optimism.
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