Martin Allen's career as a manager has been littered with success and failure.
While at his first club, Barnet, he took the side to the top of the league within the first year, after bringing together a squad on nothing more than a shoestring budget.
However, Allen's ambition got the better of him. While Barnet lay in a promising position in the Conference, he left for Second Division Brentford.
Now Allen's success at Barnet may well have warranted the move to the football league club, but many Barnet fans would agree the club would surely have completed promotion in the 2003-2004 season had Allen stayed until the end.
Barnet crashed out to Shrewsbury Town in the playoffs that season, as Allen saved the Bees from relegation in the last remaining months of the season.
He did not stop there however. In his next two seasons, Allen turned the relegation candidates into promotion contenders with successive playoff finishes.
Although he was denied by first Sheffield Wednesday and then Swansea City, he had clearly taken Brentford on as a team. A success that climaxed with him knocking Sunderland out of the FA Cup in the fourth round.
Allen's ambition swelled further, and targeted extra funds to finalize that crucial promotion push.
However, his ambition could not be matched by the clubs board, and he tendered his resignation at the end of the 2005-2006 season.
Allen then found a club, whose financial ambition could match his own on the pitch, Pete Winkleman's Milton Keynes Dons.
He reached the playoffs for the third time in his managerial career, but was yet again denied at the semi-final stage after loosing to Shrewsbury Town.
Leicester City soon came calling for the impressive Allen, who despite his inability to produce instant promotion, could guarantee stability to any club.
However, Allen came across trigger-happy Milan Mandaric and started a nightmare at the Walkers Stadium, which lasted just four games.
Arguments over potential transfers involving Jimmy Floyd Hasselbaink and Derek Riordan fueled speculation that Allen was set to leave the Championship Club.
After taking a year out of the game Allen joined League One Cheltenham Town, but unlike at previous clubs he has not been able to turn the clubs fortunes around.
Cheltenham struggled last season, and staved off relegation on the final day of the season.
Allen has not had much luck stemming the flow this season. The club lie twelve points from safety, routed to the bottom of League One.
As if Cheltenham's plight could not get worse, the club have entered huge financial difficulties, and look set to enter administration anytime soon.
The problem is if the club does not concede the inevitable and enter administration before March 10, the standard 10 point deduction that would normally be enforced this season would be in place for next season. This would leave the club with a huge uphill struggle and on the brink of successive relegation.
Now the club have insisted that administration would be the final straw and a point that they do not want to get, without admitting that it is a distinct possibility.
To add to the situation, Allen was told that to cut costs players are free to leave the club.
Lloyd Owusu has already gone to Brighton with a host of players expected to leave before the end of the week.
It is important that the clubs biggest asset, Allen, does not follow suit.
His departure after what is sure to be certain relegation this season would be dreadful for the club, and administration would make their start in league two execrable.
Would the former Barnet manager cling on to Cheltenham and help them challenge in League Two?
Or would the ambition that has followed the eccentric manager continue as he looks to further his football league career?
Allen has not hesitated from leaving clubs whatever extreme the club was in. He would not defer from moving on from Cheltenham.
Allen's up and down career has taken him all around the football pyramid. But would this impending relegation be too much of a step down for 'Mad Dog'?