After seeing his tenures at Newcastle United and Blackburn Rovers curtailed soon after the ownership of their respective clubs changed hands, now he has been forced to look on as a potential takeover of his new employers has been claimed before he has even got his feet under the desk.
Of course, it may not be the desk he would most like to be placing his family pictures and executive toys upon. As he has claimed before, though admittedly perhaps taken a little out of context, the former Bolton boss believes he would acquit himself at the Bernabeu or San Siro every bit as well as he expects to at Upton Park.
Nevertheless, he has taken a job at a club in a division it doesn't want to be in, with several players who don't want to be there, preparing to move to a stadium to which many fans don't want to go.
Wednesday was bookended by confirmation that he was the new manager of West Ham United in the morning and being questioned about reports that Tony Fernandes was lodging a bid to buy the club in the evening.
Fernandes, the Malaysian owner of Formula One constructor Team Lotus, has previously shown an interest in buying the club which he claims to support.
After recently being quoted as expressing his relief that he did not end up getting involved following the Hammers' relegation from the Premier League, yesterday he said on Twitter: "For all you West Ham fans an offer has gone to the present owners of West Ham. Let's see if they accept."
Clearly, a 105-character tweet is hardly the most official channel by which to announce intention of purchasing any business, and it has left Allardyce "bemused" and current club owners - Davids Gold and Sullivan - into making seperate statements at odds with each other.
"The whole thing is nonsense," said Sullivan. "I can assure Sam he has an unbreakable two-year contract and he is the perfect man for the job.
"I can only think the motivation for this "takeover" bid is PR. If there's a Roman Abramovich or Sheik Mansour Mark II out there, then fine. But when someone offers to buy your club for buttons and does it via Twitter it is most unhelpful at a time when we are trying to rebuild West Ham."
Gold, however, took a slightly different view: "We are interested in finances coming into the club," he said, possibly while standing in front of his helicopter even if there were no cameras around to film him doing so for once. "I would be happy to sit down with Tony with a view to him joining the board and bringing in desperately needed finances."
These conflicting statements - an aggressive rebuke from Sullivan, a cautiously welcoming hand extended by Gold - are typical of the way in which the pair operated as they oversaw the Hammers' shambolic campaign last season which ended in relegation.
The only other time Allardyce has worked under an ownership of as unpredictable as this was when Mike Ashley took over at Newcastle. He lasted less than a year on Tyneside before the fans turned on him and Ashley leapt upon the opportunity to make his mark at his newly acquired club and got rid.
Neither of the next two managers at St James' Park - Kevin 'Geordie Messiah' Keegan and Joe 'F*@$!' Kinnear - enjoyed a win percentage as high, but his time in the North East remains the one real blot on Allardyce's copybook.
Already there are plenty of Hammers fans who have voiced their displeasure at the appointment, falling over themselves to complain that the team will not play 'the West Ham way'. All supporters want their team to play attractive football, but when a major rebuilding job is on the cards following relegation and an expected player exodus then you have to forgo the tiki-taka in favour of a more industrial approach. Besides, the last person to try and play football at Upton Park was Gianfranco Zola, and he almost got the club relegated a year before Avram Grant finished the job off so emphatically. Surely any type of game plan from Allardyce is better than none at all, which is what Grant seemed to offer.
Many will point to his trademark long ball percentage game at Bolton as the very ideological opposite of the way things should be done in East London, but it was a style of football that brought them Premier League stability, a Wembley final and even a place in Europe. Besides, despite Mark Davies's strike against Blackpool last November being possibly the best team goal of the season, it's not as if the Trotters play like Barcelona under Owen Coyle, and you don't hear much criticism at him.
Allardyce may not be West Ham fans' ideal manager, but then West Ham are not Allardyce's ideal club. Much better to let this marriage of convenience roll for as long as it benefits both parties, but it may be Big Sam who is done with West Ham first, rather than vice versa.
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QUOTE OF THE DAY: "I am extremely disappointed that I will not have the opportunity to manage Aston Villa next season. I now intend to take the next few months to concentrate on recuperating fully before I may return to football... I have been extremely touched by all of the messages I have received and by the reaction of people throughout the world of football." - Gerard Houllier announces that he will not be returning as Aston Villa manager next season due to ill health. Fulham boss Mark Hughes is favourite to replace him.
ELECTION RESULT OF THE DAY: 186-17 - FIFA president Sepp Blatter stormed to re-election in yesterday's elections. As the only name on the ballot paper, the vast majority of the 206 delegates voted him on for another four-year term despite the bribery and corruption storm swirling around the world's governing body. Sixteen other nations supported the FA's abstention, far more than was expected, but Blatter can now deal with continued allegations - such as the latest ones from former UEFA president Lennart Johannson - from the comfort of his Zurich office once more.
FOREIGN VIEW: "We are talking with Barcelona and Rossi would love to play for the club. His price-tag is between 25 million and 30 million euros. We are now waiting for news from Barca." - Federico Pastorello, the agent of Villarreal striker Giuseppe Rossi, reveals his client could be on his way to the Camp Nou.
COMING UP: Two more England players will be put up in front of the media ahead of Saturday's Euro 2012 qualifier against Switzerland, and we'll let you know just how delighted they are to be representing their country etc... In terms of live sporting action, there is live coverage of the semi-finals of the French Open kicking off at 13:00.
- Sam Allardyce
- West Ham
- Newcastle United
- Tony Fernandes