For a man raised in an era when winning the FA Cup was the common and unquestioned dream of everyone in the English game, it was hard to fathom. How could a team like his, one with realistic ambitions to boot, land a home tie against the holders and yet play to a stadium not even half full?
Those who did turn up at the Reebok Stadium on Saturday evening were as appreciative as Sam Allardyce when Stelios Giannakopoulos maintained his scoring habit against Arsenal to complete a dismal week for Arsène Wenger's team, whose quest for domestic silverware ended on two fronts. But in rounding on those who failed to appreciate the magnitude of the occasion, the Bolton manager was failing to appreciate the part he has played - albeit unintentionally - in the inevitable decline of a once unparalleled institution.
The real culprits are not the television companies, which demand that ties be played at inconvenient times, but the managers who unapologetically - unavoidably, they would argue - prioritise.
Wenger, like Sir Alex Ferguson, makes no secret of it. Behind the Premiership and the Champions' League, the FA Cup at best is number three. For Bolton, nowadays, the opposite is true.
"I would sooner get to the FA Cup final than finish in fourth spot in the Premiership," Allardyce said. "Because it goes on everyone's CV that you have got to an FA Cup final and for this club to win it would be more important. When the next round comes around we will have most of our players back from African Nations' Cup duty."
Hence the 11 players he sent out, from a squad as depleted as their opponents', were as strong as he could muster, in contrast to Arsenal, for whom the risks that might have been taken in fielding Thierry Henry, Robert Pires, Lauren or Dennis Bergkamp were not justified by the status of the match.
Yet two years ago, with a smaller, poorer squad than he has now and considerable financial pressure to avoid relegation, Allardyce kept his most important players under wraps for a replay against Tranmere Rovers, suffering an embarrassing defeat as a consequence.
The message to the public, however, was the same one that Wenger reinforced on Saturday, that the total commitment from both teams that was once the essence of the FA Cup is no longer guaranteed.
At least there is no doubting Bolton's towards this year's competition. "Winning the Cup is a reachable goal for us," Allardyce said. "And having beaten Arsenal tells everybody that we might be capable, if the draw is kind to us."
Ironically, for all the inexperience of Wenger's side, which included two teenagers in the back four among seven players under 22, Arsenal did compete, much more effectively than they had on the same ground in December, when Premiership points were tamely surrendered in the face of Bolton's physical power.
"We did enough to have won by three clear goals and can take a lot of positives from the game," Wenger said. "It showed we can battle away from home. I had said before that we cannot go on letting teams bully us and we had a great response today. It can inspire us to aim for a decent position in the Premiership. It is important we do not feel sorry for ourselves. We must take positives from our defeat and keep going."
Abou Diaby, the 19-year-old earmarked as the new Patrick Vieira, impressed his manager in particular on only his third appearance, although Wenger's enthusiasm for the way he "put his foot in" was not shared by Ivan Campo, who suffered a broken foot for the second time this season as a result of a challenge for which the former Auxerre midfielder was fortunate only to be booked.
Wenger's contention that Bolton scored from their only clear chance was debatable, although the outswinging cross from Ricardo Gardner that a diving Giannakopoulos met to head home the decisive goal may be justifiably called the only moment of real quality. The stayaways did not miss a lot.
Goal: Giannakopoulos (84) 1-0.
Bolton Wanderers (4-4-2): Jaaskelainen; O'Brien, Ben Haim, N'Gotty, Gardner; Nolan, Campo (Vaz Te, 54), Nakata, Giannakopoulos (Hunt, 89); Davies, Borgetti (Jansen, 73). Substitutes not used: Walker (gk), Fojut.
Arsenal (4-1-4-1): Almunia; Gilbert, Campbell, Djourou, Senderos; Diaby; Hleb, Ljungberg, Flamini, Reyes; Van Persie. Substitutes not used: Poom (gk), Larsson, Bendtner, Lupoli, Muamba.
Referee: M Dean (Wirral).
Booked: Bolton Davies; Arsenal Reyes, Diaby, Senderos, Van Persie, Gilbert.
Man of the match: Gardner.
Attendance: 13,326.Reuse content