It took two years to come full circle. Another final, another defeat and, in all probability, another swift exit. Penalties continue to pain him, with Kevin-Prince Boateng emulating John Terry in unwanted fashion but while Avram Grant remains a runner-up, this was a setback with a difference. He has had a makeover.
He is an unlikely hero, an essentially undemonstrative character whose habit of mumbling runs contrary to the image of the charismatic managerial mastermind and who appeared the antidote to the self-publicist who perfected that role.
At Chelsea, he was defined by who he was not: not the Special One, who preceded him, or the World Cup-winning one, Luiz Felipe Scolari, who replaced him, or the international alchemist, Guus Hiddink, who took over from him, or the Double-winning apotheosis of calm, Carlo Ancelotti, who is the current incumbent.
In Hampshire, he has found his identity. Among the banners brought by the vocal Portsmouth fans was one featuring the image of Grant and his words: "you'll never break our spirit". Like his on-pitch speech after the final home game of the season against Wolves, it had echoes of Mel Gibson in Braveheart; this was Grant the improbable freedom fighter.
"Sometimes you need to show you will not give up," he said. "You cannot even imagine what has happened at Portsmouth this year. This is bigger than you think. It was a very difficult season. It's a season that I will not forget. I won a lot of games in my life but this, this was unbelievable. We played against all odds."
The underdog had a chance to prosper in the FA Cup final. For Grant, the pivotal moment contained unfortunate reminders of his previous final. In Moscow in 2008, Terry slipped and missed from 12 yards; at Wembley in 2010, Boateng's spot-kick lacked the required pace or power and was saved by Petr Cech. Three minutes later, Chelsea led.
"Next time I will take the penalty," insisted Grant, dryly. This time, at least, there is honour in finishing second. There wasn't when Jose Mourinho's surprise successor was propelled into the elite of the global game in September 2007. Now he has joined Sir Alex Ferguson and Arsene Wenger in a select band to have lost finals of the Champions League, the FA Cup and the Carling Cup as well as finishing second in the Premier League.
"This is the last thing I am thinking about," added Grant. "The future of the club is more important that my future. It's a good club, if you see the fans today, they are great fans. The team have identity now."
That is an achievement. Grant may have inherited a side at Stamford Bridge that was sufficiently well drilled to barely require a manager. At Fratton Park, he was denied such luxury. He cannot, though, be deprived of the credit, for galvanising and rallying a group of players whose futures lie elsewhere yet whose commitment has been apparent throughout this cup run.
The defiance of Aaron Mokoena, twice blocking shots from Didier Drogba in the space of seconds, was telling. If, however, Portsmouth have claimed, often justifiably, that luck has deserted them this season, it made an emphatic return as the woodwork thwarted Chelsea five times in the first half alone.
In that respect, it was one of Grant's less credible claims that Pompey merited better. Nor, indeed, did a manager who launched into another impassioned argument against Portsmouth's exclusion from next season's Europa League support his own case by entering Wembley in the company of Peter Storrie, the former chief executive who is culpable for their descent into administration.
A persecution complex is often unedifying, but much can be determined from actions in adversity: Grant has acquitted himself admirably. Against a superior side, his team were tactically excellent, deploying the pace of Boateng and Aruna Dindane on either flank to give striker Frederic Piquionne support on the counter-attack and looking to break at speed.
For Grant, it brought a familiar feeling on a showpiece occasion. He came within a whisker of a holy grail two years ago and now the newcomer at Stamford Bridge has a Double. The Israeli was consoled by Ancelotti on the final whistle. He pronounced himself "proud but sad". They are appropriate adjectives for the efforts of the manager and his players, though not Peter Storrie and his ilk. From the wreckage of a scarred season, Grant has emerged an enhanced figure.