Tears for the clown Prince of Pompey

Amid the many tattoos on Kevin-Prince Boateng's body are two jokers. "One is smiling and the other crying. It means laugh now, cry later," he once explained.

For the Ghanaian-German the motto has come all too true during the later stages of Portsmouth's FA Cup run. The laughter came after the semi-final when his penalty completed Portsmouth's improbable defeat of Tottenham, his former club. The tears came yesterday as, in the turning point of the match, he fluffed a spot-kick.

"I'll never get bored of watching it go in," he said after his successful conversion against Tottenham. It is safe to assume he will not want to watch yesterday's penalty again. His weak effort was too close to Petr Cech.

It is very possible that Chelsea may have come back to win even had Boateng scored. There was more than half an hour remaining and the champions are a very powerful side. But it is just as possible that they would not have. Mentally they would certainly have feared that fate had decreed Portsmouth would sign off this calamitous season with a remarkable triumph, while Portsmouth would have thought it was written, having seen Chelsea hit the woodwork five times already.

Instead, within three minutes, Didier Drogba scored and Chelsea were on their way. The combative Michael Brown tried to lift his team-mates, and they did have some fleeting glimpses of an equaliser, but the belief had drained from them. Boateng did not even finish the match. The ankle injury that made him doubtful probably forced him off, but his head was gone in any case.

It had been an eventful final for the 23-year-old. He had already put Michael Ballack out of the game with an ill-judged tackle that prompted immediate concern from the German media contingent as to their captain's fitness for the World Cup. The incident was unfortunate considering Boateng has represented Germany at under-21 level, but he is currently awaiting Fifa permission to switch nationality to the country of his birth. Last week he was named in Ghana's provisional squad and, if Fifa assent, could be lining up for Ghana against Germany, and Ballack (if fit), in Johannesburg on 23 June.

Boateng is a talented player, but there are doubts about his ability to realise that talent consistently. On the sales list Portsmouth circulated last week he was the highest-priced player at £5 million. Pompey paid £4m for him in August, two years after Spurs bought him from Hertha Berlin for £5.4m.

He never flourished at White Hart Lane but at Portsmouth has applied his evident technical gifts more regularly. He has also shown mental courage. He missed another penalty, at Stoke, in November. The match was goalless at the time; Stoke won 1-0 and Paul Hart was sacked as Pompey's manager the next day. Yet when, the following week, Portsmouth were awarded a penalty at home to Manchester United in Avram Grant's first match as manager, with United one up, Boateng stepped up to take the kick, and scored.

It is to be hoped he comes back as bravely from yesterday's failure. It will not be easy; he was inconsolable at the end, and the knowledge that he could have put Portsmouth on the way to a barely believable success will never leave him. But he will almost certainly be at a new club next season, which will help. Boateng will be leaving, along with most of his team-mates, because of the club's abject financial mismanagement. Before the match the man who oversaw their slide into administration, the former chief executive Peter Storrie, had described fans who criticised his stewardship as doing so out of "ignorance". Storrie paid himself £1.2m in wages, pension payments and bonuses in 2008-09, including win bonuses for on-field results achieved by the players, as the club built up a £130m debt mountain.

"I'll always be known as the chief executive of the first PL club to go into administration and that's very unfair, but that's the football world," he said.

"For whatever part I've played, I [say sorry to those owed money], but I am an employee. The club was run by individuals and they dictate what they want to do. I had to implement that, and because I was the focal point of the club I received the criticism. I accept the criticism, I understand there'll be a lot of people saying 'good riddance', but a lot of it is down to ignorance."

Storrie, who said he did not quit (and walk away from his salary) because he had been advised it "would be a disaster for the club", remains on the payroll as consultant, advising the administrator, Andrew Andronikou, on transfers. Storrie indicated he would like to stay on after the club is sold but accepted that was unlikely.

Final facts and figures

Wembley penalty misses:

John Aldridge for Liverpool v Wimbledon, 1988

Gary Lineker for Tottenham v Nottingham Forest, 1991

(Paul Scholes missed in penalty shoot-out in 2005 final between Arsenal and Man Utd at Cardiff; Charlie Wallace missed for Aston Villa v Sunderland in 1913 but the game was at Crystal Palace).

Wood you believe it? Chelsea hit the woodwork five times in the first half yesterday:

12 minutes Frank Lampard's fierce shot hits the post

26 minutes Salomon Kalou misses a sitter and hits bar from four yards

29 minutes John Terry's looping header comes back off the bar

38 minutes Didier Drogba's swerving free-kick is tipped on to the bar and doesn't cross the line

41 minutes: Drogba gets the ball past David James but it clips the post

Six of the best for Ashley Ashley Cole now holds the record for most FA Cup final wins (six – Arsenal (2002, 2003, 2005) and Chelsea (2007, 2009, 2010).