Perhaps no player has ever looked quite so much as though he ought to be playing for Monaco as Dimitar Berbatov. Forget the reality of an under-supported club sustained by Russian money and tax breaks, playing on top of a car-park; if Monaco really were a club representing the playboys of the Côte d’Azur, all yachts and deck-shoes and meaningful glances over the champagne cocktails, Berbatov would fit right in. Throughout his career, his demeanour has been of a mysterious loner in a white dinner jacket leaving a casino in the early hours, his bow-tie long since undone.

And yet, fitting as it seems that he should end up at Monaco, this is not a culmination. Indeed, it may not even be the gentle drift into obsolescence players are entitled to in their mid-thirties. You wonder how fulfilled Berbatov actually feels at 34 as he contemplates the autumn of his career. Better, perhaps, to be trotting around in front of six or seven thousand in the French league and playing, still, in the last 16 of the Champions League than scrapping against relegation in the Premier League, but there has always been an air of sadness about Berbatov.

Coaches who worked with him in his native Blagoevgrad say he was by no means the most talented player in the town but he was the hardest-working, a surprising inversion to his popular image. Since Hristo Stoichkov had given him a signed pennant when CSKA Sofia came to play Pirin, the third-division side for whom his father featured, in the Bulgarian Cup, Berbatov had dreamed of playing for the club. In 1998, aged 17, he achieved his ambition.

Berbatov loved the club: when his mother, the formidable Margherita, unexpectedly visited the dormitory during a holiday, she saw him hiding a pad of paper on which he’d been doodling under the bedclothes. She grabbed it, expecting to see the name of a girl he was dreaming of; what he’d actually drawn was the CSKA badge. But the club rejected him, fans turning on him after a string of missed chances in a derby against Levski. When he received a death threat after a poor performance in the opening game of the 2000-01 season, against Litex, he considered quitting football, but instead left Bulgaria, moving to Bayer Leverkusen.

Berbatov’s career from then can be seen as a cold advance up the career ladder. He maintained the cool exterior of Robert De Niro, whose poster he’d had on his wall before replacing it with one of Alan Shearer, and never allowed himself to get too attached. Football was a profession, and he treated clubs as other professionals would regard their employers.

Only Berbatov knows how satisfied the approach has left him, but his medal haul, for a player so talented, is meagre: a Bulgarian Cup with CSKA, a League Cup with Tottenham, two league titles and a League Cup with Manchester United. He may have won Bulgarian Footballer of the Year a record seven times, but even his relationship with the national side ended in frustration and retirement at 29. The clinical approach has brought a solid career, but not a huge amount of glory.

And the powers are fading.

Berbatov scored six goals in nine starts and three substitute appearances after joining Monaco from Fulham last January, and has scored six times in sixteen starts this season, making him the club’s top scorer. Stats from whoscored.com show assists are down, as are pass completion, key passes and how often he is fouled. He is winning more aerials this season, suggesting perhaps an unlikely parallel with late-era Shearer.

But the fact is that his languidness cannot disguise his diminishing sharpness and there has been an uncharacteristic petulance about him at times of late, most notably when he poked Corentin Tolisso of Lyon in the eye at a set-piece at the beginning of February. Then again, a certain distractedness is perhaps understandable after his brother, Assen, was given a 14-month suspended jail sentence in January for selling cocaine.

And there were some hints in the first hour of the 1-0 win over Nice at the weekend of Berbatov edging into form, with the coach Leonardo Jardim praising his “intensity” and “tactical awareness” as Monaco overcame the dismissal of the centre-back Aymen Abdennour just before half-time; nonetheless, Berbatov was taken off after 58 minutes.

Glory in football isn’t measured only in medals, of course, but for those who have plotted their careers as ruthlessly as Berbatov, that has (alongside money) to be the major factor. There’s the possibility of a Coupe de France – Monaco face Paris St-Germain in the quarter-final next month – but at this stage of his career, Berbatov realistically can do little more than embroider the legend, add a few more flourishes, moments of louche genius to our memories.

A goal at Arsenal, passage to the Champions League quarter-final, would do that, but the legend, perhaps, should already have more substance.