Arsene Wenger’s time at Arsenal will go down as one of the finest managerial reins of an English club, and second to only Sir Alex Ferguson in the Premier League era.

Winning three league titles and claiming seven FA Cup trophies go a long way to cementing his legend in the English game, however, his record in the transfer market, especially over his first decade in charge, shouldn’t be overlooked.

How much did Arsenal sign Anelka for?

The likes of Thierry Henry, Marc Overmars, and Sol Campbell all arrived at Highbury during the Frenchman’s tenure and turned the club from underachievers to arguably the best club side the Premier League has ever seen, with Henry and Overmars generating the club a major profit in the process.

However, it was Nicolas Anelka, who cost the North London side just £500k back in 1997 having joined from Paris Saint-Germain, that would become one of his shrewdest investments.

Was Anelka Wenger’s finest Arsenal signing?

The talented striker was just 17 when he swapped Paris for London and despite his limitless potential, his fiery nature meant he was just as likely to fly off the handle than to score in front of the Highbury crowd, and controlling this was Wenger’s main challenge.

The Frenchman netted 28 goals in 87 appearances for the Gunners, yet, considering he moved countries at such a young age, it is a fantastic return and he played an integral part in securing the first double under Wenger in 1997/1998, scoring six and goals and grabbing a further half a dozen assists.

With Arsenal ready to burst into the stratosphere and create a side that could conquer Europe, Real Madrid came calling for Anelka and a fee of £22.3m was agreed between the two clubs, marking a staggering 346% increase on the original £500k Wenger paid.

Despite his early promise, Anelka never really lived up to the hype surrounding his outstanding early period and it wasn’t until his spell at Chelsea that he started receiving the praise he should have gotten years before, with Phil McNulty describing him as a “match-winner” back in 2009.

Wenger certainly struck gold on the 69-cap striker – who also won the European Championship with France in 2000 – and although the club made a staggering profit on the player, the legendary manager may have wondered what might have been had the striker remained in London. Henry 2.0 anyone?