A few eyebrows were raised when Arsenal were linked with Marc Overmars in the summer of 1997. No one doubted the Dutchman's talent - he was one of the finest wingers in world football - but his well-documented injuries were a concern.
Overmars was a diminutive wide man in the young Ajax side which swept past Milan to win the European Cup in 1995. However a serious knee problem, suffered the following year, ruled him out of Euro '96 and cast doubt on the Dutch flyer's long-term future.
Wenger decided it was a risk worth taking and, not for the last time, the Frenchman's judgement was impeccable. Overmars took time to find full throttle but - once a minor foot injury had eased - he took English football by storm.
Overmars became a vital cog in the Arsenal machine which brought the Double back to Highbury in Wenger's first full season. That 1998 vintage had the power of Petit and Vieira and the guile of Bergkamp. Now the blistering pace of Overmars made them an awesome counter-attacking force.
Bergkamp was probably the main man but Overmars was his ultimate wing man. Right backs all across the country were given a torrid time as Overmars ran at them and jinked inside or sprinted onto weighted passes inside the full back from the likes of Petit and Bergkamp.
Defenders knew that, given a yard start, Overmars would not be caught, and that avenue was a potent weapon for Arsenal in Wenger's first Double year. Overmars followed braces against Leeds and West Ham with a vital strike at Barnsley as silverware loomed large.
And when it came to the big occasion, Overmars rarely failed to deliver. He was the outstanding performer at Old Trafford in March 1998 as Arsenal took the game to Manchester United and emerged with a 1-0 win. Overmars netted the vital goal after threatening to score on numerous occasions; the result swung the title balance in Arsenal's favour.
The title clincher against Everton in May was no different. Overmars raced away to earn a 2-0 lead before half-time and his superb individual strike in the second half - showing skill, pace and a deadly finish - effectively confirmed that the title belonged to Arsenal.
The FA Cup Final painted a similar picture. After a cagey opening, Overmars' pace made the difference. He burst inside his marker in the left channel and raced onto Petit's lofted pass before beating Shay Given. Arsenal were on their way again; an hour or so later the Double would be theirs.
Overmars had enjoyed a vintage debut season - and not many overseas imports can say that. However, that was as good as it got for the Dutch winger. Injuries diluted his impact over the next two campaigns and, after a handy 41 goals in 142 appearances, Overmars moved on in the summer of 2000.
By now, Arsenal fans were desperate to keep him but, once again, Wenger judged his transfer dealing perfectly. He received top dollar from Barcelona as Overmars became the most expensive Dutch player of all time - but the flying winger never scaled his previous heights again.