#2 Arsene Wenger (Monaco, Arsenal)
Notwithstanding Arsenal’s recent decade-long slide (although one punctuated by three FA Cup winners), Arsène Wenger’s brilliance had already been proven at that point. All three Premier League championships were won with dazzling flair and on a very little budget, putting some of Europe’s biggest spenders to disgrace.
Wenger was instrumental in Arsenal’s modernization, although his results in Europe were inconsistent. There were impressive wins, such as a 5-1 thrashing of Inter and a victory against Real Madrid at the Bernabéu, but never a championship season.
Under Wenger’s guidance, Arsenal advanced to the UEFA Cup final in 2000 (when they lost on penalty kicks to Galatasaray) and the club’s first Champions League final in 2006. (a 2-1 loss to Barcelona). A manager with more Champions League victories than anybody save Alex Ferguson and Carlo Ancelotti came close but fell short.