He has just guided Juve into the Champions League final. But he could have been at Elland Road, if Massimo Cellino had got his way.
The Champions League final has been decided, with Barcelona set to take on Juventus in Berlin later this month for the title of best team in Europe.
Barcelona are always expected to make it this far, but Juve have been perennial underachievers in the competition in recent times.
Now they have made it, Juve fans are hoping they can go all the way.
The man who has finally taken them over this hump is Massimiliano Allegri. The Italian has put behind him a disappointing end to his time as boss of AC Milan and is now looking at a potential treble for the Bianconeri.
Yet, In January 2014, he was rejecting Leeds United's approach for the manager job.
Allegri had previously worked under Leeds owner Massimo Cellino at Cagliari and, according to Football Italia, Cellino wanted to replace Brian McDermott with Allegri at Leeds.
He turned down the offer and since then Leeds have gone through McDermott, Dave Hockaday, Darko Milanic and now have Neil Redfearn on hot coals in the driving seat.
Allegri took the Juventus job in the summer and has gone on to perform exceptional feats in Turin.
Who knows what he might have done for Leeds United? One thing for sure though, Elland Road is probably a tougher place to manager at the moment than the Juventus Stadium.