Twenty years ago, he signed Ji-sung Park from PSV Eindhoven and later, reflecting on the impact of the South Korean, confessed leaving him out of the matchday squad for the 2008 Champions League final, against Chelsea in Moscow, was one of the hardest, and harshest, choices he took while in charge.
But there were plenty more that will have had him agonising at the time and wondering if he was following the right path.
Not just excluding players from big matches but also discarding them altogether, agreeing to sell some of the sport's biggest names in moves that puzzled and angered some supporters.