Leonardo, whose brilliant playing career made him a rossoneri icon is, at best, a hesitant coach. He was persuaded to take the AC Milan managerial reins after Carlo Ancelotti's 2009 sacking and was replaced at the end of that season as his relationship with club owner Silvio Berlusconi became progressively more unworkable. After six months out of the game he resurfaced as Inter Milan's boss replacing the remarkably unpopular Rafael Benitez. Inter, fourteen points behind league-leading red-half rivals AC, promptly went on a tremendous run to the point where April's Fashion City Derby became the season's deciding game.
Under new coach Massimiliano Allegri, AC Milan were triumphant and Inter Milan settled uncomfortably into second place in Serie A. The nerazzuri's title streak died at five. Leonardo, whose coaching philosophy could be best described as rolling the ball out and saying "Go play", empowered that turnaround either by shrewd assessments of his players' moods or by sheer good fortune. However it was accomplished, large questions remain as to his coaching prowess and even his suitability to such an everyday, hand-on role. Rumours persist that he has no great love for the role of manager and even in the mid term would prefer a boardroom position.
Perhaps this is the rare occasion where nice guys actually do finish first. Leonardo presents exceedingly well: dapper, articulate and friendly. The move to PSG presents the opportunity to hone his skills, revisit past glories or maybe just an escape from the relentless baking heat of the Italian media kitchen. Perhaps he felt club expectations were too high in the wake of opponents strengthening. Having said that, however, PSG's new Qatari owners should be very aware of what they will be getting: style with little proven substance.
For someone who has shown no great affinity for the work, reportedly has designs on higher and less stressful offices and isn't a relentless self-promoter, Leonardo has the happy ability of falling on his feet; his skills on the training track overshadowed by his incredible talent for dealing with almost despotic club owners Berlusconi and Moratti. PSG, one of France's most storied clubs - and where he played for two years from 1996 - can only speculate as to what they are getting beyond an urbane, handsome spokesman.
Whether Leonardo's attacking football - which promotes player enjoyment - last season was a reaction to Benitez's staid gameplan or the first manifestations of an easygoing coaching style is amusingly unanswerable. Whether it was genius or luck, his mindset and tactical nous still need proving.
Moratti's satisfaction with his former sideline boss is unknown. Whether this is a blow to his plans for the side really comes down to his opinions as to Leonardo's ability, a situation where has more information with which to judge than we in the public. What is, however, apparent, is the search for a replacement, which given the dearth of quality candidates could become one of summer's football tiresome constants.