Who in the World is Ricky Massara?

Milan announced last week that they hired their second choice Sporting Director, Frederic Massara. While he had been rumored to be chosen after their first choice decided to stay at Lazio, the reaction from fans was not very passionate. That is likely because most of us have no idea who he is.

He can hold a phone, that is great news

Massara played football as a striker, mostly in Serie B and C. Then he tried his hand at coaching, taking three different assistant coach jobs for Benevento, Pescara, and Martina over a two year period. That was apparently even less impressive than his playing career.

In 2008, he moved to administrative roles, working with Sabatini. First he was at Palermo, then he followed him to Roma in 2011. Meanwhile, he had been studying to become a Sporting Director. Milan’s official club statement pointed out that he scored a perfect 110 out of 110 on his test to become a Sporting Director, which only indicates that he is intelligent, not necessarily that he has what it takes to scout and acquire players, keep personal relationships with people, etc. – the things that really matter to be a good Sporting Director.

Stepping out of Sabatini's shadow

In 2011, when Massara followed Sabatini to Roma, he subsequently spent five and a half years working beneath his mento\. When Sabatini left Roma in October of 2016, Massara was promoted to Sporting Director, replacing him. However, Massara also left Roma at the end of that season to work under Sabatini once again as the coordinator of sporting activity for both Inter and Jiangsu Suning. That lasted less than a season, until March of 2018. So last June, he returned to Roma to work with Monchi, and was given the random title of “General Secretary.” When Monchi left Roma this past March, Massara was once again appointed as their Sporting Director. However he left Roma again, this time by mutual consent, after only two months in that position. That freed him up to accept the Milan position.

So what does all of this say about Massara? Who is this guy, really? Well we know he was barely an average striker, apparently a below average assistant coach, and that he stalks his mentor, but otherwise can’t seem to hold onto a job, at least not as Sporting Director. The only clubs he’s worked for have ridiculous transfer markets. Sure, they buy good players, but they also sell them in such a haphazard way as to impact their teams very negatively on the pitch. Also, both Inter and Roma have had serious FFP sanctions, so that’s kind of perfect.

He likes long walks outdoors with his mentors

The guy is obviously smart. So all of our management are very intelligent, but can they do their jobs? He has just over a year of actual experience as a Sporting Director, and while his other positions have allowed him to work alongside Sporting Directors, this is very different. Milan is not like Roma or Inter, we actually have the capacity and desire to win, not cheat or steal or finish second or third all of the time. Massara is incredibly inexperienced for where Milan are at right now and where we need to be.

I don’t know if Massara was the only potential Sporting Director left, the bottom of the bin, or Milan's only option. I definitely know he wasn’t Milan’s first choice. But it seems like if we are rebuilding and desperately need to get back to Champions League, this would be the one position where you would want someone with more experience. And while he has varied experiences at three different clubs, it’s hard to believe he’s prepared to be the Sporting Director we need, especially at this point in our rebuilding.

Everyone is inexperienced at Milan, but at least these guys are footballing legends

Between Maldini, Boban, and now Massara, Milan’s new management is looking more like a Mensa braintrust than a club’s technical area. Maldini and Boban at least have remarkable football careers to draw from… not only as experience but as a source of immense respect within the footballing community and beyond. They have vast networks of relationships within the footballing community due to having played at the highest level for so many years and remained close to football since retiring. But Massara is largely unremarkable to date, whether it be from his playing career, assistant coaching career, or even his penchant for following Sabatini around. We can only hope that his work at this job changes all of that. But for now, even prospective players are asking “Who in the world is Ricky Massara?”

This post inspired by the music of The Who