Massara meets Juve at the wrong time, if there ever was a right one [Bonus article]

Ricky Massara has been heavily praised since he joined AC Milan from Roma back in the summer of 2019. He has often gone a little bit under the radar, understandably ending up in the shadow of club legend Paolo Maldini, but his work has been recognised as of late. Especially by the industry.

The former Roma director and Maldini even shared the award for the ‘Best sporting director of the year’ at the Globe Soccer Awards a few months back. Justified, but also a bit funny since Maldini technically isn’t Milan’s sporting director. In any case, the point is his work hasn’t gone unnoticed.

Therefore, certain news that has surfaced in recent weeks is a bit annoying. Juventus are undergoing a revolution of sorts and one of the names on their wish list of potential new directors is Ricky Massara. And it seems that they are willing to offer him a significant role as well.

On Monday, SportItalia reported that Juventus even had a meeting with the director recently. A meeting that can be described as a first opportunity to sit down and talk with him. Understandably, this didn’t go down too well in the Milan headquarters but at least for now, nothing concrete has come out of it.

Given that Juve’s interest has been reported for several months now, this hasn’t exactly come as a shock. However, Massara certainly could have chosen a better time to deal with the matter, or at least declined out of respect for his current employer. Because the fact is that the team he has put together at Milan is struggling on the pitch.

If there ever was a right time, this certainly wasn’t the one. Tensions are already running high within the club as there is frustration over the results. The management is confident that Stefano Pioli and his men can turn things around these upcoming weeks, but the Champions League remains at risk and nothing is certain.

Gerry Cardinale is not watching on from afar anymore either, he has been very present over the last few months. Not just because of the stadium project, which he’s really pushing for (and he appears to be ready for that fight), but also because evaluations will need to be made at the end of the season.

Pioli can certainly be described as the first man that will come under scrutiny, there is no doubt about that, but after him comes Maldini and Massara. The club legend may have a certain protection given his heritage, but the same cannot be said for Massara and the Juventus opportunity might become all the more enticing.

Looking at it from Massara’s perspective, the opportunity is indeed an enticing one. He’s not the frontman at Milan - even if the relationship with Maldini is fantastic - and the Bianconeri are likely willing to offer him an esteemed role at the club. An experienced director to lead Juventus out of the chaos that has been.

Given the potential that Juventus have, who wouldn’t consider such a job? Maybe Maldini, but Maldini is not your normal director in the world of football. In that sense, therefore, there must be some kind of lenience on Massara. It’s not his fault that the line between loyalty and disloyalty has become so blurred that we barely see it anymore.

With the ‘in his defence’ talk out of the way, though, he could have picked a better time and at least made sure it wouldn’t get out to the media. The latter is not exactly hard these days either. It’s possible, of course, that the meeting took place a few weeks back (even months) and it got reported by the media now because Milan are in such a delicate period. But in any case, the whole of 2023 has been poor and not the perfect time for a meeting with a rival.

It should be noted that Massara is under contract until 2024, and Juve would likely have to pay Milan to get him before that. Let’s see what happens, but it’s a situation that should be monitored closely and we will make sure to have you covered on that.

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