It's a question doing the rounds in Italy right now. Following an admittedly excellent season at Bologna, is it time for one of Serie A's biggest clubs to give Alessandro Diamanti the chance to shine?
This writer's honest answer would be a swift and simple "no," but since that doesn't make for very interesting reading, let's elaborate.
He's an excellent crosser of the ball and a talented free-kick taker. He has an eye for the goal and the intelligence and creativity to see a chance when few others would. And he's flexible, having featured in the centre, on the wing and up front for the Rossoblu.
But—and it's a big but—he's 30 in a league that's turning more and more to young talent.
This is a player who found chances limited at West Ham, a mid-tier club that was relegated not long after it had offloaded the Italian, thinking him surplus to requirements.
After an ultimately disappointing spell in London, he moved back to Serie A with Brescia. They were relegated the following summer, but in fairness to Diamanti, he had an impressive campaign. His consistent performances and six goals earned him a move to Bologna and a call-up to the Italy squad under Cesare Prandelli.
And that's the thing. Saying he's a poor fit for Milan is not to diminish the player's quality. Diamanti has formed a solid partnership with the rest of the squad at Bologna, especially Alberto Gilardino. Long may it continue.
The reason he's the wrong man for Milan is that like his strike partner, his charms are such that a big move could be justified. But like Gilardino, he might just have found his level.
Gilardino knows what it's like to earn a move to the San Siro, only to be ditched when the next bright young thing comes along.
His experience should serve as a cautionary tale for Diamanti, because while Gila had the years and the energy left to rebuild his career at Fiorentina and then Bologna, realistically Diamanti's time at the top is limited. A bad move now, and he'll retire in obscurity.
Diamanti's a likeable player. And after both Robinho and Kevin-Prince Boateng had such poor seasons for the Rossoneri, Max Allegri needs to shake things up in the attacking midfield department, that much is clear.
But €10 million for a player with few years left and nothing but lower-level experience looks like a bad bit of business for a club keen to build around the youthful promise of Mario Balotelli, Stephan El Shaarawy, M'Baye Niang and Mattia De Sciglio.
He's had a good season. But it should be taken in context.
He's a big fish in a relatively small pond, and even then he managed seven goals and the same amount of assists in a league where his team finished 13th, just above three teams who were all docked points.
Diamanti can impress for Bologna, but can he do it in the Champions League for Milan? Has he really improved that much since his time at West Ham?
Italian football is full of players who shine at smaller clubs. But Milan, Juventus and Inter aren't rushing out to sign German Denis and Fabrizio Miccoli.
For their own sake, and for that of the player, let's hope Milan realise Diamanti's limitations before they make what would be a bad move for both parties.