Definitely, Juventus considered as a big rival on the pitch, but the relationship outside from the game (e.g. mercato) between Milan and Juventus sometimes shows the contradictions, just like there was no rivalry.

In the old days, the transfer between rivals often occurs. The transfer like Giuseppe Meazza, Sandro Salvadore or Aldo Serena. In fact, since the 90’s the direct transfer with decent players which means strengthen the rival in an opposite, were frequently rare. However, this thing seems only applied clearly in Milan-Inter connection only. Direct move between Milan and Inter players with potential or reputable names was something rare.

We knews Francesco Coco, Giuseppe Favalli, Sulley Muntari or Giampaolo Pazzini-Antonio Cassano swap deal. However, the above Milan-Inter names aren’t comparable due to the Milan-Juve direct transfer like Meazza, Serena, Baggio, Inzaghi or Pirlo.

There were only a few direct transfers between Milan and Internationale or Internationale and Juventus, but what rises from Milan and Juventus relation sound the slight bit different. There are many direct transfers between Rossoneri and Bianconeri, either those who have high profile names or just wreck’s players.

It clearly that Milan and Juventus rivalry in mercato, isn’t so bad comparing when both teams face each other in the match. That’s why between Milan and Juventus connection, the direct transfer often happened. Even though, in that direct transfer, both clubs don’t inevitably obtain the result that they want.

Roberto Baggio

One of the Ballon d’Or bound who play for Milan was Roberto Baggio. The world knew precisely about his essential greatness as a talented footballer. Technically gifted, goal-eye, uniqueness, a big game player (despite World Cup 94 failure) and so many attributes rightfully belong to the Divine Ponytail. Although he comfortably reached peak performances when plays for Juventus (1990-95), but slightly decline and potential Alessandro Del Piero arrival made Baggio transferred to Milan in the end.

Roberto Baggio.

Baggio starts to struggle his life in Milan with injuries. However, he scored 19 goals and merely manage 67 in two seasons (1995/96-1996/97). Baggio contributed fairly on Milan winning Serie A title in 1995/96. However, due to the changes in the managerial sector and considered finished up, he was moved to Bologna in 1998. Though not underperformed and slightly showing his elite class, Baggio football carrier in Milan wasn’t special either.

Edgar Davids

Arrived in Milanello as a prominent youngster from Ajax, Edgar Davids has failed to show his best in 1996/97 season. Then, after just one season in Milan, Suriname-born defensive midfielder sold to Juventus and established a place in Turin. It’s true that most of us dominantly remind this iconic dreadlock and outstanding player in and black shirt, not in red and black one.

Shameful, Milan lost Davids gear talent to Juventus in summer 1997. But, it takes no longer to properly find out his potential replacement in Milan, after Gennaro Gattuso joining in 1999’s summer for 8 million euros.

Edgar Davids photo during his time at AC Milan.

Typically, both players have similar attributes. The defensive midfielder with ball-winner intent, destroyer opponent, and tireless lung. But the destiny has been distinguishing both players. For Milan fans; Davids as the forgotten one, while Gattuso as the legend one.

Filippo Inzaghi

We should thank this one for Juventus. Actually, Filippo Inzaghi was their main striker since Juventus bought him in 1997/98 from Atalanta. He created “a real deal” partnership alongside with Alessandro Del Piero and Zinedine Zidane. The best tridente combinations brought Juventus to the Champions League final seasons 1997/98, which eventually lost against Madrid.

Despise by Juventus, but being a legendary striker in Milan: Filippo Inzaghi.

Despite showing the natural sharpness and scoring a lot of goals, Filippo Inzaghi didn’t really need by Juventus. They are instead signing David Trezeguet in 2000/01 to created internal competition toward Inzaghi.

Spent the season in share-time with a competitor and that disappearing collaboration with Del Piero, meant it was time to go for Pippo. Then in 2001/02, Milan came and offering 36 million euro (include Cristian Zenoni) to Juventus. We knew the rest is the historical legacy after Filippo “Pippo” Inzaghi joined Milan until his retirement in 2012.

Christian Abbiati

This was undoubtedly a real evidence why Milan and Juventus’s relationships in mercato considerably are quite good. Once, Gianluigi Buffon suffered long-term injury after colliding with Kaka in preseason Trofeo Luigi Berlusconi in 2005. Then, Milan had offered adequate compensation with Christian Abbiati on loan to Juventus for 2005/06 season.

Milan’s top-class action in Christian Abbiati loaned to Juventus.

Milan had no problem at all because of Abbiati at the current time only a backup goalkeeper for the first choice, Nelson Dida. Meanwhile, Juventus acquired a decent goalie such as Abbiati in free for one season during Buffon recovery from dislocated injury. This was undoubtedly a real win-win solution deal for both clubs.

Andrea Pirlo

It was one of the most bitter direct transfer for Milan when saw Andrea Pirlo sign for Juventus. We knew precisely Andrea Pirlo. He was one of the best deep-lying playmaker or regista ever to play for football. The smartness, vision, technique, and his passing were superb. Since his orchestra in Milan started from 2001/02, Pirlo leads Milan to glorious time with two Champions League trophies and two Serie A titles then.

Andrea Pirlo. Free transfer from Milan to Juventus in 2011.

Unfortunately, a wrong decision made by Milan Management in summer 2011 by not giving him a contract extension. Milan thought Pirlo ended up, instead, Allegri had more suitable regista named as Mark Van Bommel to his tactical profile. Affirmatively, Juventus promptly signed Pirlo on a free transfer which was in another hand, Milan let them to dominating Serie A by intelligent Pirlo guidance, even after Allegri reign at Juventus. While Milan, until today never found again top class deep-lying playmaker like Andrea Pirlo.

Mattia De Sciglio

Mattia De Sciglio was Milan primavera product. Made with proud being a part of Rossoneri youth system which also creating football such as Franco Baresi and Paolo Maldini. He was inherited several aspects to be Red and Black jersey legend. He was born on Milan, rise up in young age (19th), plays in defense just like Franco or Paolo, and earn captain role in 2016.

Milan-born, primavera boy, and former captain. But, Mattia De Sciglio signed for Juventus in 2017.

It seems all to be the perfect life for him. But, several injuries hitting him and impacted his performances then. De Sciglio earn much criticism from fans for his performance (especially in 2016/17) and pushing for a move to Juventus last season. It was shameful considering he was Milan primavera boy and touted as nuovo bandiera but departed from Milan just for short- time glory in a rival club. Fortunately, Milan has Davide Calabria who is better than De Sciglio either.

Leonardo Bonucci

The most complicate Milan and Juve direct transfer ever. After “that night in Cardiff” in the year 2017, Juventus suffered disharmonies in their squad. Heavy rumor to like reliable issues appeared toward in the case. It proved with Daniel Alves and Leonardo Bonucci exits from Juventus last season. Indeed, those two, mentioned in the raw issues on Juventus Champions League final half-time break.

Leonardo Bonucci with Milan captain’s arm band.

Suddenly in summer 2017, Bonucci leave Juventus for Milan. For Rossoneri fans, maybe it was their sweetest moment in the previous summer. However, Bonucci, who later became Milan captain in 2017/18, turn out being “a snake” after pursuing chance for Juventus return this season. In Bonucci return term, this agenda worth to be called a disgrace not only by Milan fans, but also by Juventus fans, indeed considering what have Bonucci done (emotional celebration in front Juventus crowd) in both clubs the last match.

There were several direct Milan and Juve transfer. We knew Marco Storari, Nicola Legrottaglie or Alessandro Matri. But these transfer had no significant effect on the opposite. The newest direct transfers from Juve to Milan involving high profile names are Mattia Caldara and Gonzalo Higuain.

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I would rate the sweetest taste from Milan and Juventus direct transfer it was Filippo Inzaghi deal for Milan side. Why? Because he came as “bottle” and slight injury-prone, but later change into legend with massive contribution after joined Milan from Juventus.

The second one; the latest transfer or Caldara-Higuain. Promising defender and proven attacante. With Caldara and Romagnoli in the backline, Milan is already building the great-wall for future with them. While Higuain, as the instant solution for our lack of sharpness previous season and also beneficial for Patrick Cutrone, to learning to experience from a lethal striker in Serie A such Pipita.

In other hands, more than Leonardo Bonucci “betrayal action”, the most bitter one from direct transfer results between Milan and Juventus it was Andrea Pirlo’s move. It was the old management ignorance by underestimating his capabilities. Honestly, Pirlo to Juventus it was like providing free aid to Juventus in their revival action and become fortress until current constellation.

To be honest, mostly Milan fans didn’t regret on Bonucci departure after the arrival of Caldara and Higuain. We should really be enjoying this summer after the doubtful owner Yong-Hong Li and Co disappearing and the real positive change happening under Elliot group as the new owner. Anyway, well-restructuring on management (Leonardo and co) and seriousness on mercato are what Milan fans demand since a long time, isn’t it?