5 Worst Signings In AC Milan History

AC Milan has had no shortage of success over the club’s history that started at the tail end of the 19th century. Since then, AC Milan has won a long list of titles in Serie A, UEFA, and FIFA. The club is also one of the richest, meaning that it can afford just about any player imaginable. Not all of those big-money signings end up working, however.

There have been many instances of AC Milan shelling out millions to players, only to have it blow up in their faces. Here are the five worst signings in AC Milan’s history. Before we start the list, some of the other players who just missed the cut (fortunately for them) include Ricardo Oliveira, Luther Blissett, and Jose Mari.

Leonardo Bonucci

Center-back Leonardo Bonucci has had a pretty interesting career. After starting as a professional with six different clubs within four years, Bonucci finally found a home with Juventus in 2010. During his seven years there, Bonucci played in 227 league matches and netted 13 goals while winning the Serie A title several times. In July 2017, Bonucci signed a five-year deal with AC Milan worth €42 million.

Things got off to a good start when Bonucci became team captain, but his performance in the first season was less than stellar. Bonucci, despite the long-term deal, played in just 35 total league matches and scored two goals. AC Milan didn’t win any major titles in his one year, and he was shipped back to Juventus in exchange for Mattia Caldara, which leads us to our next player.

Mattia Caldara

Playing the same position as Leonardo Bonucci, Mattia Caldara got his career started with Atalanta in 2014 after more than a decade with the youth program. The Bergamo native also spent time with Trapani and Cesena on loan before joining Juventus. While with Juventus, Caldara would be loaned out again, spending almost all of his time with his original club. In 2018, Caldara was part of the Bonucci swap and was given a five-year, €35 million deal.

Injuries took their toll immediately as Caldara didn’t appear in a single league match for AC Milan. He appeared in the Europa League and Coppa Italia for the club but was almost immediately sidelined due to a ruptured ACL. With that, AC Milan used Caldara as a loaner for multiple clubs instead. He made yet another return to Atalanta while also playing for Venezia and Spezia.


Digao was supposed to be the next big thing to come out of Brazil and there were a lot of clubs interested in his service around the world. His youth career started with Sao Paulo, and he came to Italy as part of Sampdoria until being loaned to AC Milan. The club then signed him to a lucrative deal and he made his senior squad debut in 2005. Over the next six years, though, Digao appeared in just one Serie A game.

Digao was loaned out to Rimini, Standard Liege, Lecce, Crotone, and Penafiel throughout that time. Unfortunately, he just was never able to break into the lineup for AC Milan and he joined the New York Red Bulls in the United States for a brief period at the end of his career. Now, Digao is the ultimate ‘what could have been’ story for AC Milan.

Oguchi Onyewu

Speaking of players who spent time in the United States, Oguchi Onyewu was actually born in the country, calling Washington D.C. his home. Onyewu moved down to Florida where he enrolled at the IMG Academy before heading to Clemson University. Onyewu headed to Europe where he played for Metz, La Louviere, Standard Liege, and Newcastle United from 2002 to 2009.

AC Milan then signed Onyewu to a three-year contract but had some injury issues that limited him to just a single Champions League match. He never appeared in a Serie A game and was loaned out to Twente for a brief time during his two years with AC Milan. When he left the club in 2011, Onyewu played just 60 league games for the rest of his career which lasted for six more years.

Fernando Redondo

There are a lot of interesting details in the Fernando Redondo story. The midfielder had a brilliant career heading into the 21st century after having spent his career with Argentinos Juniors, Tenerife, and Real Madrid. AC Milan acquired Redondo for £11 million, with Redondo having no say in the issue.

Almost immediately, Redondo suffered a serious injury that kept him out of action for more than two years. Luckily for AC Milan, Redondo said he wouldn’t take a salary while not playing and even wanted to give back the house the club paid for, as well as the car. Redondo made just a handful of appearances toward the end of his career, thankfully able to contribute before retiring.

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