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Ranking Milan’s Leftbacks Post-Maldini

Ricardo Rodriguez is set to break the trend of terrible leftbacks in the Post-Maldini era.

AC Milan v Calcio Catania - Serie A Photo by Marco Luzzani/Getty Images

The leftback position has been a problem spot for the Rossoneri since Paolo Maldini retired in 2009. With the signing of Ricardo Rodriguez, it finally looks as though Milan have truly filled the void. As a cathartic exercise we ranked every leftback Milan have had since Maldini retired. Let’s take a walk down memory lane and have a chuckle at those who tried and failed to fill the leftback position.

9. Didac Vila

Signed from Espanyol in 2011, there was great hope that Vila, then a regular for the Spanish youth sides, would develop into a starter on the left side of the Rossoneri’s defence. Safe to say that did not work out as Vila went on to make exactly 1 appearance for the Rossoneri in the 4 years he was owned by the club. He finally departed to Greece in 2015 after being loaned out to La Liga three years in a row.

8. Taye Taiwo

The fact that Taiwo isn’t dead last on this list is laughable as he’s one of the biggest flops in recent Milan history. Signed on a free transfer from Marseille in 2011, there was great hope for Taiwo as he had amassed almost 200 appearances for Marseille and joined Milan at the ripe age of 26. He lived up to precisely none of they hype however, and suited up just 6 times in Rossoneri. Taiwo has a a real case for last place on this list, but his virtual self was pretty useful in FIFA due to his pace and shot power which is just enough to give him the edge over Didac Vila.

7. Kevin Constant

One of the most horrendous players to ever sport a Milan kit, Kevin Constant somehow managed to rack up just under 60 appearances for the Rossoneri in three seasons. Constant was signed as a midfielder, but was the subject of one of Max Allegri’s brilliant experiments and was converted to a leftback where he was nothing short of shambolic. A defensive liability, clumsy in possession, and tactically clueless, the name Kevin Constant should send a shiver down the spine of Milanisti everywhere. Somewhat amazingly, Constant isn’t dead last on this list, which says more about the complete and total failure of both Taiwo and Didac Vila then it does about Constant’s (very very limited) ability.

6. Djamel Mesbah

In January of 2012 while still in the Champions League, Milan decided to finally address their leftback problem. So what did they do? They evaluated all options and decided the guy that they needed to take their squad to the next level was Lecce’s leftback. This move made no sense then, and makes no sense in retrospect. Mesbah was expectedly terrible, but perhaps the worst part about him was that he was flipped to Parma for Cristian Zaccardo one year later.

5. Urby Emanuelson

Emanuelson arrived as a promising prospect hailing from Ajax’s distinguished academy, but its safe to say that his career has followed a strange path. Emanuelson was a subpar and defensively useless leftback for the Rossoneri before being converted to a left winger and then a trequartista under mad scientist/manager Max Allegri. Shockingly, the conversion didn’t workout and Emanuelson departed the Rossoneri in 2014. He currently plies his trade in the Championship with Sheffield Wednesday in case you were wondering.

4. Leonel Vangioni

This past season was Vangioni’s first with the Rossoneri, and in just over a dozen appearances for Milan the Argentine has looked thoroughly average. On this list, thoroughly average puts you in the top 50th percentile.

3. Luca Antonini

Luca Antonini was a good soldier for Milan. He was never “Milan quality” but was a hardworking yet error prone player who somehow transformed into Paolo Maldini whenever Milan played Barcelona in the Champions League. All in all Antonini wasn’t THAT bad.

2. Luca Antonelli

A product of Milan’s academy, Antonelli left the Rossoneri in 2008 having made just 1 appearance for the club. After establishing himself at Genoa and earning the captain’s armband, Antonelli returned to Milan in 2015 and has been a stabilizing presence ever since. The veteran is far from the most talented player on the pitch, but never turns in less than a full effort. Antonelli could be a useful depth player for the Rossoneri going forward and it would be nice to see his loyalty rewarded with a bench role in the “new Milan”.

1. Mattia De Sciglio

Coming in at number 1 on this list is current (at least for the next couple weeks until he’s sold to Juve) Milan leftback Mattia De Sciglio. De Sciglio burst onto the scene as a graduate of Milan’s academy in the 2012-2013 term and quickly garnered attention for his outstanding performances. He was dubbed the “New Maldini” due to his emergence from the Primavera and the fact that he was a right-footed leftback. Since his debut season De Sciglio’s play has declined significantly and he now looks like a shell of the player he once was. When he is sold this summer the majority of the fanbase will be happy to be done with him, while those who are disappointed are holding on to a 30 match sample size of a 100 match career. Luckily for De Sciglio, his early performances carry him to first place on this ranking list, as he comes out on top of a sorry bunch.

Take a deep breath Milanisti, Ricardo Rodriguez is here. It looks like the nightmare is about to end. Finally.