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Why Riccardo Montolivo’s premature retirement is a lesson in trading immortality for mediocrity

Riccardo Montolivo hasn’t played a Serie A match for 18 months.

For some, hearing that a 34-year-old midfielder struggled to get game time in the final few years of his AC Milan career — with plenty of competition for places — isn’t perhaps too surprising.

But for the former Italy international, who announced his retirement from football on Wednesday after being released from his contract by Milan at the end of last season, it’s the principle of how his career ended that’s left a bad taste.


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Montolivo failed to make a single appearance for Milan during last season’s Serie A campaign

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Montolivo failed to make a single appearance for Milan during last season’s Serie A campaign

“I will continue to live in Milan with my family,” he told Corriere dello Sport upon his announcement.

“What I’ll do now, I don’t know. I have to think about it.

“You could say [Milan] forced me to stop playing. I didn’t even get the chance to say goodbye to the fans after seven years.”

But few Milan fans will care too much about his departure or subsequent retirement; nor will the fans of his former club Fiorentina, for that matter. 

Having been released in the summer, Montolivo has decided to retire

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Having been released in the summer, Montolivo has decided to retire

The midfielder spent seven seasons at Fiorentina and even captained the side, before joining Milan on a free transfer in 2012.

And the general feeling in Florence following his retirement is that of ‘what goes around, comes around’, with fans believing he traded immortality for mediocrity when he moved to their rivals.

In an open letter to supporters after leaving the club to much controversy, he wrote: “In life and in professions, relationships can break down and not always in an understandable and painless way for everyone.

“Although some see me as an enemy, I can only wish joy and satisfaction to Fiorentina, Florence, to my former comrades and all the people who work every day in the club with passion and dedication.”

An apology, of sorts, but not one fans were willing to accept.

The midfielder was loved at Fiorentina until his move to Milan

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The midfielder was loved at Fiorentina until his move to Milan

At Milan, he had the world at his feet.

Following his role in Italy’s route to the final of Euro 2012, his arrival to the San Siro was met with much optimism.

Of course, he was booed mercilessly by the Florentines upon his first visit back to the Artemio Franchi Stadium in 2013, but silenced them temporarily with a great goal and an assist in a swashbuckling 2-2 draw.

But the beginning of his Rossoneri spell coincided with the club’s firm fall from grace, which has included a lack of Champions League football in the last six seasons and no league title since the 2010/11 campaign.

In fact, Montolivio’s only honour in the colours of Milan is the Supercoppa Italiana in 2016, which is Italy’s equivalent of the Community Shield.

What’s worse is that his time at the club — especially the last four years — have been blighted by a lack of form, problems with injuries, and controversy.

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When club legend Clarence Seedorf was appointed as manager mid-way through the 2013/14 season – with Milan just four points above the relegation places at the time — he begun by benching some of the senior players who weren’t performing.

Montolivo was one of them and reportedly led to the captain leading a mutiny against the Dutchman, ultimately leading to his sacking just four months into his tenure.

“With Seedorf, there wasn’t much harmony, the decision to sack him was for the good of Milan,” Montolivo told the media afterwards.

If going against Seedorf wasn’t enough to irk the fans, then his string of mediocre performances certainly were taking their toll.

But much to the fans’ dismay, he signed a contract extension in 2015 just a month before his 31st birthday — the same age that Andrea Pirlo was when he was told he couldn’t have a renewal.

Montolivos career was blighted by injuries

Getty Images - Getty
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Montolivos career was blighted by injuries

The same player / manager strong-arming occurred with Gennaro Gattuso, another Milan hero, who coached the team between 2017 and 2019.

It appears Gattuso was harder on the midfielder than previous regimes, and the two seemingly fell out behind the scenes.

“I was marginalised, answers were never given. But I don’t hold a grudge,” Montolivo said in his recent statement, hinting at Gattuso’s term.

“Those who have been wrong with me, those who have disrespected me, repeatedly, will probably come to terms with their conscience.”

Montolivo’s Milan career spanned seven years, but he only picked up a single winner’s medal

EPA
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Montolivo’s Milan career spanned seven years, but he only picked up a single winner’s medal

Montolivo also lost the Milan captaincy to Leonardo Bonucci upon the defender’s arrival from Juventus in 2017, a decision that came with very little prior warning.

“I didn’t deliver [the armband] to him,” he said.

“They told me that [then owner] Li Yonghong had decided the armband would be passed to one of the new signings.

“When they told me about it, I explained that I found it unfair, that they were making a big mistake because there are hierarchies in the locker room that should always be respected.”

He then didn’t make a single appearance for Milan last season, despite being named on the bench 17 times in the Serie A.

He ultimately described his final year-and-a-half at the club as ‘an ordeal’.

Bonucci took the captain’s armband when he arrived in 2017

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Bonucci took the captain’s armband when he arrived in 2017

As a free agent, Montolivo clearly struggled to find a new club and his decision to retire prematurely will be met with a shrug by much of his former club’s fan base.

He finishes his career with a reputation as one of Italy’s most stylish deep-lying playmakers in recent times, a nearly-man whose injuries overshadowed his promising early-years, and a captain who lacked leadership qualities that polarised fans.

There’s certainly a lesson to be learned here, although it may take time for Montolivo to realise. 

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