GdS: Kessie, Paqueta, De Ketelaere and Brahim among ‘the regrets of the Diavolo’

By Oliver Fisher -

It is not uncommon in football that players can struggle at some clubs and perform very well at their next team, but for AC Milan there is a list of cases that make for interesting reading.

This morning’s edition of La Gazzetta dello Sport (seen below) has a page titled ‘The regrets of the Diavolo’, focusing above all on the exploits of two attacking midfielders who were at the club last season but left.

It starts with a look at Brahim Diaz, whose goal was enough for Real Madrid to beat RB Leipzig in the first leg of their Champions League round of 16 tie. As a reminder, in the last edition of the Champions League last 16, his goal won the tie against Spurs.

Two nights ago, Brahim said: “I feel great in Madrid, but I was also fine at Milan. I experienced a fundamental moment there and I thank everyone for three magnificent years. I follow them and will always follow them, I talk more with Theo Hernandez than with my girlfriend.”

On the other hand, Charles De Ketelaere and Milan never seemed to get their hearts to connect after a season with 40 games but zero goals. He was warmly welcomed at the beginning, before going very cold in the second half of the season.

Instead, the Belgian seems love struck with Gian Piero Gasperini at Atalanta: 10 goals in his first season so far, the most recent against Genoa with an incredible left-footed strike from distance.

Away from the pressure of San Siro and closer to the opponent’s area, CDK has reconnected with his seasons as a top scorer at Club Brugge and that will no doubt leave the Rossoneri reflecting on why a €35m investment did not work.

The story with Franck Kessie and Hakan Calhanolgu ended even worse. The first went to Barcelona, ​​the latter to Inter, without Milan receiving a transfer fee for two players who certainly had a value.

Kessie had been the Rossoneri’s protagonist in the year of the Scudetto and recently helped the Ivory Coast to victory in the African Cup of Nations. In Spain he won LaLiga and the Super Cup, meaning he got used to success. As well as the stellar salaries guaranteed in Arabia by Al-Ahli.

The salary was the basis of the break with Milan: in the summer of 2022, to extend the expiring agreement, he asked for a fee of €7m net per season which was equal to what Zlatan Ibrahimovic then received.

The management’s offer wasn’t much lower: €5.5m plus bonuses. Barça offered a bit more and it was enough for the Ivorian to say yes, thus ending his experience at Milan after half a decade.

Inter arrived in the summer of 2021 to bridge the gap between Calhanoglu’s request for a salary (€5m) and Milan’s offer (€3.5m) but then a year later the Rossoneri became champions without him.

Now, Inter being the leading candidates for the title with Calhanoglu as a driving force. Betraying one half of the city to accept the richer offer of the other was the cause of tension, controversy, teasing and banners.

What about a midfield three with Kessie, Calhanoglu and Lucas Paquetà? The latter was purchased by ex-director Leonardo for €38m and he saw some kind of Kakà-like ability in him, but it turned out to be an unfulfilled promise.

The result is that the Brazilian was sold to Lyon after a year and a half for just over half the purchase price, but today Paquetà is in the Premier League with West Ham with whom he won the most recent UEFA Conference League.

He played at the 2022 World Cup as a starter for his country and in the summer Manchester City would have paid €100m for him, but the midfielder was being investigated by theEnglish Federation for betting and gambling.

Paquetà has always denied the accusations and continues to be decisive in the Premier League (but still with West Ham), while Milan did not change and instead they have actually stuck to their guns.

There was a spending limit on wages that they did not want to exceed, even at the cost of losing the players for nothing.

Tags AC Milan Brahim Diaz Charles De Ketelaere Franck Kessie Hakan Calhanoglu Lucas Paqueta


  1. The only regret should be not having moved faster for Thuram. We offered 4 million to origi but didn’t want to offer 6 million to thuram. Great management!

    1. But but many experts here said that we dodged a bullet by not signing Thuram?

      And now they sealed Taremi too after we chased him all summer long. Just when we can get him for free, we’re (or the management to be precise) no where to be found.

  2. Meanwhile Inter sealed an extention with Barella increasing his wage from 6 to 7 millions. We, in the meantime, lowball and then rather sell then try and hold on to our core.

    So here’s the anwser to why Inter are doing better than us. If RedBtid continue to sell our prized assets and core players, thinking they can replace them with algorithmically similar but cheaper alternatives they and fans here are deluded.

    1. Ted their are many “fans” here that are more interested in the accounts than the football.

      Inter despite their financial problems have put together a brilliant team, with a legitimate chance of winning CL

      1. We call those who aren’t concerned about the finances of the club morons. The fate of Everton, Leeds, Parma and Fiorentina is a warning of what can happen when irresponsible spending catches up. Management have spent heavily in the summer and put down €40 million to buy land for a new stadium so what are you complaining for?

      2. We call those who aren’t concerned about the finances of the club buffoons. The fate of Everton, Leeds, Parma and Fiorentina is a warning of what can happen when irresponsible spending catches up. Management have spent heavily in the summer and put down €40 million to buy land for a new stadium so what are you complaining for?

        1. No one said to spend irresponsibly, why are you putting words in our mouth? They sold a core player to get bunch of average ones and from foreign league as well. Right now the only player paying off is Pulisic, the rest are bench numbers at best. I could say that was a bit irresponsible.

    2. Yeah then why didn’t your precious Maldini seal the deals with Kessie Hakan Dollarumma and Romagnoli because letting them go for free?

      nothing is his fault right? only Redbird’s fault even though THEY WERENT EVEN THE OWNERS BACK THEN.

      1. Who’s talking about Maldini, Hakan, Kessie, Donna? You’re either lost or drunk. But since you started, yes he wanted to renew and try all the way to the end but Elliott and Gazidis imposed salary cap. Also, Kessie said “don’t worry we’re going to renew”. Doesn’t sound like Maldini’s fault when one’s a moneygrabbing, backstabbing ho?

        1. So sell him, stop being so gullible

          ‘oh he pinky promised me he’s gonna sign so i will let him go into his final year’

          “oh Renato Sanches pinky promised me he’ll sign and i love him for whatever reason so i ignored ENZO WHO WANTED TO COME HERE”

          You work within your means, you dont work magically hoping Milan can spend money we dont have

          1. You can literally google it, Enzo’s agent said it

            but you are Ted, dumb af and you think you are smart so you wont google it because you arent smart enough to look anything up

            how are you even alive like this?

      2. We don’t sell Gigio, but he helped us reached UCL after 8 years. We don’t sell Kessie, but he helped us win Scudetto. Sometimes it’s something beyond on paper money.

      1. Yeah it would be too much to sell two in their first year at helm. Let’s see what player they’ll sell in year two, there are many candidates – Maignan, Tomori, Theo…

        1. better than your favourite Maldini letting everoyne go for free and then complaining he has no money when he freaking lost the money himself

          imagine if he actually signed Renato Sanches at 5.5m/yr we’d be stuck with that dead weight

    3. I suppose it’s better to let them leave for free the way Maldini did?
      They sold Tonali and it was a brilliant decision to do so seeing as Newcastle way overpaid for him and it allowed us to strengthen our team in many positions. Not to mention that Tonali is suspended for a year and if we didn’t sell him and bring in reinforcements we would probably be bottom of the table right now.

      1. The scandal and his suspension really came after they sold him so it’s quite unfair and hypocritical from fans throwing that in front as somekind of excuse. And he’s miles better than any of these bench extentions they bought with his money

      2. 2023- Tonali, Bennacer, Adli, Krunic

        2024- Bennacer, RLC, Musah, Adli, Reijnders

        Lets be real, if we had a choice tonight from the above it would be Adli+Tonali in the center with Bennacer as AM

        If we still had Kessie he would start too

        Our midfield is disimproving year by year because we are not keeping hold of our best players.

        (forget about Tonali’s ban, that had nothing to do with his sale, plus he will return. It’s not relevant)

        1. I’m taking 2024 Midfield every day of the week. And the results have shown that to be true. The problem is people just can’t accept that Tonali was and is nowhere near as good as the hype. That sale was an absolute steal.

  3. More GDS BS. Diaz and Paqueta are not regrets.
    Diaz has 4 goals and 1 assist this season. People need to stop pretending he’s tearing up La Liga or the UCL, he isn’t.

    Paqueta has 2 goals and 5 assists.
    Pulisic has 6 goals and 5 assists.

    There are no regrets for any of the players that have left. They didn’t want to be at the club, most of them didn’t perform.

    1. most sensible comment on this thread…Add to your point, they arent regrets because they simply didnt work out with us. it happens all the time for whatever reason. Paqueta was perhaps too new to Europe, CDK too young.. etc. Some guys suck on one club and go big on another, some guys are the opposite. Go look at any club and you’ll see a ton of these cases

    2. According to people here, Milan sucks, worst club in Italy

      I can guarentee you some of them here celebrate when Milan loses because then they can go to twitter and reddit and push their anti-Pioli/Redbird agenda, god forbid Milan does well that would make their past summer outburst look dumb af

  4. The biggest regret here is that Milan bought CDK in the first place. If the money were spent on Botman maybe Milan wouldn’t have lost to Inter in the semis and perhaps could have challenged Napoli for the scudetto.

    Ifs and buts are so useless. Focus on now and not “what could have beens”

    1. Milan’s failure against Inter wasn’t down to missing one quality CB. It was a tactical/system error by Pioli, trying to press high and man mark opposition with defenders who aren’t suited for it.

      1. Botman could have effected Milan’s tactics all together. And defense was leaky as f*** in January. Who knows, with the right players/defenders…

  5. CDK is not a regret, it’s a mistake we signed him before firing Pioli, he was never going to succeed under Pioli, he Simply does not fit the formation

      1. Your response makes ZERO sense, yet you’re bashing him??? LMAO!!! Classy Cat.

        CDK did not fit into Pioli’s ONE striker system. CDK didn’t cut it as an AM, nor a winger, nor a striker.

        Gasp plays TWO attackers and gives CDK the freedom to move around. (irrelevant what Motta or DeZ do)

        kid spent a year milan afraid of his own shadow. It’s not due to lack of time.

        Lastly, don’t call people dumb if you don’t even understand their comment. Makes you look like a douche canoe.

  6. – Paqueta was sacrificed to get Leao. No regrets there. Sure its nice to live in a fantasy world where we can afford everyone, but in the real; world you need to make choices an we made the right one.
    – Diaz wanted to return to the mothership, and RM wanted him back. And very few people were happy to cough up 20M for him in the summer, which frankly woudn’t even be close enough to pry him away.
    – CDK was drowning here. He needed a life line, and we managed to avoid bigger losses on him. Sure maybe we could have found better loan deal, but it’s easier said than done. Most likely he wouldn’t have wanted to go play for a small club, and bigger clubs would not have him on dry loan. I refuse to believe that Milan opted to not go for a dry loan if that was a realistic option.
    – We should have payed Kessie. He’s made the least impact away from Milan, but he is the piece that our squad is missing the most.

  7. This article must be for all the Maldini and Pioli fan boys, especially the fanboys who think that Maldini is so superior to all directors in Serie A.

    The majority of these players from Paqueta, Calhanglu, Kessie, Brahim Diaz and CDK were the fault of Maldini and Pioli. They are the ones who made all the mistakes that caused all these players to leave.

    Paqueta was used by Pioli as an attacking midfielder when he should have been deployed as DM. So of course it didn’t work out. In a 4231 system Paqueta should’ve played alongside Kessie. Pioli is to be blamed for that.

    Brahim Diaz was signed on a 2yr dry loan with NO obligation or option to buy. So it’s no surprise that Real Madrid wanted him back when he improved with us. That was a bad loan deal to start with. Who is to be blamed for that? Definitely not Redbird because they weren’t the owners of the club. Another L for Maldini.

    Calhanoglu and Kessie wanted more money to stay but some how our genius director Maldini waited until both their contracts ran out instead of selling them if Elliott wasn’t going to pay them what they wanted. Another L for Maldini since Redbird wasn’t the owners of Milan. Sigh

    CDK was signed for 35m. Why didn’t Maldini use that money to sign Botman? That would have made more sense instead of signing CDK who in my opinion Pioli didn’t want but was forced to take. Dybala was a free agent and even if he is injury prone he would’ve offered more than CDK because of his experience and quality. Another L for Maldini.

    Bottomline is that Milan is better off without Maldini and Pioli. Our scudetto was out of pure luck and more importantly Ibrahimovic influence on the team. The only good thing Maldini did was to resign Ibra. End of story.

    1. Hindsight is always 20/20, man. Easy to sit here and judge but you don’t really know how everything played out and what the deciding factors were. None of us do, yet everyone comes in here preaching the rights and wrongs like Gospel.

      Your post sounds more of a Maldini bash than an objective input.

  8. So Ollie, are you saying if Milan didn’t let any of those players leave the club would have a second star and 10 CLs? Given where Milan were in 2019 I have no regrets

  9. Diaz and real had a buy back option in the loan deal, there was nothing we could do to keep him. Kessie wanted to leave just like Donna, we did everything we could to keep them. You can’t regret something that is out of your hands. However Paqueta would have been a nice addition to the squad, but I don’t think it’s that much of a regret as we replaced him well with players like Bennacer and Tonali where we doubled our money

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