With the mid-season transfer window in full swing, Inter Milan fans are hoping for at least a couple of great transfers to help propel the Nerazzurri to a twentieth Serie A title.

For the Inter Milan fans who like gambling, however, the odds of Inter winning the Serie A with what they have may seem much greater than the club actually making new impactful signings this January.

It’s almost a cliché at this point, but Inter just hasn’t had much luck with deals on the transfer market during and after the Moratti era. Of all the great ways for someone to make a good deal – from massive discounts on Black Friday to online casinos that credit a bonus to new clients on sign-up – Inter Milan shopping around for new players rarely results in a good outcome.

Hopefully, this year will be different. So let’s take a stroll down memory lane and explore some of the most disappointing Inter Milan transfers of the last three decades. 

Vratislav Gresko

Gresko is one name that makes most Inter fans’ blood boil. The Slovak defender came to Inter for €4.8 million from Bayer Leverkusen in 2000. He then went on to unintentionally cause one of the most famous collapses in Inter’s history.

During a game against Lazio at the end of the season, Gresko famously headed the ball backward to Lazio’s Karel Poborsky, who scored.

After that, the end result read 4-2 for Lazio, which effectively gifted the Serie A title to Juventus even though Inter was ready to win it for the first time in 13 years. Gresko was then sold to Parma a month later, and everyone from the blue half of Milano has been trying to forget about him ever since. 

Gabigol 

Brazilian strikers such as Ronaldo or (early) Adriano have brought great joy to the Interisti over the years. Meanwhile, the Santos goal-scoring machine, Gabriel Barbosa Almeida, commonly known as Gabigol, cost Inter €30m in 2016, even though he was just 20 years old at the time.

Despite the high expectations, Gabigol simply didn’t handle the switch to Serie A too well. He initially scored only one Inter goal before embarking on a loan spell to Benfica and then back to Santos.

He eventually rekindled his goal-scoring form when he moved to Flamengo, but for Inter, he’ll be remembered as a disappointing transfer. 

Kerlon

The Kerlon “The Seal” case is so bizarre it almost feels like it belongs on a different list. The good news was that he only cost the Nerazzurri €1.3 million when he arrived from Cruzeiro in 2008.

The bad news was that Inter seemingly bought him for the one trick he’s famous for – balancing the ball on his forehead while running forward, baiting opponents to foul him.

While admittedly entertaining the first time you see it, this trick doesn’t make for a complete footballer.

Thus, Kerlon Moura Souza never really managed to achieve consistent playtime at Inter. He was continuously loaned to other teams, but no one wanted to buy him, and he eventually retired at 29. 

Fabian Carini

Leave it to Inter to get a player who would fail to impress and get him in a swap deal with a future World Cup and Ballon d’Or winner, Fabio Cannavaro.

We’ll probably never know exactly why Inter failed so badly with this deal – not only did they let Cannavaro leave for one of their biggest rivals in Serie A, but they got saddled with a player who was underwhelming during his time in Turin and continued to be just as unimpressive in Milano. 

Ricardo Quaresma

Quaresma is another player whose transfer brought a lot of hope to the Interisti. In his case, however, the hope was more for the new manager, Jose Mourinho.

Quaresma was one of the summer transfers that the club signed at at Mourinho’s request, as the Portuguese wanted to revamp the team and needed wingers to do so.

Sadly, even though Inter had to pay €19 million to FC Porto for Quaresma, the off-the-cuff player never found his place in Serie A and was first loaned to Chelsea and then sold to Besiktas. 

Cyril Domoraud

Cyril Domoraud is something of a legend at Inter, albeit not in a good way. The Ivorian only ever played six games for Inter after transferring from Marseille for €7 million in 1999 and before being returning to France.

However, what makes his stay at the San Siro memorable is that Juventus director Luciano Moggi reportedly tricked the Nerazzurri into buying him by intentionally overpraising the player aloud in front of an Inter scout. 

Andy van der Meyde

Van der Meyde cost Inter “only” €6 million when he arrived from Ajax in 2006. That’s a notably lower sum than most of the other transfers on this list, but the Dutchman was one of the most promising signings Inter had done at the time.

However, a familiar pattern repeated – van der Meyde had two underwhelming seasons at San Siro and then moved away. Even after transferring to Everton, he couldn’t restart his career and eventually retired at 32. 

As frustrating as the seven transfers above were, we’re obviously exaggerating a bit when we say that Inter making a successful transfer is next to impossible.

In fact, the Nerazzurri have signed quite a few great players during and after Moratti’s reign, which has led to six Serie A titles, a UEFA Champions League and UEFA Europa League wins, a Club World Club win, six Coppa Italia, and more.

With or without major new signings in January 2024, the current Inter squad is strong enough for more silverware too, as attested by none other than their chief rivals in the league.