Liverpool 'gamble' fails, January exit now likely for 83-goal star

Over the years, Liverpool have taken many different gambles on players and managers.

For example, it was a gamble for Fenway Sports Group to hire Arne Slot after Jurgen Klopp resigned and, it was also a gamble for them to replace Andy Robertson with Milos Kerkez.

Sometimes, these gambles pay off but, more often than not, they leave at least one party unhappy.

This season, the Reds needed to replace Mohamed Salah and, even though everyone thought that they'd be bringing in a natural right-winger to replace him, they've gambled and seem to have chosen to do at least the first half of the 2025-26 season with four left-wingers among their ranks.

At the moment, this seems to be paying off as the Anfield outfit are unbeaten in the Premier League but, there are other moves that they've made which have failed to live up to the same standards.

And now, the Reds and the player could end up paying the price for this mistake.

Federico Chiesa's gamble of staying at Liverpool has failed miserably

Federico Chiesa is one of the many Liverpool players who the club have tried to move on since they signed him.

When he was brought in for £10 million a few years ago, everyone thought he was going to be the bargain of the century but, since his return from his ACL injury, he's just not been the same player.

His time at Anfield has been littered with injuries and, even though he was fully fit for most of the 2025-26 season, Arne Slot still chose against playing him.

Fans thought that the Italian would have another chance to prove his worth to Iraola but, even the Spaniard has side-lined him.

Indeed, he is nursing another injury at the moment but, the fact that Liverpool tried to sign Yankuba Minteh and Ismaila Sarr until the dying embers of the transfer window proves that Chiesa isn't in Iraola's plans.

This has obviously led to questions being asked about his future and now, thanks to an update from Tutto Juve, the attackers stance on his future seems to have been shared, especially after his omission from Liverpool's Champions League squad.

"The failure to be called up for the Champions League could be a decisive signal for the upcoming transfer window. Chiesa will have English competitions at his disposal to try to change the hierarchy, but his playing time in the Premier League also risks being limited," they wrote.

"Liverpool have numerous attacking options, and Iraola appears to have identified other players for his project. Without a turnaround, a winter transfer window could become a possibility.

"The decision to stay at Anfield thus turned into a very complicated gamble. Chiesa wanted to relaunch his career with Liverpool; their exclusion from the Champions League, however, already forces him to pursue other options."

Federico Chiesa needs to leave Liverpool in January

Although most of Liverpool's fanbase wants Chiesa to succeed at Anfield, it's clear that isn't going to happen.

The attacker has now been with the club for a couple of years and, even though his managers haven't really trusted him, he's also failed to impress Iraola.

Not only does this prove that the Italian is just not the player that he used to be but it also shows why he needs to leave Liverpool as soon as possible.

The attacker was initially brought in to be Salah's understudy and, while he managed to do this a couple of times, he often fell below expectations.

So, despite his experience and the fact that he's arguably Liverpool's only right-winger, it feels like now would be the best time for both parties to cut ties with one another.

If not, Chiesa will stagnate even more and end up exiting L4 for nothing in the future which is far from ideal for Liverpool.