South American star Gustavo Caballero spotted in Portsmouth as Blues close in on fifth January addition

It’s poised to be a thrilling end to proceedings in the winter transfer window for Pompey.

John Mousinho’s men are expected to be active in the final knockings, with incomings and outgoings on the cards before Monday’s 7pm deadline.

Among those who are set to arrive at PO4 is Gustavo Caballero, with The News understanding the 24-year-old is closing in on a switch.

The versatile winger is set to become the fifth new arrival of the window and will pen a loan deal for the remainder of the campaign.

According to reports in Paraguay, that deal would also involve an option to buy in the summer.

Speculation over a move has ramped up furthermore, with a photo of Caballero in Portsmouth emerging on social media.

An image posted by Sants2304 on X, shows the Santos talent sat in the Village Hotel alongside representatives as he closes in on a switch to the Championship.

The winger, who can operate either out wide or in attack, will bolster Mousinho’s frontline amid continued uncertainty over Callum Lang’s future.

The Blues are also still without Josh Murphy, Harvey Blair, Franco Umeh, Florian Bianchini and Thomas Waddingham, who are sidelined due to injury.

Meanwhile, Millenic Alli and Keshi Anderson have both arrived earlier in the month to bolster the forward department.

Who is Gustavo Caballero?

After coming through the ranks with Paraguayan outfit Deportivo Capiata, Caballero made the move to Ameliano before sealing a switch to Club Nacional in 2022.

During a three-year stay with the Primera Division outfit, the forward netted 20 goals and provided seven assists in 107 outings in all competitions.

The Paraguay youth international then completed a $1.6m move to Brazilian top-flight outfit Santos in 2025, where he’s registered two goal contributions in 14 outings.

Caballero is now on the English south coast finalising a move to Fratton Park, where he will link up with Mousinho’s Championship outfit.

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John Mousinho on Pompey’s end to the transfer window

Pompey have Alli, Anderson, Makenzie Kirk, Conor Chaplin and Adrian Segecic as the sole options out wide and in attack after Colby Bishop rolled his ankle against West Brom on Saturday.

When asked how many signings he wants to make before Monday’s deadline, the head coach admitted a late judgement call will have to be made over any more arrivals depending on the Magic Man’s injury situation.

He told The News: Maybe a couple more (than two). We’ll see how Colby’s ankle settles down, that’s an important factor.

‘It might be one of those where we’ve got to make a judgement call on it because we may not get the full extent of the injury by Monday evening. We’ll have to see on that.

‘It’s a real shame because I thought Colby was brilliant today (against West Brom). Dominated.

‘I thought it was his best performance of the season which is a real shame.’

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