Liverpool are often liable to do things no one quite expected in the transfer market.

The Reds are one of the most meticulous clubs in the world when it comes to buying players and are not afraid to go against the grain when doing so.

This approach has often led to criticism from Liverpool fans.

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While some would argue De Bruyne is past his best and would be far too much of an expensive gamble for Liverpool, recent football history throws up some very good examples which suggest that may not be the case.

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While the eyes of the football world were glued to events in Paris for the Champions League semi-final between PSG and Arsenal on Wednesday evening, journalist Gianluca Di Marzio broke some major transfer news.

According to the Italian reporter, De Bruyne has an offer to join Liverpool, while Napoli are also said to be involved in the battle to sign the 33-year-old.

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This has come on the back of excitement from Liverpool fans that De Bruyne could join, but the Belgian swapping the Etihad Stadium for Anfield never felt like a genuine possibility.

Until now.

The last player to go directly from Man City to Liverpool also did so on a free transfer.

In 2015, James Milner rejected the chance to stay at City and instead joined the Reds aged 29.

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Although a veteran at the time of his signing, Milner stayed at Liverpool for eight seasons, winning just about everything with the Reds.

Given his age and where he’d be coming from, some are already drawing comparisons between De Bruyne and Milner.

Having been deemed surplus to requirements after 10 years at AC Milan, Pirlo joined Juve at 32, becoming a key player over four years and winning a quartet of consecutive titles.

Although De Bruyne will be two years older than Pirlo was when he made his move from Milan to Turin, the similarities in these situations are uncanny.

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Milan were not the force City have been in Serie A at the time, but they had just come off the back of a title-winning campaign when they let Pirlo walk out of the door.

The classy midfielder, spurned by the club he had served with distinction, then helped turn Juve into the most dominant force Italian football has ever seen.

No one had perhaps expected Pirlo to go for as long as he did at the top level at the time, but Juventus saw the potential and swooped in to make an incredibly shrewd signing.

De Bruyne of 2025 can perhaps be likened to the stature Pirlo held 14 years ago and although no two players are ever the same, Liverpool can take some lessons from how things ended up for the legendary Italian.
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