Retro Football: 10 Photos Of Jimmy Greaves During His Brief, Ill-Fated Dalliance With AC Milan

Chris Wright

20th, February 2019

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The great Jimmy Greaves turns 79 today so we’re marking the occasion with 10 photos of the great poacher in his pomp.

Well sort of anyway. Indeed, already at the peak of his powers, Greaves left boyhood club Chelsea after seven years at Stamford Bridge to try his hand in Italy with AC Milan.

The key motivation was financial as, although the maximum wage had just been revoked in English football, Serie A was still incredibly flush by comparison.

It didn’t go well, with the prolific 21-year-old striker struck down by homesickness and regret before he’d even set foot on the plane.

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With a transfer from Chelsea to Milan pending, Jimmy Greaves sits down at home to inspect his nine England caps, 1961

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On the fence: Jimmy Greaves perches on the perimeter during a visit to the San Siro stadium in Milan, 1961

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Jimmy Greaves dons the famous red and black stripes for the first time at his maiden training session with Milan, 1961

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Jimmy Greaves holds his new club colours aloft (as well as a celebratory glass of Campari) after officially signing for Milan, 1961.

After going through in June, the £80,000 transfer temporarily made Greaves the most expensive British player in the world until Gerry Hitchens left Aston Villa to join Inter Milan for £85,000 just two months later.

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After getting cold feet about the prospect of leaving London behind, Greaves (seen here alongside Milan coach Nereo Rocco) actually attempted to cancel his move to Milan before it was made official, but the Italian club refused.

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He failed to settle and quickly fell out with Rocco, complaining that the Milan trainer had painted him as a “spoiled brat”.

Tensions came to a head during a game against Sampdoria in which Greaves lashed out at a defender who had spat at him. Samp scored an equaliser from the resulting freekick and Rocco placed the blame squarely on Greaves, who was subsequently fined almost £300 and transfer-listed for his ill discipline.

Alas, all those Italian lessons were to go to waste.

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Milan accepted two bids of around £96,000 for Greaves from Chelsea and Tottenham and he left to join the latter in December of 1961, just six months into his three-year contract. He left the Rossoneri having scored nine goals in 14 appearances.

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Jimmy Greaves runs out of the tunnel at White Hart Lane to great applause ahead of his league debut for Tottenham (against Blackpool), 15 December, 1961.

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The People newspaper advertise their exclusive interview with Jimmy Greaves in which the England striker gives a warts-and-all expose of his short and largely despondent time with Milan, 1961

Writing later in his autobiography, Greaves blamed his miserable dalliance with Milan with instigating and exacerbating the alcohol problem he continued to struggle with for the majority of his later life.

I can pinpoint the day, the hour, the minute, the second that I doomed myself to life as an alcoholic. It was the moment I signed my name on a contract that tied me head and foot to AC Milan.

Over a period of about a year, I was in a state of turmoil. Frightened, frustrated, bored, aggravated, depressed. All the classic ingredients that drive a man to drink.

Should you wish to learn more of the lasting impact Greaves’ career nadir had on his psyche, we thoroughly suggest you give Adam Bate’s brilliant IBWM article “Hell On Earth” a read.