It was December 1961 and Jimmy Greaves had just introduced himself to an adoring White Hart Lane crowd by scoring a hat-trick on his Tottenham debut in a 5-0 victory over Blackpool. The goals were the first of the 266 Greaves would register on his way to becoming the club’s finest goalscorer and represented a glorious return to English football following a turbulent spell in Serie A with AC Milan.
Before becoming the darling of N17, Greaves had already demonstrated his spectacular scoring capabilities in west London at Chelsea. A predatory, ruthless finisher who possessed pace and the ability to dribble past opponents with ease, Greaves made his debut as a 17-year-old at Stamford Bridge where he would go on to score 132 times. The England striker was the club’s top scorer in each of those seasons, including an incredible return of 43 goals in the 1960/61 campaign.
While Greaves’ phenomenal goal return brought wide acclaim and an England call-up, the glory and trophies that the frontman craved eluded him as Chelsea struggled to maintain consistency in England’s top flight. Following his eye-catching 1960/61 season, Greaves felt the time had come to depart Stamford Bridge and sought a new challenge that could help bring him silverware. Double winners Tottenham made their interest clear, but Chelsea were adamant they would not sell to their fierce rivals.
Greaves’ reputation as a striker of rare pedigree had spread across Europe, and in the summer of 1961 AC Milan acted quickly to ensure Greaves would go on to grace the San Siro. The Italian giants sent over their negotiator, Gigi Peronace, a man Greaves later described as “looking like he was a cast member of the Godfather”, to broker the deal. The charismatic representative quickly charmed Greaves and a deal for £80,000 to sign him was swiftly agreed.
The move was seemingly perfect for all parties. The transfer fee Chelsea would receive for Greaves would ease the financial concerns they were carrying while the England man would have a realistic opportunity to add trophies to his staggering goal return. Another motivation for Greaves, who was earning £20-a-week at Chelsea, was the new riches that awaited him in Italy. After passing a medical, he was informed by his new manager, Giuseppe Viani, that he would be receiving the equivalent of £130-a-week along with a luxurious penthouse to share with his wife Irene.
However, with everything set in place for his departure to the continent, doubts began to develop in Greaves to the extent that he attempted to have the deal annulled. Greaves informed Chelsea of his intention to stay but the cash-strapped Blues were eager for the move to materialise. “My initial euphoria about the prospect of playing and living in Italy quickly subsided and, as the weeks passed, I began to have doubts about the move. I liked my creature comforts. I enjoyed London life and the London lifestyle,” the striker later recalled.
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After completing a tour with the national side at just 21, Greaves was set for a new adventure in Serie A. The journey, however, wasn’t to go entirely to plan. Two hours before his scheduled departure for Italy, Greaves was joined at Heathrow by Daily Express reporter Desmond Hackett.
Hackett proposed a celebration was in order and the pair proceeded to embark on a lobster and champagne lunch. After two hours of indulgence in fine dining and football conversation, Greaves realised that he had missed his flight. He subsequently boarded the next available departure and landed in Italy six hours late and a little worse for wear following further joviality on the plane.
The episode represented the first of several disputes Greaves would go on to have with the Milanese giants. Shortly after his arrival, Greaves flew back to England to be with his wife who was due to give birth to their daughter, and the striker insisted on staying with Irene and their newborn for a few days. Milan saw things rather differently and fined the striker £50 for every extra day he stayed in London.
When Greaves did travel to Italy, however, he didn’t fly directly to Milan and instead set off for Venice where he had arranged a boot sponsorship deal with Vallesport. When Greaves did arrive in Milan for pre-season training a day late, he learnt that Viani, the manager so keen on signing Greaves, had suffered a heart attack and would step aside for another to take charge of the Rossoneri.
Viani’s replacement would be Nereo Rocco, and there was friction between the two from the start following Greaves’ detour to Venice. Greaves had been accustomed to a more relaxed way of life in England, and Rocco’s intense, disciplinarian approach was a shock to the system of the young England star. “He made my life hell and I didn’t exactly bring sunshine into his. He was a strict disciplinarian who could have given irritability lessons to Captain Bligh,” Greaves would later recall.
Rocco was a strict taskmaster who would have control over Greaves’ meals and sit opposite him while he ate to ensure he finished them. Smoking, unsurprisingly, was seen as a habit unbefitting of a professional footballer in the eyes of Rocco. Greaves’ desire for a cigarette would be increased by the stress of his new life and the forward would sneak into the training ground bathroom to smoke where he would often discover that several of his teammates had shared the same idea.
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While Greaves struggled to adapt to Rocco’s demands, the professionalism he experienced at Milan was also in stark contrast to the facilities he had grown accustomed to at Chelsea. Greaves arrived to find a state-of-the-art training complex that included a restaurant and mountain retreat whereas, back in London, Chelsea would train behind the goals on a dog track. Stamford Bridge was a fairly large stadium but Greaves would now be playing in front of 87,000 passionate Italian fans in the cauldron that is the San Siro.
Everything surrounding Greaves’ arrival in Milan had been chaotic and stressful but he knew that he could find solace in scoring goals. The England forward would finally make his Serie A debut against Lanerossi Vicenza and predictably he made it a scoring start. Greaves played alongside the finest striker in Italy at the time, José Altafini, who would be the main forward.
Greaves, meanwhile, was required to track back or be pushed out the wings to accommodate his teammate. He was subjected to tight marking that he wasn’t accustomed to in the First Division but the England man continued to score frequently, including a strike against bitter rivals Inter in the derby. The Milan side of 1961 also included the talents of Gianni Rivera, Giovanni Trapattoni and Cesare Maldini as the Rossoneri battled for the Scudetto.
Despite demonstrating the remarkable goalscoring prowess that he had built his reputation on, Greaves remained homesick and miserable. The goals certainly didn’t seem to be endearing him with Rocco either, as was evident in the aftermath of a 2-2 draw with Sampdoria.
Greaves had scored Milan’s first and assisted the second but he was to incur the wrath of Rocco for his involvement in Sampdoria’s late equaliser. He reacted to being spat in the face by an opposing defender by lashing out at the culprit. The resulting free-kick earned the Genoese club a point, leading Rocco to vent his anger at Greaves back in the dressing room where he branded the striker a disgrace to the red and black shirt.
The isolated striker could at least find comfort knowing that other Brits playing in Serie A were also struggling to adapt to the new culture. Gerry Hitchens was in the same city playing for Inter while Denis Law and Joe Baker were based west of Milan with Torino. Law and Baker shared Greaves’ disdain for Serie A, with events taking a turn for the worse when they collided into a lampost in the Alfa Romeo that Baker was driving. It was a crash that left Baker fighting for his life.
Law and Baker spent the majority of their time in their Turin apartment as they attempted to evade the attentions of the Italian press, while the media scrutiny also proved too much for Greaves. “Both the English and Italian press wrote stories about me that were less than complimentary,” Greaves later recalled. “The Italian press were particularly vindictive making me out to be a spoiled brat.”
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Depression began to engulf Greaves as he also struggled to enjoy life on the pitch due to the defensive catenaccio system that Milan deployed. Although he continued to score goals, the defensive gameplan that relied on counter-attacking meant he would endure long periods without seeing the ball. An abundance of goals were being scored in the First Division in this era, but in Serie A matches were tight affairs with the Italian sides demonstrating their defensive mastery.
As the season went on, it became apparent that Greaves’ time in Italy would come to a premature end. The tension between Greaves and Rocco remained, and Milan began to prepare for life without the England forward by bringing in Brazilian Dino Sarni. Sarni was earmarked to play alongside Altafini, and Greaves was informed soon after that he had been placed on the transfer list. Two days later, Greaves’ wife Irene received a knock at the door of their Milan apartment where, on the other side, stood the man who would offer the striker a return to England that paved his way to footballing immortality.
Greaves arrived home to find Tottenham manager Bill Nicholson sat in his living room. Nicholson wanted extra firepower to boost his forward line for the team that was coming off the back of a triumphant season in which they had been crowned league and FA Cup double winners. Although Chelsea, too, were interested in bringing Greaves back to Stamford Bridge for a hero’s return, Greaves was exhilarated at the prospect of joining Tottenham.
After just 13 matches and four months on the continent, Greaves would return to English football for a sum of £99,999, a fee decided upon by Nicholson as a way of relieving Greaves of the extra pressure in becoming the country’s first-ever £100,000 signing. Following his outstanding performance in the defeat of Blackpool, Greaves would go on to gain legendary status at Tottenham as he produced a stellar career in which he became arguably the greatest goalscorer England has ever produced.
The 366 league goals that Greaves scored over his club career was a record in Europe’s top five leagues that stood for decades until Cristiano Ronaldo finally surpassed Greaves’ total in 2017. Sadly, only nine of those strikes arrived during his stint in the red and black of Milan, and Italian supporters, despite being overjoyed at securing the Scudetto following his departure, had been deprived of seeing Greaves at his scintillating best.
At just 21, the move to a new country and adaptation to a new culture may have simply arrived too early for Greaves. The striker never apportioned the blame for his failure to settle in Italy to Milan or Rocco and acknowledged that his heart was just not in the move from the start. He did, however, attribute the period as being a vital experience that helped him mature into an even better player than before: “I always felt I went to Milan a boy and came back a man.”
By Aaron Attwood @ajattwood