The December 2019 appointment of one of the most celebrated figures in world football as Everton manager marked the apotheosis of Farhad Moshiri’s ambition as Everton owner.

A multiple league title and Champions League winner across an array of clubs and countries, Ancelotti was a figure Evertonians hoped would bring back glory to Goodison. Alas, his appointment was undermined by the outbreak of the Covid-19 pandemic three months into his managerial reign and growing uncertainty behind the scenes at the club. His departure after just nineteen months presaged a new increasingly troubled era for Everton.

Born on June 10, 1959, in Reggiolo, northern Italy, Ancelotti's playing career was marked by his exceptional talent as a midfielder, beginning with his professional debut at Parma in 1976. His performances quickly caught the attention of bigger clubs, and by 1979, he had signed with Roma, where he would spend the majority of his playing career.

At Roma, Ancelotti became a central figure in a team that won the Serie A title in 1983 and four Coppa Italia trophies during the 1980s. His ability to dictate the tempo of a game, combined with his tactical intelligence and vision, made him a vital component of the Giallorossi’s midfield. He was also known for his leadership qualities on the pitch, eventually becoming the club’s captain. His playing career, however, was not without challenges. Ancelotti struggled with knee injuries that limited his appearances but did not diminish his influence on the field.

In 1987, Ancelotti moved to AC Milan, where he became part of one of the most iconic teams in football history under the management of Arrigo Sacchi. At Milan, Ancelotti played alongside some of the greatest players of the era, including Franco Baresi, Paolo Maldini, and Marco van Basten. With Milan, Ancelotti won two European Cups (now the UEFA Champions League) in 1989 and 1990, along with two Serie A titles. His time at Milan solidified his reputation as one of the finest midfielders of his generation. Ancelotti retired from playing in 1992, leaving behind a legacy of excellence and a deep understanding of the game that would later serve him well in his managerial career.

Ancelotti transitioned seamlessly from playing to management, quickly establishing himself as one of the most respected coaches in the game. He began his managerial career with Reggiana in 1995, leading the team to promotion to Serie A in his first season. This success led to a move to Parma, where he continued to build his reputation as a tactician. His big break came in 1999 when he was appointed as the manager of Juventus.

Despite not winning any major trophies with Juventus, Ancelotti’s methods and approach to management caught the eye of AC Milan, who hired him in 2001. This was the start of a golden period for both Ancelotti and Milan. During his eight years at the club, Ancelotti led Milan to numerous titles, including two UEFA Champions League trophies in 2003 and 2007, and a Serie A title in 2004. His calm demeanour, ability to manage star players, and tactical flexibility became his trademarks, earning him the nickname “The Professor."”

After leaving Milan, Ancelotti's managerial career took him across Europe’s biggest clubs, including Chelsea, Paris Saint-Germain, Real Madrid, and Bayern Munich. He won league titles in Italy, England, France and Germany, and in 2014, he achieved his long-standing ambition of winning “La Decima” with Real Madrid, securing the club’s 10th European Cup/Champions League title. Ancelotti's success on the European stage, combined with his unique ability to connect with players and adapt to different football cultures, made him one of the most sought-after managers in the world.

His appointment as Everton manager in December 2019 soon after leaving Napoli was seen as a major coup for the Merseysiders and was viewed as an unequivocal statement of intent. Ancelotti himself was attracted to the project of revitalizing a storied club and embraced the challenge with his characteristic calm and optimism.

‘In a way, Everton is an unusual coda to a career,” remarked the New York Times. ‘Most managers spend their early years at “project” clubs, trying to shape a middling power into a showcase of their talents, and then take their reward later on, in the form of the chance to take charge of one of the game’s superpowers. Ancelotti at Everton somehow inverts that pathway.’

Yet just three months into his Goodison tenure, in March 2020, the onset of the COVID-19 pandemic, closed the world – and football – down, while also posing unprecedented challenges for clubs everywhere. The season resumed behind closed doors in June, but it was a difficult period, particularly for Everton, as the absence of fans at Goodison left a funereal atmosphere. Despite these challenges, Ancelotti managed to steady a club that was on the slide after a difficult period under his predecessor, Marco Silva, and guide Everton to a twelfth-placed finish in the 2019/20 season.

The 2020/21 season, mostly played behind closed doors, saw Ancelotti bring in several key signings, including Colombian star James Rodríguez, who had previously played under him at Real Madrid. Ancelotti’s ability to attract high-profile players was one of the reasons Everton fans were so excited about his tenure. The season began promisingly, with Everton winning their first four league games and briefly topping the Premier League table. This early success led to renewed optimism that the club could challenge for European qualification.

However, as the season progressed, inconsistency became a problem for Ancelotti’s side. Injuries to key players, including James Rodríguez and Dominic Calvert-Lewin, as well as a lack of depth in certain areas, hampered the team’s progress. Everton’s form at an empty Goodison was particularly concerning, as they struggled to replicate their strong away performances at home. Ancelotti often spoke about the challenges of playing without fans, noting that the absence of the Goodison faithful made a significant difference to the team’s performances. In total Everton would play in front of meaningful Goodison crowds just five times under Ancelotti’s tenure, winning three and drawing two of these encounters.

Despite these challenges, Everton remained in contention for European qualification until the final weeks of the 2020/21 season. Ultimately, the club finished in tenth place, a slight improvement on the previous year but still below the expectations that had been raised by their strong start. Ancelotti’s time at Everton was characterized by moments of brilliance, such as a 2-0 win over Liverpool at Anfield, the club’s first victory at their rivals’ ground since 1999. However, the inconsistency that plagued the team’s performances meant that they often fell short. A defeat in his penultimate home game to an already relegated Sheffield United typified his spell in charge: the single result effectively cost them a European place.

Off the pitch, Ancelotti quickly became a beloved figure on Merseyside. He was known for his affable personality and ability to connect with people from all walks of life. Ancelotti and his family settled in Crosby, a coastal suburb of Liverpool, where they quickly became part of the local community. Ancelotti often spoke about how much he enjoyed living in the area and taking walks along the beach. His down-to-earth nature and willingness to engage with fans made him a popular figure not just among Everton supporters, but across the city.

Ancelotti’s departure from Everton in June 2021 came as a shock. He left the club to return to Real Madrid, a move that was difficult to turn down given his history with the Spanish giants and the allure of managing one of the world’s most successful clubs. Ancelotti's departure was met with disappointment by Everton fans, who admired the Italian and had hoped he would lead the club to greater success. Instead his departure precipitated a new, far more troubled era.

At Madrid, the Italian returned to what he did best: winning. There were LaLiga titles in 2022 and 2024, the same years he also lifted the Champions League for the fourth and fifth time as manager, and sixth and seventh times overall in his career. At Goodison, where Everton were dealing with successive relegation battles after his departure, such achievements seemed to make his time as manager an almost unimaginable passage in the club’s history.  

The legacy of Ancelotti’s time at Everton is mixed. While he brought a sense of optimism to the club, his tenure ultimately fell short of the expectations that had been set. In part, this was unavoidable, owing to the unprecedented circumstances the pandemic put the club into. Equally, the worsening financial situation behind the scenes was something supporters were largely unaware of at the time, and it is likely to have limited the extent that he was able to rebuild the team.  Yet Ancelotti's time at Everton also demonstrated his ability to adapt to different challenges and environments, further cementing his reputation as one of the most versatile and accomplished managers in football history.

 “They (Ancelotti and his family) loved Everton as a club and Liverpool as a city, so it was a loss to leave,” his physio, Danny Donachie, would recall of Ancelotti’s departure in a May 2024 interview with The Athletic. “But he was going back to Real Madrid. His club.”