Andrés Nicolás D'Alessandro (born 15 April 1981) is an Argentine former professional footballer who played as an attacking midfielder.
Known as El Cabezón ("Big Head") for how large his big head looks on his small frame rather than any ego connotations, he won an Olympic gold medal with Argentina in 2004 and also played at that year's Copa América.
In 2020, he was awarded Brazilian citizenship.
D'Alessandro is regarded as one of Internacional's most notable players, alongside figures such as Falcão, Valdomiro, and Fernandão.
D'Alessandro was born in the La Paternal section of Buenos Aires, Argentina. He joined the labor force as a pizza delivery boy before becoming a professional footballer. He emerged through the River Plate youth system that has produced much of Argentina's top talent over the years. He followed the likes of Santiago Solari and Pablo Aimar through the ranks, together with Javier Saviola, with whom he shared the limelight in the 2001 Youth World Championship.
His talent attracted attention from European clubs following his success and performances at the 2001 FIFA World Youth Championship. He subsequently spent time on trial at West Ham in 2001 but no deal was agreed, with the management considering Joe Cole too similar and fee too high.
With the River Plate senior team, he won the 2001–02 and 2002–03 Primera División; the 2002–03 season was one of his best, scoring 15 goals in 40 appearances.
His 15 goals included several memorable performances, most notably River Plate's 5–2 victory over Rosario Central on 29 September 2002, when he scored twice and provided two assists. He also delivered an outstanding display on 8 June 2003, scoring once and grabbing two more assists in a 4–0 win against San Lorenzo.
In the 2003 Libertadores, he scored 4 goals, including a free kick in the round of 16 1st leg against Corinthians to help his team win the match 2–1.
Following continuing impressive performances, D'Alessandro eventually transferred to German Bundesliga club Wolfsburg in July 2003 for a club record €9 million. On 21 September 2005, D'Alessandro scored the Bundesliga's 40,000th goal since its creation in 1963, netting the fourth goal in a 4–2 victory over Hannover 96.
On 31 January 2006, to the surprise of most fans, D'Alessandro joined English Premier League club Portsmouth on loan for the remainder of the season. His main objective with his new club was to blend in with new teammates and help his club to avoid relegation. On Easter Monday, 17 April, he scored his first goal in English football – a contender for goal of the season – in Portsmouth's 2–1 defeat away to Charlton Athletic.
Portsmouth survived and manager Harry Redknapp sought to sign D'Alessandro on a permanent basis, but on 17 June 2006, he completed a season-long loan switch to La Liga outfit Real Zaragoza, citing his desire to play in Spain as a major factor in his decision. His club had a great season, finishing sixth in the league, qualifying for next years UEFA Cup, and narrowly being eliminated from the Copa del Rey quarter-finals to Barcelona on away goals. On 6 June 2007, he signed a contract at Zaragoza, keeping him at the club until 2011. However he suffered disciplinary problems in his second year at the club; he was involved in a heated altercation with teammate Pablo Aimar in training on 17 October 2007, and later stated that he felt coach Víctor Fernández was giving Aimar preferential treatment.
In 2008, despite expressing his desire to join River Plate, the club and the player were unable to come to an agreement. Shortly after, he joined his former River Plate manager Ramón Díaz at Argentine club San Lorenzo. Despite his short spell at the club, he became one of their most important players. One of his most memorable performances came on 8 May, in the second leg of the Copa Libertadores round of 16 match against River Plate; with San Lorenzo down 2–0 at the 60th minute, D'Alessandro was involved in both of his team's goals as they scored twice in 5 minutes to win 4–3 on aggregate. Shortly after the match, D'alessandro told reporters, "This victory is special because of the people directing the club, who made a mistake." He said this because of the failed attempt to return to River after leaving Wolfsburg.
However, after Díaz left the club, D'Alesandro opted to move to Brazil to play for Internacional and joined on 1 August 2008.
On 13 December 2008 it was reported on ESPN Deportes that the Los Angeles Galaxy had made a $10 million offer to for D'Alessandro but was declined.
He played an important role in Inter's 2008 Copa Sudamericana title, scoring 2 goals in the semifinal second leg against Chivas. In 2009 Internacional finished in second place in both the Brasileirão and Copa do Brasil. In 2010, D'Alessandro led Internacional to their second Libertadores Championship, and was elected the best player in South America for that year; in the 2010 FIFA Club World Cup, he also helped Internacional to a third-place finish, and was awarded the Bronze Ball as the tournament's third best player. In 2011 D'Alessadro had personally an even better year, but Internacional only managed to win the State Championship. 2012 was a bad year for both Internacional and D'Alessandro. Furthermore, rumours of him leaving to play in China caused a major distraction; after long drawn out drama he stayed but soon was injured. In 2013 his game improved again, and while Inter only won the State Championship, he was praised as the only positive factor of the team that year. 2014 started well; D'Alessandro continued to play well and led Inter to their 4th straight Gaucho Championship.
On 3 February 2016, he returned to River Plate after 12+1⁄2 years on a loan deal. He won his second Recopa Sudamericana and the Copa Argentina during his stay at the club. After that, he returned to Internacional de Porto Alegre for the 2017 season.
He scored in his last match as a professional, a 2–1 victory for Inter on 16 April 2022.