Early years / Tenerife Born in
Adrogué,
Buenos Aires Province, Redondo played his first game in the
Primera División at only 16 for
Argentinos Juniors, and remained five years with the team before moving abroad to Spain. Redondo made his debut in
La Liga with
CD Tenerife, under the management of countryman
Jorge Solari. During this period,
Real Madrid twice lost the league title to arch-rivals
FC Barcelona on the final day of the season, in matches against Tenerife who were managed by
Jorge Valdano and, when the coach was appointed at Real Madrid in the summer of 1994, the player also made the move for a fee of
US$5 million.
Real Madrid The key years of Redondo's career were spent at Real Madrid, where he won two league championships and the
UEFA Champions League in
1998 and
2000. During the second victorious campaign in the latter competition, his performances won him the competition's
Most Valuable Player award, with new coach
Vicente del Bosque utilising him in a midfield combination with
Steve McManaman. In the quarter-finals against
Manchester United at
Old Trafford, he was the author of a spectacular play in which he
dribbled past
Henning Berg by backheeling the ball around him, recovering it and assisting
Raúl for his side's third goal (3–2 win, 3–2 on aggregate); after the game, opposing manager
Alex Ferguson said "What does this player have in his boots? A magnet?”. For his performances, he was subsequently voted the Champions League and
UEFA Club Footballer of the Year. During his time in Madrid, Redondo earned the nickname
El Principe ("The Prince"). In April 2013 he was named by daily newspaper
Marca as a member of the "Best foreign eleven in
Real Madrid's history", and four years later was selected by its readers to the club's all-time XI; during one full decade, he amassed Spanish top division totals of 268 games and 12 goals.
AC Milan In 2000, Redondo transferred to
Serie A club
A.C. Milan in a controversial
£11m move: he stated that he was not involved in transfer discussions and expressed his desire to stay at Madrid. In response, a section of Real Madrid supporters gathered outside the
Santiago Bernabéu Stadium protesting the transfer. However, he suffered a serious knee injury in one of his first training sessions for his new team, and was unable to play for the next years; he suspended his £2.74m-a-year salary, and even tried to give back the house and car which the Milan board had given him. Redondo did manage to contribute (albeit in a peripheral role) to Milan's successes in the
2002–03 and
2003–04 seasons, making a combined 16 league appearances and adding five in the
2002–03 Champions League and six in
the same edition of the
Coppa Italia, including the
two-legged final. In late 2004, at the age of 35, he retired from professional football following another knee injury. ==International career==