I rejected Tottenham transfer because of Arsenal – joining them would have been treason

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A footballing icon compared a potential transfer to Tottenham Hotspur to committing a criminal act

Fasika Zelealem Senior Sports Reporter

07:00, 22 Feb 2026

Transferring to a rival club is an occurrence in football that is traditionally frowned upon by fans, and rightly so.

In the case of iconic AC Milan defender Alessandro Costacurta, it was his love of Arsenal that stopped him signing a contract to become a Tottenham Hotspur player. A veteran of 21 years for the Italian giants, the 59-year-old won seven Serie A titles and the Champions League five times.

Given his status as one of the world's best defenders during his career and Milan's downturn in fortunes in the mid-90s, the opportunity for Costacurta to seek pastures new was available several times.

In particular, a move to the white half of north London was a potential reality after he spoke to then-Spurs boss Gerry Francis in 1996 about making the stunning move from Milan to London.

Costacurta - who retired in 2007 after his Champions League final victory over Liverpool - said in 2016 ahead of AC Milan vs Arsenal legends match that a transfer to Spurs never came to fruition because of his life-long love for the Gunners.

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"The idea of living in London was very exciting," Costacurta said to Arsenal.com. "But I finally refused and you know why? Because I couldn’t betray my English love. The truth is that I’ve been a keen Arsenal fan since my childhood, and playing for ‘our’ bitter rivals would have been high treason.

"When I was younger I liked the Arsenal shirt, the stadium, and some of the players from the 1980s such as Liam Brady. And I’ve always gone against the tide. All my friends were Manchester United or Liverpool fans, so I picked Arsenal and I’ve never changed my mind."

With 24 major honours to his name, it was surprisingly his experience playing at Highbury in the 1995 Cup Winners’ Cup that he chose as one of the best moments of his legendary career.

He explained: "The first game is possibly one of the favourite matches of my entire career. Not so much because of the game itself, which was very intense but perhaps not very exciting as the final score was a 0-0 and the only time we were really under threat was at set pieces.

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"It was more for the setting of Highbury. [The] Emirates is wonderful and over time it will gain its own mythical aura, but Highbury was unique.’ The two bitter rivals clash at the Tottenham Hotspur Stadium on Sunday afternoon in the second north London derby of the season.

The Gunners currently possess bragging rights after thrashing Spurs 4-1 in the reverse fixture as new interim boss Igor Tudor hopes to make the ultimate start during his reign in the capital.

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