Could Benfica actually land Rafael Leao from Milan...

Benfica have emerged as one of the most concrete suitors for AC Milan winger Rafael Leao as the Portuguese international signals his desire for a new challenge ahead of the summer transfer window. The Eagles are monitoring the 27-year-old closely, with reports indicating that new bench boss Marco Silva is an avid supporter of such a move. AC Milan, under new manager Ruben Amorim, appear open to a sale after a disappointing campaign and have lowered their asking price to around €50 million.

Leao’s potential homecoming carries deep sentimental value. Born in Almada in 1999, the talented forward nearly joined Benfica’s academy as a youngster. He signed with the club but was left devastated when promised transportation failed to materialize, leading him to crosstown rivals Sporting instead. After progressing through Sporting’s academy, he made his senior debut in 2018, scoring once in four Primeira Liga appearances and winning the Taca da Liga. Leao moved to Lille in 2018. There, he impressed with 8 goals in 26 Ligue 1 matches during the 2018-19 season.

In 2019, AC Milan secured his services for €49.5 million. Leao blossomed into a star, playing a key role in their 2021-22 Serie A title triumph and earning the league’s MVP award in the process. Known for his explosive pace, dribbling and versatility on the left wing, he has become one of Europe’s most dynamic attackers. In the 2025-26 season, Leao recorded 9 goals and 3 assists in 29 Serie A appearances, plus adding another goal in the Italy Cup and appeared in 1,968 minutes of action across all competitions.

Any deal to Benfica would set a club record fee for the acquisition of a player but a player of Leao's skill set would be a boom for the Lisbon side and send a major statement to the league of the club's intent to return to the top of Portugal. Leao would get the fresh start his is looking for near family after seasons away from his homeland. Whether the move materializes remains to be seen, but interest from his boyhood club adds intrigue to the summer market and places other league club's on notice and we are sure someone will pick up Leao this time around.