Alen Halilović, once hailed across Europe as the “Croatian Messi” and a generational prodigy, finds himself without a club at age 30 following the expiration of his contract with Eredivisie side Fortuna Sittard. Records show the midfielder’s career trajectory turned sharply downward after early milestones at Dinamo Zagreb and Barcelona, with subsequent stints across top European leagues failing to deliver sustained success.
Early Promise and Record-Breaking Ascent
Born on June 18, 1996, Halilović rose quickly through the ranks at Dinamo Zagreb, where he became the second-youngest player to debut in the UEFA Champions League. On June 10, 2013, at 16 years, 11 months, and 23 days old, he became the youngest player to debut for the Croatia national team, earning the first of his 10 senior caps against Portugal. That rapid development drew intense attention from elite European scouts, leading to a March 2014 transfer to Barcelona for an initial fee of 2.2 million euros.
In Catalonia, Halilović joined the club’s B team, making 30 appearances in his first season. Official club databases show he made two official appearances for Barcelona’s senior side, including a 28-minute substitute appearance in a 4-0 Copa del Rey victory over Elche on January 15, 2015. A subsequent loan to Sporting Gijón during the 2015-16 La Liga campaign proved more productive, yielding 36 appearances and 24 starts. However, permanent integration into Barcelona’s senior squad did not materialize, prompting a permanent transfer to Hamburger SV in 2016.
The AC Milan Stint and Gattuso’s Assessment
Following spells at Hamburg and Las Palmas, AC Milan acquired Halilović on a free transfer in the summer of 2018, signing the then 22-year-old to a three-year contract. Gennaro Gattuso, Milan’s manager at the time, personally contacted the player to outline a role in the squad. Yet, the anticipated revival in Serie A never materialized.
Halilović recorded zero appearances in Serie A, featuring only three times in the UEFA Europa League for a total of 60 minutes—55 minutes across two matches against Luxembourg’s Dudelange and five minutes against Olympiacos. Tactical misalignment contributed to the impasse. Gattuso favored a physically strong, defensively industrious midfield featuring players like Franck Kessié, Lucas Biglia, Tiemoué Bakayoko, and Giacomo Bonaventura. Halilović operated as an attack-minded playmaker whose tactical anarchy and reluctance to engage in defensive recovery clashed with the manager’s system. Gattuso publicly criticized the midfielder after a Europa League fixture for holding onto the ball too long and resisting quick distribution.
Upon moving to Standard Liège on loan in January 2019, Halilović addressed his lack of playing time, telling reporters that questions regarding his exclusion should be directed to the manager. By October 2020, Milan and the player agreed to a mutual contract termination.
Later Career Journeys and Current Status
The post-Milan phase of Halilović’s career involved several short-term engagements. He joined English Championship side Birmingham City in November 2020 before moving to Reading ahead of the 2021-22 season. A return to Croatia with Rijeka in July 2022 lasted only eight appearances before another contract termination in January 2023.
His longest recent tenure came in the Netherlands with Fortuna Sittard, where he spent three seasons. Following his 30th birthday on June 18, 2026, and the expiration of his contract on June 30, 2026, Halilović entered the free-agent market.
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