Carlo Ancelotti, the legendary Real Madrid manager, will stand trial Wednesday over allegations of tax fraud, marking the latest high-profile case in Spain’s relentless pursuit of undeclared earnings by football’s elite.

Prosecutors are demanding a four-year, nine-month prison sentence, accusing the 65-year-old Italian of failing to declare over €1 million ($1.1M) in image rights income between 2014 and 2015. The trial, set for Madrid’s High Court of Justice, is expected to last two days—but could end abruptly if a settlement is reached.

The Allegations: Shell Companies & ‘Hidden’ Income

Spanish authorities claim Ancelotti only reported his Real Madrid salary during his first stint as coach, despite being a tax resident in Spain. Investigators allege he used a “complex web” of shell companies—some based outside Spain—to obscure earnings from image rights and real estate.

A 2023 court document obtained by AFP revealed Ancelotti had “acknowledged” the tax discrepancies, raising speculation of a last-minute plea deal to avoid trial.

Precedent: Messi, Ronaldo, and Mourinho’s Cases

Spain has aggressively pursued football figures for tax evasion, with mixed outcomes:

• Lionel Messi & Cristiano Ronaldo: Convicted but avoided jail (suspended sentences).
• José Mourinho: One-year suspended sentence (2019).
• Shakira: Paid €7.3M in fines for a €14.5M case (2023).

Ancelotti has dismissed the charges as an “old story”, voicing confidence in his legal team.

The Italian is the most successful coach in Champions League history (5 titles, 3 with Real Madrid). A conviction could tarnish his legacy and jeopardize his second spell at Madrid, where he’s under contract until 2026.

What’s Next?

• Trial begins Wednesday at 10 a.m. CET.
• Possible settlement: Ancelotti may follow Mourinho’s path with a fine and suspended sentence.
• Real Madrid’s stance: Club yet to comment, but legal experts say a conviction could force tough decisions.