Italy pursues criminal trial against Amazon managers despite €527m tax settlement

Italian prosecutors are seeking to bring four managers of Amazon to trial in a high-profile tax case that could reshape how personal liability is applied to executives overseeing digital marketplaces in Europe.

The request, filed by prosecutors in Milan, relates to alleged value-added tax (VAT) evasion estimated at around €1.2bn linked to online marketplace sales in Italy. The case stands out because it continues even after Amazon reached a substantial tax settlement with Italian authorities.

Legal experts say the move signals a shift in regulatory strategy — from targeting corporations alone to pursuing potential criminal responsibility for individual decision-makers.

Criminal charges despite corporate settlement

In December, Amazon’s European unit agreed to pay €527m, including interest, to Italy’s Revenue Agency to resolve a dispute over VAT liabilities connected to third-party sellers using its marketplace.

Such agreements have historically closed the chapter on related criminal investigations in Italy. Once a company settles with tax authorities, prosecutors have typically ended proceedings through plea deals or case dismissals.

However, Milan prosecutors have opted to continue their investigation and have now asked a judge to allow criminal proceedings against both the company’s European entity and four of its managers.

A preliminary court hearing will determine whether the case moves forward to a full trial or is dismissed.

Allegations linked to marketplace sellers

The investigation centres on sales conducted through Amazon’s online marketplace between 2019 and 2021.

Prosecutors allege that the platform’s operational systems and algorithms enabled thousands of sellers based outside the European Union — many reportedly located in China — to sell products to Italian consumers without properly identifying themselves to tax authorities.

According to investigators, this structure allowed some merchants to avoid paying VAT on transactions carried out in Italy.

Under Italian tax law, digital platforms that facilitate sales may be held jointly liable for unpaid VAT when non-EU sellers operate through their marketplace.

Rising focus on executive accountability

While large companies frequently face tax disputes, the decision to pursue individual managers marks a notable development.

Regulators across Europe are increasingly examining whether executives responsible for designing and managing digital platforms can be held personally accountable when compliance failures occur within complex online ecosystems.

In this case, prosecutors appear to argue that managerial oversight of Amazon’s marketplace model may have contributed to the alleged VAT avoidance.

If courts allow the case to proceed, it could establish an important precedent on how responsibility is assigned inside global technology companies.

Potential impact on the European platform economy

Because VAT rules are largely harmonised across the European Union, the case could have implications beyond Italy.

Online marketplaces operating in Europe may face growing pressure to strengthen oversight of third-party sellers and ensure tax compliance across their platforms.

The Italian economy ministry has been listed as the injured party in the prosecutors’ filing, highlighting the potential scale of the alleged losses.

Amazon response and broader investigations

Following the December settlement, Amazon said it would “forcefully defend its position” in what it described as an unfounded criminal case.

The company also warned that prolonged legal proceedings and regulatory unpredictability could affect investment decisions in Italy.

The case is part of a broader wave of regulatory scrutiny facing the company in the country.

The European Public Prosecutor’s Office is currently investigating similar alleged VAT offences covering the period from 2021 to 2024.

Separately, Italian prosecutors are examining other matters related to the company’s operations, including possible customs fraud linked to imports and questions over whether Amazon maintained an undeclared permanent establishment in Italy.

A test case for platform governance

For legal analysts and technology companies alike, the Milan investigation may become a defining test of how European authorities address accountability in the digital economy.

If the case moves forward, it could mark a turning point in enforcement strategy — one where executives responsible for platform governance face the same scrutiny as the companies they lead.

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