The biggest issue stemming from Chelsea's historical financial discrepancies revolves around the potential for reputational damage and the erosion of trust in the club's management and governance. The recent charges brought by the Football Association (FA), totaling 74 breaches of agent regulation rules between 2009 and 2022, have cast a shadow over the club, despite the self-reporting of these issues by the new ownership group.

The sheer number of alleged breaches is a significant concern. These charges relate to payments made to agents and third-party investment rules, specifically over transfers including players such as Samuel Eto'o, Eden Hazard, and Willian. Such widespread and prolonged discrepancies suggest a systemic issue within the club's financial operations during the Roman Abramovich era. Even though the new ownership self-reported these issues, the scale of the problem inevitably raises questions about the club's past conduct and its commitment to financial fair play.

Reputational damage extends beyond just the club's image. It can impact relationships with sponsors, partners, and even fans. Sponsors may become hesitant to associate with a club facing serious allegations of financial misconduct, potentially leading to a decrease in revenue. Similarly, tarnished reputation can affect the club's ability to attract top players and staff, as individuals may be wary of joining an organization with a questionable ethical record.

Furthermore, the historical discrepancies could lead to a loss of trust among fans. Football supporters are passionate about their clubs and expect them to operate with integrity and transparency. Discovering that their club may have engaged in questionable financial practices can be deeply disheartening, potentially leading to disillusionment and a decline in fan support.

The self-reporting by the new ownership group, led by Todd Boehly and Clearlake Capital, is a crucial factor in mitigating the potential damage. By proactively disclosing the discrepancies to the relevant authorities, including the FA, the club has demonstrated a commitment to transparency and accountability. This proactive approach could influence the severity of any potential sanctions imposed by the FA.

However, the investigation and resolution of these charges could be a lengthy and complex process. The FA will need to thoroughly investigate each alleged breach, gather evidence, and determine the appropriate course of action. This process could take months, or even years, during which time the club will continue to face uncertainty and reputational risk.

Ultimately, the biggest issue arising from Chelsea's historical financial discrepancies is the challenge of rebuilding trust and restoring the club's reputation. While the new ownership has taken commendable steps to address the past issues, the road to full recovery may be long and arduous. The club will need to demonstrate a sustained commitment to ethical conduct, financial transparency, and good governance to regain the confidence of its stakeholders and ensure a positive future.