Anna Wintour’s Former Partner Shelby Bryan’s Financial Struggles Preceding Their Separation!


The relationship between Anna Wintour and John “Shelby” Bryan was marked by both personal and financial challenges, adding complexities to their partnership. Here’s a breakdown of significant events and issues in their relationship:

Anna Wintour and John “Shelby” Bryan began their relationship after meeting in 1997. The affair gained public attention when they were spotted together in a compromising situation, leading to media scrutiny and speculation.

Following their affair, both Wintour and Bryan subsequently divorced their respective spouses and remained in a relationship for more than two decades.


John “Shelby” Bryan faced a significant financial downfall in the early 2000s due to a failed $750 million telecommunications deal. His company, ICG Communications Inc., experienced a sharp decline in stock value, leading to bankruptcy and Bryan’s ousting as CEO.

Bryan’s divorce from his former spouse Katherine resulted in financial strain. Katherine was set to receive profits from shared marital properties, including their townhouse in New York City and estate in East Hampton.

Bryan also faced financial issues related to unpaid property taxes owed to the IRS, totaling more than $1.2 million in 2013. He had been gradually paying off the debt but admitted challenges in settling the full amount due to financial constraints.

Reports suggested that Bryan’s financial difficulties might have contributed to the strain in his relationship with Wintour. Speculation arose that Wintour’s ambitions, coupled with Bryan’s financial woes, might have influenced their separation.

Sources hinted that Wintour’s dedication to her career and its demands might have played a significant role in their breakup, suggesting that her professional commitments often took precedence over their relationship.

While the exact reasons for their split might remain speculative, the financial challenges faced by Bryan, along with the demands of Wintour’s high-profile career, seemingly contributed to the complexities and eventual end of their long-term relationship.