Double Diamond Investment Group

James Dondero makes the final investment decisions. Dondero co-founded Highland Capital Management in 1993 and previously built the guaranteed investment contract business at Protective Life. His investment committee at the family office draws on the same Dallas-based team that sources deals for the NexPoint platform, which he also controls through NexPoint Advisors. No external co-CIO or investment committee members have been publicly disclosed.

The office benefits from the origination network of NexPoint, Dondero's affiliated alternative-asset manager, which runs public REITs, interval funds, and private credit vehicles with over $16 billion in combined assets as of 2022. Distressed bank portfolios, restructured CMBS, and direct real estate acquisitions flow through a Texas-based team that has operated in the structured-credit market for three decades. This gives the family office access to institutional-scale deal flow without commingling its proprietary positions with fund investor capital.

Double Diamond is James Dondero's single-family office, but it operates in unusually close proximity to NexPoint, the regulated investment advisory firm Dondero also controls. The two entities share deal-sourcing, legal, and tax resources, but Double Diamond's positions are wholly proprietary and not held within any external fund structure. This hybrid arrangement allows the family office to piggyback on institutional origination while maintaining permanent, unconstrained holding periods.

The firm is stage-agnostic and event-driven. It allocates primarily across distressed and high-yield credit, commercial and residential real estate, and public and private equity. A recurring template involves acquiring restructured companies or real estate through debt-to-equity conversions, then managing them as operating positions. The office has historically favored Sun Belt markets — particularly Texas, Florida, and the Mountain West — where its real estate and credit teams concentrate their origination.

James Dondero co-founded Highland Capital in 1993, eventually building it into a $40 billion credit and hedge fund platform before stepping away from day-to-day management following a multi-year bankruptcy restructuring that concluded in 2023. He established Double Diamond separately in 2000 and later founded NexPoint Advisors, which now manages a suite of publicly traded REITs and private vehicles. Double Diamond and NexPoint share resources but are legally distinct — the family office's positions are proprietary, while NexPoint's are client assets.

Dondero has historically directed philanthropic giving through the family office and previously through Highland Capital's foundation. No dedicated Double Diamond philanthropic entity has been publicly disclosed as of 2024. Charitable activity appears to be handled on a deal-level or personal basis rather than through a separately named foundation tied specifically to the family office.

The family office prefers control-oriented positions and has rarely been documented co-investing alongside unaffiliated external managers. When third-party capital is involved, it typically flows through NexPoint's regulated funds, with Double Diamond taking a proprietary parallel position rather than a minority LP stake. The firm's public-record track record suggests a strong preference for originating and leading its own deals rather than joining syndicates.