Even the most cherished assets can become silent drains on wealth. The key is knowing when to hold and when to rebalance.
For ultra-high net worth families, certain assets are more than financial holdings; they are symbols of history, identity, and generational pride. But what happens when the markets for these legacy assets begin to shift? Failure to distinguish between sentimental and strategic value can allow cherished holdings to quietly erode liquidity and long-term growth potential.
The Shifting Definition of a Trophy Asset
This shift from asset to liability is often subtle. A vivid illustration can be seen in the recent 2025 Monterey Car Week auctions. Total sales were very strong at $432.8 million (the 2nd highest total ever and up nearly 10% year-over-year)—but the real story is one of changing tastes.
The takeaway isn’t the total value, but where that value came from. Collectors did not flock to the mid-century icons that defined previous generations. Instead, modern supercars accounted for nearly 40% of the total sales value.
Yesterday’s trophy assets are still blue-chip, but their audience is narrowing and their liquidity is at the same time far less certain.
A Pattern of Illiquidity
This pattern is not limited to collectibles. It reflects a broad re-evaluation of what defines a valuable holding, with similar trends evident in a range of major UHNW asset classes.
We see it in high-end residential real estate, where sprawling, half-finished multi-million dollar properties languish on the market, taking 400% longer to sell than median-priced homes. Driven by outdated assumptions and burdened by rising financing costs, many of these projects have become symbols of miscalculated capital. As selling times stretch and discounts grow, tying up capital in these projects has moved from a calculated risk to a meaningful liability.
The same liquidity crunch is impacting private equity, a longstanding foundational piece of UHNW portfolios. The LP and GP secondary market has nearly tripled in size over the past five years, reaching an estimated $175 billion in 2025. This surge is not driven by portfolio company failures, but rather reflects the mounting demand for liquidity as investors contend with increasingly unpredictable holding periods.
Simultaneously, the industry is showing signs of strain at a structural level. The SEC has made way for non-UHNW investors to allocate more to the asset class, a move seen as an attempt to attract new capital when funds are struggling to deploy it effectively. For existing investors, these trends are a clear warning: the dynamics that once made private equity a reliable engine of growth are becoming far more complex.
The New Geography of Wealth
Complicating the picture further is the changing geography of opportunity. Wealth has migrated toward regulatory stability, favorable tax regimes, and asset-friendly jurisdictions. We are seeing an unmistakable trend from London to Dubai and from New York to Singapore: there is greater focus then ever before on splitting holdings between asset classes and jurisdictions.
UHNW families must continue to expand their footholds in multiple global markets—not only to protect against policy risk but to access the next generation of growth.
From Stewardship to Strategy
Trusted advisors play a critical role in navigating this rapidly changing landscape. The imperative is no longer to simply manage assets and generate an attractive, risk-adjusted return. It is about keeping legacy assets top-of-mind and anticipating when they may become liabilities, so you can craft nimble, smart liquidity strategies.
At Leyster, we often engage when conventional answers fall short. Our clients are not selling their legacies. They are rebalancing them, quietly, decisively, and with an eye on tomorrow. We engineer discreet capital solutions relying on the assets others overlook. In doing so, we offer more than liquidity; we offer the power to choose when and how to act.
For UHNW families, maintaining this optionality is the new benchmark for intelligent wealth stewardship. If today’s prized assets no longer serve tomorrow’s goals, the time to act is now.