What does it take to win in the most complex deals on Wall Street — and in life?
In this Fireside Chat from the M&A Advisor's 2026 Distressed Investing Summit, former U.S. Secretary of Commerce Wilbur Ross joins Evan Hill, Partner at Cravath, Swaine & Moore, for a rare and candid conversation drawing from decades of high-stakes dealmaking.
Wilbur breaks down the difference between apparent risk and actual risk, why he walked out on Donald Trump mid-negotiation, and what today's young professionals are getting dangerously wrong. He also shares the three cardinal sins of negotiation — and why credibility is everything at the table.
🎙️ Risks & Returns: Creating Success in Business and Life
📍 Four Seasons Resort, Palm Beach, Florida
🏛️ Deal Forum | 2026 Distressed Investing Summit
📚 Wilbur Ross's book available now
SHOW NOTES:
Episode: Risks & Returns — Creating Success in Business and Life
Event: Deal Forum — 2026 Distressed Investing Summit | Four Seasons Resort, Palm Beach, FL
Host: The M&A Advisor | Roger Arnaldo
Guests:
- Wilbur Ross — Former U.S. Secretary of Commerce; legendary distressed investor; author of Risks & Returns: Creating Success in Business and Life
- Evan Hill — Partner, Corporate Practice, Cravath, Swaine & Moore
What You'll Learn:
Relationships: All business begins with a sale. Wilbur reflects on the mentors who shaped his career and why he wrote his book — to push back against a generation of young professionals with "fragile personalities" and low risk appetite.
Apparent vs. Actual Risk: The real edge isn't access to information — it's interpretation. What separates top investors is spotting the gap between perceived and actual risk. "Apparent risk you get paid for." Being a generalist made Wilbur dependent on specialists, and that dependence became a competitive strength.
The "Loser's Mentality": The hardest challenge in any turnaround is getting boards to replace the management that caused the bankruptcy. Distressed managers always blame outside forces — unions, China, regulators — and never themselves. Fresh leadership with industry-specific experience is often the single biggest lever.
Negotiation — The Cardinal Sins: Know your floor and the other side's hot buttons. Whoever is most willing to walk away wins. Start with easy points to build momentum. Never bluff — once called, you lose all credibility. Never lie. Never renege.
The Trump Taj Mahal Story: Wilbur was hired to recover losses on defaulted casino bonds trading at $0.20. Trump opened by saying bondholders should "just accept the $0.20." After hours of no movement, Wilbur walked out — using Trump's own pressure tactics against him. Months of negotiation followed. By October, a chapter 11 filing threat finally closed the deal. His mother called afterward, furious he'd made a deal with Trump — and never forgave him for not becoming a lawyer.
For the Next Generation: Every successful entrepreneur has failed. The ones who make it learn from the failure and find another path. A laundromat that failed in three months led its founder to pivot to generic pharmaceuticals — and straight onto the Forbes 400.
Book: Risks & Returns: Creating Success in Business and Life by Wilbur Ross
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