JPC Podcast 12: Robert Deckey on Distress Cycles, Multifamily Refinancing & Market Recovery

Robert Deckey on Distress Cycles, Refinancing Pressure & Finding Opportunity at the Bottom

In this episode of Confronting the Impossible, Leo Jacobs welcomes Robert Deckey, a veteran of over three decades in distressed real estate investing.

From launching REIT IPOs during the S&L crisis to navigating the Global Financial Crisis, and now identifying opportunity in multifamily refinancing, Deckey brings one powerful message:

Markets are cyclical.
Opportunity lives at the trough.
Discipline determines survival.

Lessons From the S&L Crisis

Deckey’s career began in the middle of financial chaos.

The S&L crisis taught him early how quickly values can collapse - and how government policy, lender sophistication, and capital markets evolve over time.

In the 1990s, distressed assets were sold quickly.
Today, lenders are more patient. More strategic. More sophisticated.

That means fewer “flash sales.”
But it also means distress doesn’t disappear - it simply changes form.

The Current Impossible: Multifamily Refinancing

Today’s pressure point isn’t office alone.

It’s multifamily refinancing.

Over the next three years:

• Billions in multifamily loans are expiring
• Many properties were financed at 3–3.5% interest rates
• New rates sit closer to 5.5–6%
• Property values in many markets are down 20%

The result?

Loan-to-values that have shifted from 65% to 80% or higher.

Developers are not necessarily bad operators.
They are caught in a rate cycle.

And that creates a void.

The Strategy: Lending at the Trough

Deckey’s thesis is simple:

You don’t lend at the top of the market.
You lend when values are down.

With construction pipelines slowing and supply shrinking, multifamily fundamentals may stabilize over the coming years.

The opportunity lies in:

• Underwriting strong borrowers
• Lending at conservative loan-to-value ratios
• Structuring bridge financing
• Allowing operators time to execute their business plans

It’s not about gambling.

It’s about timing, underwriting, and patience.

The Shift From Financial Engineering to NOI Growth

One of the most important themes of this episode:

The 30-year run of cap rate compression is over.

For decades, falling interest rates boosted asset values.
That tailwind is gone.

The next decade belongs to operators who can:

• Grow NOI
• Manage expenses
• Improve occupancy
• Operate efficiently

Returns will come from fundamentals - not financial engineering.

The Psychological Side of Distress

This episode goes beyond numbers.

Leo challenges Deckey on borrower psychology.

Are today’s distressed borrowers failures?

Not necessarily.

In many cases, they are disciplined operators trapped between:

• Interest rate spikes
• Government regulation
• Market overbuilding
• Capital tightening

The impossible today is often external - not internal.

Survival requires partnership, timing, and liquidity.

Final Takeaway

Distress is not new.

Cycles are not new.

But the market is more efficient, more competitive, and more sophisticated than ever.

There will be fewer “easy” distress wins.

Success will require:

Discipline.
Underwriting rigor.
NOI growth.
And patience.

🎧 Watch Full Episode

Watch Full Podcast 12 with Robert Deckey for a masterclass on cycles, refinancing pressure, and finding opportunity when the market feels impossible.

PODCAST - Confronting the Impossible with Leo Jacobs.

Leo Jacobs, Founder and CEO of Jacobs PC

Known for finding creative, expedient solutions to complex and high-profile cases, Leo excels in matters including distressed investment and asset management, real estate law, corporate law, dispute resolution, business divorces, negotiation, and more. Leo’s extensive expertise in debt and equity structures enables him to employ a full spectrum of legal tools to achieve swift, optimal results for clients. His practice, Jacobs P.C., bridges commercial litigation, corporate transactions, and financial rehabilitation, handling cases across federal, state, and bankruptcy courts, as well as administrative tribunals.

If you would like to join the podcast email requests to pr@jacobspc.com