David O’Reilly

Has Howard Hughes been playing offense or defense in the national housing market under shifting policies toward single-family housing? 

Offense. 

We’ve always believed the best defense is building communities where people genuinely want to live, regardless of what’s happening in the broader housing market. We’re not a traditional homebuilder. We develop the infrastructure, amenities, schools, commercial centers and public spaces that make a community desirable, and then sell finished residential land to the nation’s leading homebuilders. 

While housing affordability and interest rates certainly influence buyer behavior, the demand for great communities doesn’t disappear when the market becomes challenging. Our communities consistently command premium land values because of the quality of life they deliver. We’re playing the long game, and that gives us the confidence to continue investing when others might pull back.

If you could put a master-planned community in any market that you aren’t in already, what would it be? 

I’d look for exactly the same characteristics that have made our existing communities successful: a low-tax, business-friendly environment, a relatively low cost of living, a well-educated workforce, a warmer climate, proximity to major transportation infrastructure and a reasonable drive to a major city. Those characteristics aren’t accidental. They create an environment where businesses want to invest, employers want to locate, and families want to live. 

That’s the foundation of a successful master-planned community. We have decades of development opportunities within our existing portfolio, so I don’t anticipate entering a new market anytime soon. But, if we did, those are precisely the characteristics we’d look for.

How would you describe Howard Hughes’ investor base?

Historically, Howard Hughes has attracted investors who understand the tremendous long-term value embedded in our real estate portfolio and appreciate how that value compounds over decades. With Bill Ackman’s return as executive chairman and Pershing Square’s investment, we’re attracting a broader group of investors who recognize the opportunity to build a diversified holding company through disciplined capital allocation. 

Vantage is a great example. We’re now attracting investors who understand the economics of a well-run insurance business and recognize the extraordinary track record of Marc Grandisson, who helped build Arch Capital into one of the industry’s great success stories. 

What ties these investors together is a long-term perspective and an appreciation for exceptional businesses led by exceptional people.

Could you tell us about the cuts that you’ve made in your portfolio?

I wouldn’t necessarily characterize them as cuts. We’ve been very deliberate about evaluating which assets create the greatest long-term value for our shareholders. 

The separation of Seaport Entertainment Group was an important step in sharpening our focus. We also sold non-core multifamily properties in the Woodlands, where we believe we’ve already captured much of the value we set out to create. We’ll continue to monetize assets that have fulfilled their strategic purpose while retaining those that provide lasting competitive advantages.

There’s no prize for owning an asset forever simply because you developed it. The objective is to make sure every dollar of capital is working as hard as possible for our shareholders, while preserving the assets that make our communities extraordinary.

Can you tell us about any changes in Howard Hughes’ day-to-day since the Pershing investment in 2025?

At the Howard Hughes Holdings level, the biggest change is that we’re now thinking about capital allocation across a much broader universe of opportunities. Bill Ackman, Ryan Israel and the Pershing Square team bring tremendous investment expertise as we build a diversified holding company. 

At Howard Hughes Communities, our fundamental mission hasn’t changed. We’re still developing extraordinary communities, investing in infrastructure, and creating exceptional places to live and work. What is evolving is how we finance and own those assets. We’re increasingly looking at joint ventures and third-party capital to expand our development capabilities without relying exclusively on our balance sheet. It’s an exciting combination: the same long-term commitment to our communities, with a more flexible capital model that creates opportunities for growth.

What is the most unusual property in the Howard Hughes portfolio?

I’d point to Toro District, the 83-acre mixed-use district we’re developing in Bridgeland in partnership with the Houston Texans. Most people don’t immediately associate an NFL team’s headquarters and training facilities with a master-planned community developer. But, for us, it makes perfect sense. We’re not simply creating a place for a football team to practice. We’re developing an entire district with sports, entertainment, restaurants, retail and public spaces that will bring people together throughout the year. The Texans are an extraordinary partner, but the bigger opportunity is creating a new center of gravity for Northwest Houston. 

That’s what we do. We create places that become much more valuable than the sum of their individual parts.

Lightning Round:

Your AI platform of choice? ChatGPT (behind our firewall). One of my most productive employees, and it never asks for a raise.

Who would play you in a movie? Jason Statham. He’s mastered looking calm when everything around him is falling apart.

One prompt you’d never give AI. “Tell me what I want to hear.”

Jalen Brunson or Aaron Judge? Neither. I’m a Boston sports guy.

“Oppenheimer” or “Odyssey”? Haven’t seen either.

Tom Holland, Andrew Garfield or Tobey Maguire? Animated Spidey.

Have you ever eaten pizza with a knife and fork? Never.

The most money you’ve ever spent on a hamburger? Whatever chef Noah’s burger costs at the Fulton in the Seaport District. Still can’t believe I ordered a burger at one of Jean-Georges’s great seafood restaurants, but it was outstanding.

Bank or non-bank? Depends on the cost of capital.

Last book you read? The Essays of Warren Buffett edited by Lawrence A. Cunningham.

Borrowing costs — up or down in 2027? Down. Eventually, the Fed will agree with me.

What was your nickname growing up or starting out? Never had one.

How long before AI kills us all? Hopefully, after I retire.

Where’s your secret escape compound? If I told you, it wouldn’t be much of a secret.