Office Landlord During the Great Depression or Today—Which Era Is Worse?

Rooftop
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This might be the toughest real estate question yet. Would you rather be an office landlord during The Great Depression (1929-1941) or in today’s post-COVID, remote work era?

A recent poll showed 58% of respondents would rather be an office owner today, while 42% would have preferred 1929-41. That split says a lot about how brutal the current office market has become.

During the Great Depression, real estate values collapsed, businesses shut down, and vacancies soared. But there was one key difference—office space was still essential. The economy eventually recovered, and buildings retained long-term value.

Today’s market is different. Office demand isn’t just down—it’s structurally changing. Remote work and hybrid models have permanently altered tenant needs. Even in strong markets, lease terms are shorter, subleases are rising, and Class B and C properties are struggling to stay relevant. Some buildings have lost over 50% of their value since 2019, and distressed office assets are piling up across major cities.

During the Depression, landlords had to weather the storm—but they knew demand would return. Today, office landlords don’t have that certainty. The market may never fully rebound in its old form. The question isn’t just when office will recover—it’s whether some of these buildings will ever be viable again.

Which era would you take? Would you rather bet on a historical economic rebound or try to navigate an office sector that may never return to what it once was?

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Honestly, both eras are rough. In the ‘30s, you had deflation, bank failures, and no federal backstops. Now, you’ve got a structural shift in demand and capital markets that are scared of office. It’s not about which is “easier” it’s about which pain you’d rather manage: economic collapse vs. functional obsolescence. Neither is pretty.

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I’d take 1929–1941, not because it was easier, but because it was predictable in one key way:

Office was still essential infrastructure.

No one questioned whether people needed desks, phones, and a physical HQ. The collapse was cyclical, not structural.

Today? The fundamentals are shaken. The function of office is in question, and many Class B/C assets may become stranded. With that uncertainty, it’s hard to model a clear recovery timeline, or exit.