> It also seems like leasing a 1.1M asset for 36k/year is poor retirement planning. 3.2% pre tax won’t ler you live that well.

Maybe he was betting on the price of taxi medallions to increase considerably.

> Putting a million into medallions because they’ve risen in value for 80 years is dumb.

It's the basis of investing in a lot of assets - like NYC real estate. Limit supply will protect your investment and it will always increase. This is also the basis of dollar cost averaging into an index. The assumption is that the markets/indices will always increase in value over the long term even if it may fluctuate up and down over the short term.

> These weren’t mostly owned by mom and pop individual owners.

Yep. Regulations and limit supply will do that. Just like most of the farm subsidies benefit the mega corporations, not the small farms.