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Not really, because the process is very gradual. You don’t sell all your stocks the day you retire, you gradually wind down until you hit some reasonably conservative allocation in your 80s or so like 30% stock/70% bonds. This certainly can put some downward pressure on the stock market if the rate of this winding down is higher than the rate that young people are adding to their 401ks but it’s counterbalanced by many other forces.

Annuity buy-backs, anyone?

Someone at Wall Street must have thought of that and pitched the securitisation already. Think about it - large companies agreeing up front to spend a minimum of X billion a year buying back their stock. And then WS banks parceling both sides of the risk and exposure to investors seeking anything with non-negligible yield.

Retirees generally only liquidate a portion of their funds. They start withdrawing something like 4% per year roughly half a decade ahead (to avoid withdrawing during a crash) of retirement. As others said they also shift away from risky investments.

slowly transition your assets away from growth stocks to bonds and dividend-issuing stocks as you age