Except as the company buys back each share the value of the remaining shares increases. If they buy back 500,000 shares at $25 per share, that costs the company $12.5M. Now the company has $37.5M in the bank, and there are .5M shares existing, which means the value of each share if there were no judgement pending would be $75 per share. With the pending 50-50 judgement that will either ruin the company or leave it intact, that means the expected value of each share is now $37.50, so you’d be an idiot to sell for $25. They couldn’t buy back every last share for $25, that’s just the cost for the first share, and that cost increases for each share they buy. If they somehow bought 999,999 shares for $25 each in one mega-transaction, the last share would be worth an expected value of $12,500,000. Would you sell that share for $25? And if the company executives tricked you into selling that last share for $25, they’ve defrauded you, and they go to jail. As each share is retired, the remaining shares measured against the expected future value of the company goes up, and therefore would require a higher and higher price to buy back.
And that doesn’t even touch what LonghornDave is talking about, fraudulent conveyance. If the company potentially faces a judgement of greater than the value of the company, and starts buying out shareholders in order to potentially leave the creditors with nothing, that’s fraud. It’s against the law.
Or to create another scenario, suppose that the company is facing that 50-50 coin flip a year from now. They have $50M in the bank. Why not just liquidate the company today, and pay off all the shareholders $50 per share? Instead of each shareholder getting a paltry $1, or $25 per share, they now get the full value of the company, and the potential creditors get nothing.
Buying back shares is equivalent to a partial liquidation of the company. One the one hand you could completely liquidate the company and get your full investment back. On the other hand, you could partially liquidate the company by buying back shares, trading company assets for stock. Why would the stockholders allow company executives to liquidate the company for less than the value (to them) of the company?
All of these potential schemes require the corporate executives to defraud the shareholders, because they require the corporate executives to buy the stock for less than the value of the stock. You might argue that stockholders can sell stocks any time to third parties for any price, and shareholders are frequently wrong about the value of the stock. That’s true. But the third party doesn’t have a fiduciary responsibility to the shareholders like the corporate executives do. If you sell your million dollar Picasso to the neighbor kid down the street for $1.00, that’s on you. But if you’re a financial trustee for a guy who owns that Picasso and you sell it to the neighbor kid for $1, you’re going to jail.
Edited to add: Or they could be defrauding the creditors, or a mix of both the shareholders and creditors.