&gt;There&#x27;s no new money &quot;injected&quot;. If he wants to buy a significant amount of stock, there will be some upward pressure on the price, because you have to find someone willing to sell, but that same condition applies to Apple. They have to buy on the open market just like Tim Cook. If a 100MM purchase is going to push up the market cap by 0.1%, it&#x27;ll do the same for both.<p>The injected money (or I will admit more accurately injected value) comes from increased demand.  The only effect of Tim Cook buying shares in increased demand for Apple stock.  Meanwhile Apple buying shares will be coupled with a decrease in value of the company&#x27;s assets.  Tim Cook&#x27;s purchase only provides upward pressure on the market cap.  The buyback provides downward pressure as well.<p>&gt;As for the buyback being important because it increases insider&#x27;s ownership, no, it doesn&#x27;t. At least not in any meaningful sense. There&#x27;s maybe 1% held by &quot;insiders&quot;. If Apple buys back 175 billion in stock at their current price&#x2F;value (a terrible assumption, but whatever), they&#x27;ll take 33% of the stock back. So the insiders will hold 2% instead if none of them sell.<p>Personally I would say doubling your ownership percentage is meaningful.  But like I said earlier the whole thing relies on the insiders having $150 billion in stock + cash which they almost assuredly don&#x27;t and likely can&#x27;t raise.  You keep on ignoring that condition.  I am arguing a hypothetical situation in which they do have that money.  You seem to be arguing that even the hypothetical is impossible because they don&#x27;t have that money.