Alternatively, [ Tim ] might think Bitcoin is well worth above $375, but knows that he a chance to gather a much bigger position if he doesn't buy it on-exchange, because off-exchange prices seem to (largely) follow the on-exchange price as "the market price", while there is no public price finding mechanism for off-exchange transactions (excluding localbitcoin).
But if he thought that bitcoin was worth 390$, and bid for 390$, why would he not
also buy on the exchanges, after the bids closed, until the price rose to 390$?
Suppose that, as you suggest, he refrained from buying those 375$ coins at the exchanges because he wanted bitcoin to remain underpriced and thus discourage other bidders. If that is what he thought, he should have bid at some price between 375$ and 390$, probably closer to the latter. But them after the auction closed, why didn't he rush to buy those underpriced coins? If he thought that buying 2000 BTC at 390$ was a good deal, why would he not buy 1000 more at 375$?
Perhaps he was not a rational player, or was lazy, or became more pessimistic betwen 12-04 and 12-05, or had some other reasons; but what about all the other whales, including those who did not enter the auction? On 12-05, obviously none of them thought that BTC was worth more than 376$.
So, Tim
may have bid for more than 375$. But it is also quite possible that all the bidders (including Tim) acted rationally, and all of them bid below 375$.
Poll
