heh, sure, I'd say that in the whole scheme of things, that looked like pretty good market timing.
It looks like the Friday before your Monday sale was when
TARP was announced. That led to a 2-day bump in the S&P500 of nearly 9%. I'd guess your brother saw that as a high point amidst chaos, and correctly guessed that the chaos was not yet at an end.
Your buy-in in January was less perfect, since you also managed to find a high point (which is the opposite of what you want!) Literally any other day in the two months previous or the six months after, you would have bought back in at a lower price than you did. In other words, you had a 1-in-240 chance of hitting that crap-jackpot, and you did!
Getting lucky like your brother did, particularly early in an investing career, is actually horribly unlucky in my opinion. Because that experience is then often assumed to be the result of skill, and it can take decades of getting beaten up for that person to be convinced that the market is a nasty bitch, while the person who was on the other side of that trade learned it much more quickly.