I don't presume to be able to comment on the why and what for in this situation, as I don't have a personal referent, but I will say that in all the years I have known Matt, including the time he came out to visit my wife and I and stayed at our place for a few days, I never got the idea that he had low self esteem.
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“It takes considerable knowledge just to realize the extent of your own ignorance.” ― Thomas Sowell