If you note the volume indicators are not adjusted (the prices are) to the RS so divide by 500 for the ones prior to Feb 25th.

The 312,571 of Now 30th is only 625 shares.  He did make money there if he bought back the following month.
The May 14th one may have made a little bit of money if he bought back before May 27th.. (0.95 to 0.90) but not more than that, and if he still has them he has lost substantially..  (0.95 to 1.35).
I'm really surprised that there is ANY shorting of a stock like this.  Whoever is doing it must have the cash to cover any loss as I doubt a broker would cover it.