I suggest you move past the debentures. 12% interest is predatory, mgmt got paid handsomely to hold shares, as did you and others. It's almost silly to try and leverage that as positive point for previous management engagement with available shares. 

So if what you are saying is true then why did it take 5 tranches over several months? 

The risk was there. It was a time when they had taken Taylor's GaAs platform as far as they could and need funding to help develop the Optical Interposer.