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The judge who ruled on the case actually said specifically that it didn't matter whether he made the investors whole.

https://www.bizjournals.com/newyork/news/2018/02/26/shkreli-...

From article : Matsumoto rejected Brafman's argument that because investors made money with Shkreli, that he shouldn't be penalized for losses.

Matsumoto said in Monday’s order that under federal law, all of the money that investors put in Shkreli’s funds as a result of his fraud, about $6.4 million, must be considered a loss (h/t Reuters). The judge also said the Turing Pharmaceuticals founder should get no credit for paying investors back because he only did so after they became suspicious.