Are you assuming he deducts the entire loss amount from CG taxes? as in if he invests in (and loses) $100 on a portfolio, he can deducts $100 from his CG taxes - rather than a percentage of $100. Assuming tax rate is lower than 50% He loses more than he writes off in taxes, and so can cannot match his losses, only tax on the loss.
I'm not saying that he can save money by investing in a bunch of juiceros, just that each year when a few of his investments are duds he has a pool of unrealized gains that he can pull out tax free to match the losses.