It seems that Barry was a willing participant though, for whatever reason(s). ie I believe sometimes people/companies may invest in things that are known to lose money, which end up reducing taxes on more profitable enterprises. He may have figured it was more fun to lose money by participating in FDA's escapades than to pay it to CRA, for example. Seems the two were pals for whatever attributes each saw in the other, and also seems there may have been a fair bit of jealousy from others, including family member(s) because of it. jmo.
Barry evidently liked to invest in or partner with those who could be termed mavericks, or those wanting to shake up industries or change the status quo. After all, he built apotex by battling large pharma. He probably felt FDA, in spite of some faults, was such a person, trying to battle established companies or shaking up industries by starting new ventures and/or swimming against the established current so to speak.
It’s hard for most of us to imagine, but the millions of dollars that Barry put at risk with FDA and others wasn’t material to Barry, given his overall wealth.