At what point do you gamble on Bonds in a salary-cap draft?

[duckbillgates]

Our league bases salaries on the Sporting News guide's auction draft prices. Since it comes out in December, Bonds costs $35.
But if there comes a point where I'm putting my team together and feel I have some room under the cap, how soon should I pull the trigger in hopes of getting a half-season or more out of Barry?
I'm thinking that once I have my starting lineup set, if I have the money, I'll probably go for it, assuming somebody doesn't go ahead and gamble on him earlier.
I seriously wonder whether he'll get drafted at all.