He’d have to operate in something other than weapons, just because it would be too predictable a route. Not to mention, a huge portion of sales between the Sons and others have to do with the sales pitch. Duke would have to know about these things in order to give that. He’s charismatic, and he knows his way around a gun, so he could at least bullshit it, but it’s not exactly something the Sons would trust. There’s also the option of telling him what he’s hauling and trust him, but not knowing is what gives him a loophole in the way of legality.
Assuming he decides knowing is worth it, there’s still a question of how well he would work with the Sons. Jax, he could handle. They kind of see eye to eye. They have the same moral compass, more or less. Duke knows when to let someone like Jax think they have the upper hand. The problem is, it’s more likely he’d be dealing with Clay. And to deal with someone like Clay, you have to either be desperate or just as much of an asshole. Duke is neither. He might pull off a few jobs, but Clay would be adamant about having him there on a certain day, at a certain time, “wearing that pretty little number I got you”. Alright, the last part was more hyperbolic, but that’s the amount of leeway he would be given. And that’s no bueno.
The typical stretch would be to have him as a patchmember, meaning he’s gone through prospecting. Prospecting normally lasts a year, but there have been cases of men who patch in before the one year mark. On the other end of the spectrum, there are guys who are prospecting for years and never make it through. The rules of prospecting include “speak when spoken to”, “I say jump”, etc. Again, no freedom. And no patience. The probability of him working with the Sons or being a Son is so low, either is almost impossible.
Most likely, he just knows one of the Sons. Probably met Juice way back when. Maybe he knows Rat. Maybe his dad was buddies with JT. I’m thinking personal relationship is the best way to go.