Accept challenge. Attempt to hire the alchemist to make various battle poisons, sleep toxins, aerosols and the like for my champion (keep the discussion focused on the legal aspect, but allow hints of other opportunities as well.
"So, is there any way you can assist my gladiator in the arena this week?"
"Hm... What's your school's name?" The Tenderfoot looked down at a large stack of papers.
"Pretty's Finishing School."
"Hm..." The Tenderfoot spent several moments leafing through the papers before saying "No."
You're somewhat surprised by the outright statement "Why not?"
"Because, you're not on the list. See? Win a few fights, get put on the list, then I'll be happy to help you. Hell, win a few more fights I'd be willing to join your school. Been wanting to get into the business myself all things considered."
"So... You wouldn't help me if I offered you a position right now?"
"No." The Tenderfoot shook his head "If I gave you a potion right now, the officials would wonder where it came from? Potions are easier to track than I'd like with those damn diviners around." The Tenderfoot made an odd noise between a retch and a cough "Plus I don't think you want me around. I'm no good in a direct fight. But... Put me onto your team when you have some burly chaps who can hit hard around and I'll make sure they hit even harder or your money back guaranteed."
"Hm..." It would be nice to have an alchemist on your team... Well a tenderfoot, you get the idea that he's not quite alchemist material yet but... You'd have to consider it for whenever you get around to winning a few fights. "Maybe. What can you make anyways?"
"Oh this and that. Defensive Potions, health potions, a few life potions, Firebrand Potions are a personal favorite of mine to make. I've also got some things that are a little less than approved of. If you know what I mean."
"Poisons?" How convenient, you were just about to bring that up.
"What? No no no no. That'd be illegal you know? But, sometimes these potions have awful side effects. I mean, IF one of your gladiators happened to drop some of it on their weapon and IF the opponent happened to posses no immunity to such a thing and IF the opponent started to feel sick well... We can't stop fate can we?"
"Of course not."
"I mean, who are we to meddle in the affairs of those human gods of yours? Heheheh."
"Well, since I can't buy from you I suppose our business is concluded for now?"
"I'm afraid so. But getting on these lists are more of a formality than anything else. A fight or two at most and I'll be handing you whatever you need."
You left the Tenderfoot's shop with a small smile on your face. While you may not have gotten what you wanted right away you knew how to play the long con. Things would be looking up for you in no time.