I feel like Clyde didn't want to ask but with Cole being a Bonebreaker guild member he probably felt Cole was... better? at what he did? Like Clyde probably thought Cole would have proper swindled the fancy bits or bribed the guild auditors or something.
I feel like Clyde ultimately felt Cole was better than he was... and if Clyde started to be like "Where/how did you get this!?" and Cole was just like "Trust me and don't worry about it"... and Clyde did trust Cole and didn't worry about it... then Clyde's right to be pissed because Cole basically lied when he told Clyde it was handled properly.