i think that maybe diamond was a criminal. like, literally the classic one that got away in noir stories, and she was playing him for intel, and thats how juno messed up as squad captain, and thats why she left him at the altar. its noteworthy than according to rita, diamond left before juno left the hcpd, which i think lends credence to the idea that she played him and bolted (maybe with hijikata?) and then he screwed up the case and left in disgrace. if thats the case, itll be interesting to see what their dynamic will be like. theres a lot of possibilities, all of which can push against different aspects of junos recovery. is she remorseful, and will he forgive her if she is? does she want him back, and will he take the validation if she does? itll also be really interesting to compare and contrast that with his relationship with nureyev, and puts his whole "this juno steel doesnt get distracted by a pretty face" thing in a new perspective.
i think theres a strong argument for it being puck, but i dont think theres that much bad blood between them. also, its noteworthy that puck is still a cop. its not impossible, or even unlikely, that hes involved somehow, but while i think he will make an appearance, i think diamond will be who hes looking for. i wouldnt be surprised though if part of the reason he and puck never really caught up is because juno got clean, (although the timeline is super fuzzy on exactly when he started having a problem and exactly when he lost touch with puck so take that with a grain of salt). a lot of people who youre friends with when youre not doing well are quick to leave you on the curb when youre getting better, especially with addicts ("you used to be so fun" is a common refrain) so i think that sort of dynamic would be really interesting, especially in the context of juno feeling like hes pushed everyone away. itd be encouraging to find that the people he ""pushed away"" dont care that much about his health.