Deimos had plenty of money from somewhere, while he was in jail, and when he got out. He had people working for him, following Philip's activities, Victor's activities, keeping tabs on what was going on in Salem ......Deimos knows it all, every bit of it, and knew it before he came to town. He had plenty of money, and people working for him on the outside, while he was on the inside.
Yes, he plays it close to the vest....has only referred to having spent the past 30 years in prison, finally getting out, and giving the impression he came straight to Salem. First thing he did was come and tell Vic he owed him a job...knowing Vic would not do so.
Deimos had plenty of time to think and plan out what he was going to do when he got out.
After all, he knew exactly who to call to get the drug he wanted to poison Maggie, didn't he? Oh, he had his men everywhere, it seems.
But this thread is about Chloe........not Deimos. And I just do not think Chloe would have been involved with this much older man in any way.......not saying it might not be, just that I don't think so.