My (M34) wife (F34) became best friends with an old flame. How to navigate?

My wife grew up in a small town. There was this one guy who we’ve called Adam (not his real name) who was a troublemaker. He was friends with them as kids. In high school, he got expelled for telling teachers to fuck off. He had no relationship with his parents and he was an angry teen. He and our other friends had physical fights, but never anything crazy. My wife was never that interested in him, but there was an incident where they once had sex in the back of a car while wasted on the last night of senior week. <br><br>He was a shit dude. She realized the next morning it had been a mistake. However, I never was a physical fighter, so the fact that she was with Adam after school made me look like a chump. It was a shitshow of rumors and drama. It ended up being so embarrassing that my wife, our friends and I just kept a low profile, did our time and got out as soon as we could.<br><br>My wife and I went to college, came back and met up again as adults, got married and have 2 kids. I really loved her. Meanwhile Adam went to a few colleges, dropped out, joined a few bands, did a few years of hard drugs and had a few memorable meltdowns. He looked like a 40 year old at age 27. But in his late 20s, he apparently got his shit together. He went to rehab. He went back to school and started working as an electrician. That was 5 years ago.<br><br>We moved to the city 3 years ago and stopped seeing him, but I would hear he was doing pretty well as a young single guy in the city. He looked better and told people he was sober. My wife and her friends mostly talked about how much they wanted nothing to do with him. <br><br>Anyway - when COVID happened, we moved in with my wife’s parents in their old house. So we’re back in this small town again. At first she was dismissive of Adam, but the other day I came home from a grocery run and my wife was hanging out with the old crew, laughing, having a great time, and there he was. He looked like a completely different person. Clear eyes, a clean shave and nothing else to do. It was a little awkward, but he was polite to me. We chatted a bit and he was respectful.<br><br>Anyway, since then, Adam has been over every day and they’ve been inseparable. We live in her parent’s old house, and they’ve been hanging out in the backyard every day, as a group. Adam has been doing a lot of the work on my wife’s house, doing all the electrical work and house wiring for her, which I guess is a conflict of interest, but I’m not going to pretend I’m some kind of electrician, and he does good work. He’s also been doing a lot of work for me and my business as well. It’s been an unexpected windfall, but I’m not really sure if it’s a good idea for my wife to be so close with him. She’s been going out to lunch with him as well when it’s just the two of them, and I’ve noticed that yesterday when we were hanging out yesterday the two of them were a little quieter, and today she told me that they have been talking about our marriage. I don’t know what to say - he’s been nothing but nice to me personally, but I’m starting to feel like he’s manipulating her. I’m not sure how to navigate this - I don’t want to tell her who she can and can’t be friends with, but at the same time I don’t know that I’m comfortable with her talking about our marriage and personal business with him. <br><br>The other issue is that yesterday the two of them were hanging out at the house, and I walked in on them drinking - it was only beer, but they were both tipsy, and Adam was telling her stories about his sobriety. When he saw me he was embarrassed, but he said it was just one beer and he was fine with it. My biggest problem is that my wife has a tendency to enable others - her sister is a drug addict, and as a result of that my wife lets a lot of people walk all over her. I’ve been working on her to set better boundaries, but now I feel like she’s allowing Adam to walk all over her as well, and I’m not sure how to say anything. Any thoughts?