These were 6x6 posts so yes there would be room for two bolts. Started out with 3/8x4 through a 3/8 log chain. Worked on a few but ended up getting 1/2x8 bolts and used the hook on the chain as a bolts wouldn’t fit through links. Most of the rest we were able to get far enough in to better wood that it worked ok. A couple we had to go into the side at an angle to find more solid wood. A couple we had to dig beside and push them out away from the concrete and wrap the chain around to pull out. Probably should have built a D-ring on a piece of flat with a couple holes for the bolts but as i said we got them all out in a couple hours so wasn’t too bad. We already had the building removed from the pad so weren’t constrained by that. If the building was still there probably would have been better to build the d-ring device. I was surprised that the poles didn’t come out when removing the tops as easy as some of them pulled. I guess they were more rotten than they appeared.