The hole was ready and and the hope was that the butt end of the log would slide down the corner and drop into the hole.

Lines were tied to each side to prevent it from swinging as it was pulled up.
We got it all rigged up and tried lifting it with optimistic anticipation. First try, the winch did its best, but was just not strong enough. Not only was the log just too heavy, but the angle was not right and there was too much friction on the top of the wall. Many forces against it...
So, Jeff lifted while I put boards under so we could get it started as high as possible. We also dug a trench under the butt end to improve the angle as much as possible.
Closer and closer it got, but not enough to allow it to lift up. We then tried using a come-along to pull it up, but still not doing the trick. It was essentially just wedging into the corner but not lifting up. Jeff decided the next step was to cut some of the end off the pole. He'd wanted it to be a little longer than necessary just in case, but turns out we could really do without 5 feet. This would help considerably.
Finally, thanks to the help of some very generous neighbors over the weekend, two logs were raised. They used the same method Jeff and I had tried, but used the come-along and the tree instead of the winch. They also had three strong guys instead of me. It took about 6 hours of work, including a few rainstorms, but they persevered. I arrived to see two vertical logs in the front two corners, very exciting progress.

The next two are in place and ready to lift.

While these back two poles have narrow holes to drop into there are trees behind that we can use to lift higher. We'll see...
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