No one can truely know what happened under water - that is always the challenge.
However, if the anchor hit the log before it began to dig in, no anchor could set. It would feel set, because the log was settled in the mud a bit. Even backing down under power would feel good. But at some strain more than your engine could bring to bear, it would move.
Dumb luck. But it is one reason I often set 2 anchors (yes, there are some negatives there too) when I expect some violent wind... which is often in the summer. I once had EXACTLY the same experience you had with a small tire. However, I had set 2 anchors ~ 100 degrees apart, and the second did fine.
Don't blame the anchor. Do realize that Chesapeake City has lame holding ground.
(when asked how he reached the starting holds on a difficult rock climbing problem that clearly favored taller climbers - he was perhaps 5'5")
"Well, I just climb up to them."
by Joe Brown, English rock climber
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