This trade was never a losing trade the way I followed. It was two wins in a row.
He bought shares and price increased. Avg cost was low 24x? Then at ~$250 he closed his long.
He closed it by converting to a delta neutral short vol position instead of selling the shares. When he gained on short vol he was able to leg into wings that capped his risk from short vol @ 250 at a better price. Probably held while he still felt he had something to gain on short vega/gamma with bounded risk and then finally took everything off.
This sounds more accurate.