It's good to see your ideas.
Speaking of long bonds, they'll only have to drop a tad over 40 points and your "friend" will have a break-even trade.
If we can get cattle to break, oh say 'bout fifty dollars per cwt ... he might be close to a gentleman's loss. However, I've yet to run into a guinea negro that was a gentleman.
I'm thinking you've got decent shot at your ng timing ... cannot stay this close to zero forever.
If a decent rally does ensue .... your "friend" might get close to a small loss, considering the contango this market has carried the many years he's been saying "buy with both hands".
Laughing stock he is, but even a broken clock - set on military time - is right once a day.