Not a fair contest wrote:
You did well to stack the odds so much in your favour. If you were doing this on 5 min miles you'd obviously do it as reps and would double even if one of them was extremely short. Even triple. But no reps, no doubles, and only 400m warmup(!) gives him no chance. If he wins (and not because you blow up) it'll be because he has much more talent. You should easily win this after a ton of volume at 9:50 plus some hills, drills, weights, (plyos?), and running into a headwind as often as you can. And wearing a weighted vest. There's no way you can lose this.
Funny enough, I had to very little to do any stacking. Like I said in my original post, the no reps and no doubles came from our teammate who posed the hypothetical to begin with - I initially sided with 5:00/mi until that became part of the hypothetical. If reps and doubles were allowed? 5:00/mi wins out I think, and I wouldn't have taken the bet to begin with.