Update:
Multi-eventer ran today in a large city half-marathon. Weather conditions were quite good. He ran 1:31.high .
This time he didn't take a break and presumably gave a solid effort. However, I watched the last 500m and to be honest it looked like he wasn't as fatigued as he should be at the end of a race. Still I'm confident since winning the bet would require running nearly 2 minutes faster back-to-back and seems to be out of reach at the moment. Remember, he has until end of 2019.
Some stats:
Weight today: 183lb. I believe he was down to mid 170s at some point in the summer, but then drank too much.
Mileage: Fairly consistently around 100K/wk
Plot-twist
Here's the most exciting update. During lunch afterwards we were talking about our chances for the bet and we each seemed confident. So we added more to the stakes. He will attempt his first marathon in a low-key race (very few sub 3hr runners) this coming spring. If he runs sub 3, I will pay him an additional $1000. If he runs and is slower than 3hrs, he pays me $100. If he does not run for any reason, he pays me $50.
So Letsrun... am I still safe?