Another Las Vegas-to-Los Angeles prop bet is getting underway today. Once again, Dan Bilzerian is involved, but this time he’s on the other side of things. Bilzerian and renowned-investor-slash-notorious-prop-bettor Bill Perkins are putting up the cash for Brian Rast to attempt the same feat that Bilzerian pulled off just one month ago, namely traversing the 300 miles from Vegas to LA on a bicycle in under 48 hours.

If he succeeds, Rast will collect $600,000 from the two, while he’ll only need to cough up $100,000 of his own cash if he fails. As it turned out, Bilzerian had an easy time completing his attempt, finishing in around 32 hours, or about two-thirds of the time allotted. It might seem surprising, then, that Bilzerian would be willing to take the other side of the same bet and give 6-1 odds in the process. There are a couple of important differences, however.

Same feat, different circumstances

The most significant difference is that Bilzerian had plenty of time to train in preparation for taking on the challenge, and threw plenty of money at it as well, buying multiple high-end bikes, hiring Lance Armstrong as a coach, paying for a police escort out of Las Vegas, and so forth. Rast, on the other hand, has agreed to the bet on extremely short notice; he’s been training for a week, but the bet itself seems to have been agreed upon only yesterday, and Rast now has to begin his attempt today.

Another factor to consider in both bets is the terrain and weather conditions, as most of the route consists of traversing the Nevada desert. Obviously, as the year goes on and summer approaches, the weather gets hotter, and crossing the desert more difficult.

The real motivations

That said, I don’t think that the real motivations here have much to do with that actual difficulty of the feat, or with Perkins and Bilzerian thinking that the bet will be profitable for them in the long run. Both men have more money than they know what to do with, and tend to throw it around for attention and/or fun on a whim.

There’s probably more than whimsy going on here, though. Although Perkins happily paid up when Bilzerian completed his bet, he faced backlash from other people who’d put money on his side, due to his having allowed Bilzerian to draft behind his camera van for most of the trip. Ultimately, under mounting pressure, Perkins did ask Bilzerian to desist, and Bilzerian complied, but by that point he was only 100 miles outside of Los Angeles and well ahead of schedule.

Rast, for his part, was the guy who arbitrated during negotiations for the first bet. When controversy ensued in the aftermath, he came to Perkins and Bilzerian’s defense, pointing out how there was nothing in the terms of the bet which precluded Bilzerian from using a van in that way, and that Bilzerian completed the bet with so much time to spare it’s virtually impossible that it made a difference in any case. Of course, Rast had money of his own on the bet, and on Bilzerian’s side no less, so by his own admission he wasn’t capable of being truly impartial; his assurances, then, were probably worth little to those who’d bet on Bilzerian to fail, and subsequently felt cheated.

Based on that backstory, it seems likely that the motivation here is at least in part to dispel this residual controversy; if Rast can complete the same bet without drafting and with far less preparation, then all but the most delusional bettors will have to accept the fact that Bilzerian was always going to complete the challenge successfully, no matter what he did or didn’t do to help himself.

For Bilzerian in particular, as long as the final margin is narrow enough, he can spin the outcome into a PR win-win for himself, regardless of whether Rast actually succeeds or fails. Whatever the difference between their times is, you’ll have to chalk it up partly to Bilzerian’s training, and partly to the drafting. By playing up the former and playing down the latter, he’ll be able to boast about what great shape he got into for the challenge, while simultaneously arguing that Rast’s time shows that the drafting alone was not sufficient to change the outcome.

If you’re going to bet, go with Rast

I still believe that putting one’s own money on other people’s prop bets is a bad idea in general, both because it’s very likely that you don’t have quite as much information as the people involved, and because it sets oneself up for a variety of hustles. If you are going to bet, though, the smart money is usually on the person who is taking on the challenge; they’ll know their own physical limitations better than those laying the challenge, and most people will actually out-perform their own expectations when they’re extremely motivated, which is going to be the case when a lot of money is on the line.

In Rast’s case, I don’t think the lack of training is a huge deal, because it’s only been a few months since his MMA fight against Sorel Mizzi, so his conditioning should still be pretty good overall. Admittedly, Bilzerian was in good shape himself too before his attempt, but he seems like someone who concentrates on bulk (especially upper body bulk) rather than tone and cardio, whereas if we assume Rast was going about his fighting training the right way, his body is probably pretty efficient overall, and his legs and core are probably strong, since that’s where most of your power comes from in striking.

The desert heat also doesn’t look like it’ll be much of a factor, as cool weather and light rain are expected for today in Nevada, and tomorrow looks like it will be pleasant in the Los Angeles area. One major downside for Rast is that it looks like he’ll be biking into a stiff headwind most of the way. He can avoid the worst of that, however, if he rests in the afternoons when the wind is strongest, and does his hardest cycling at night and early in the morning when the air should be relatively still.’

All in all, I think Rast will put up a slower time than Bilzerian’s, but easily under the 48 hour target. I’m not going to be putting any money of my own on it, but I think especially at 6-1, he’s a slam dunk, and if I was going to set an over/under, I’d put it somewhere around 42 hours.

Is this going to be a trend?

Rast will now be the third poker-related person to attempt this particular bike ride. Samantha Abernathy did it first, but with a 72-hour deadline, having been offered a freeroll by Dan Bilzerian to effectively scout the route for him. Bilzerian was of course the second, and now we have Rast. At what point does something become a tradition?

I suspect we may see more prop bets involving Las Vegas, Los Angeles and bicycles in the coming year. Given how easily Bilzerian completed his bet and assuming Rast does likewise, we’ll probably see stiffer challenges in future. Summer in the desert will provide its own difficulties, of course, but we may also see shorter deadlines or additional conditions applied. Bilzerian and Perkins will likely get bored with this particular challenge and move on to other bets, but the data points they’re producing in the meantime may help set the lines for bets by other, sharper gamblers in future.

Alex Weldon (@benefactumgames) is a freelance writer, game designer and semipro poker player from Montreal, Quebec, Canada.