One thing is strange though, they're conceding bets on outcomes that are far from conclusive/decided. For example, the bet about the black hole & information paradox. There are many different ways both of them could be wrong/right. One such possible answer resides in string theory. A few string theorists put forth the idea that black holes may not have a singularity at all (thus, no paradox). Let me explain:
Massive enough stars collapse into neutron stars when they die. A neutron star is made out of neutron degenerate matter. Basically, when a star dies, gravity rips apart/compresses/implodes everything down to neutrons. The gravity is so strong that helium, hydrogen etc. cannot exist within the star, it immediately gets broken down into more fundamental components. It gets ripped apart and turned into this "neutron degenerate matter". This is because neutrons have enough energy or "strength" to resist gravity. This is why a neutron star is stable. But if a star has enough mass (more gravity), it's possible for even neutrons to break down and succumb to gravity. Some people have hypothesized that they can break down into quark stars but we have yet to see them. Instead, we currently believe they form singularities (a black hole) since there is nothing more fundamental to hold back the force of gravity.
Massive enough stars collapse into black holes/singularities because after neutrons/quarks, there is nothing more fundamental to break down into. But in string theory, there is. In string theory, strings are the fundamental component of the universe. A few (not all, it's pretty fringe/new) string theorists have hypothesized that a black hole could be simply a "fuzzball". It's basically a star made out of strings. It would behave and have the exact same properties that current black holes have (light cannot escape, no limit on size, extreme gravity, etc) but it resolves 2 of the paradoxes -- no singularity (no invoking infinity & breaking QM) and no information paradox.
See here: https://en.wikipedia.org/wiki/Fuzzball_%28string_theory%29
If string theory is correct, and fuzzballs are the true description of black holes, the bet itself is wrong. It would be like betting whether the sun was made out of cheese or wax. The answer would be neither.