I highly doubt it for a number of factors.
- Most of his dives look to be rec depth
- He isn't running any crazy gear like a CCR
- He has instant access to a chamber, so any DCS worries are virtually zero
- There is no go-itis for him. If weather is bad, he just packs up and sails to somewhere nicer
Out of all the rich people hobbies, scuba is about the safest
Scuba diving is a pretty risky activity on the scale of things that rich people do in their everyday life. Golf and cycling are a lot safer.
Scuba fatalities fall into a few buckets, the big two are inexperience/bad decision making, and older folks with health issues (underwater heart attacks/respiratory distress, basically).
As a former dive pro, an overweight 63 year old is someone that I would keep a very close eye on while diving.
The odds are pretty low, but there is a reason that many life insurance companies exclude scuba divers from their coverage.
That said, I'm happy to let him live as dangerously as he wants, he deserves it.