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Originally Posted by dcarson
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He does, but in 1995, he's somewhat too old for adventuring and in 2018, he's an invalid.
It's very plausible that Kessler actually owned a personal aircraft or two he bought in the 1960s and early 70s, unconnected to adventuring or the occult, which might have been upgraded as far as personal comfort goes as Kessler grew older and richer.
In the early to mid-60s, Kessler was a freewheeling buccaneer in petrochemicals and minerals, mostly based around Houston and Galveston, but with partners in France and various Francophone nations, as well as investments and business concerns in Africa, Asia and the Caribbean. At that time, Kessler had about an order of magnitude less available cash than the image he liked to project, so while he owned a series of yachts and started building a superyacht in 1965, he'd have looked for a cost-effective solution for private planes at that time.
By 1969, Kessler's actual financial resources had caught up to his image, but he was still only a multi-millionaire. He didn't reach his first billion until some point in the 80s.