"Mr Watson, do the Texans have a massage therapist?"
"Yes"
"Do you have to pay for it?
"No"
"Why then have you paid hundreds of times for something that you can get for free from your employer unless is was for something nefarious? How has someone who has lived somewhere for 1000 days paid for over 100 massages when it could be gotten for free at your place of work?"
It isn't that he paid for it a hundred times that is suspicious.
It is the fact that there are so many massage therapists he has seen.
In life, whenever you seek professional services (eg. doctor, lawyer, dentist, psychiatrist, financial advisor, hair-stylist, carpenter, and massage therapist), you usually don't hop from one to another so frequently.
You usually find one that is good and stick with them. That is how professional-client relationships work.
This is especially true for the rich and famous, who tend to have very high standards and are therefore less likely to visit a specialist that is unknown to them versus one that has proven to be good.
Rich and famous people tend to have a "go-to" person for each of their needs. They don't take "whatever and whoever is available" the way average folks do.
When you see the amount of different massage therapists he has seen, then it becomes a very big red-flag.
To me, it seems that Watson was viewing them more as "hook-ups" rather than "massage therapy sessions".