For reasons that will become clear when you read my interview with Gil, he keeps his true identity and specific whereabouts a secret.
During our conversation, he admitted that he was calling from somewhere in Florida but that is all he was willing to divulge.
TME: Give me a little background on your history with death pools. How did it start for you?
Gil: I think a lot of the dead pools stem from that Clint Eastwood movie from the 80s (“The Dead Pool”). That movie was about someone who actually went out and killed celebrities in order to win their pool. By the way, that’s the number one thing you are not allowed to do. If you kill them, you don’t get the points.
TME: How long have you been doing this? And is it something that anyone could take part in?
Gil: I’ve been doing this for about 20 years and I run it kind of like a fantasy football league. I do my research during the year. I keep track and I’m vigilant about it. Still, I only came in third place last year, so maybe I’m not as good as I used to be.
The pool I’m part of is not public. It’s just a group of people who have been doing this for years. There are public pools out there and you go through their portal and pay an entry fee and you can become part of a huge league. I don’t advocate for any of those but a quick Google search will take you there if that’s what you want to do.
TME: Which celebrity deaths last year really shook things up in your death pool?
Gil: Nobody had David Bowie, George Michael or Carrie Fisher. Those sort of came from nowhere. The big-point people last year included Joey Feek (female country music artist), Rob Ford (former Toronto mayor) and (reality TV star) Big Ang.
TME: I’m guessing nobody had Prince in their pool. That was a shocker.
Gil: It was. When Michael Jackson died, there were people who had him in their pool because he had done some pretty crazy stuff. The baby-dangling incident and all of that. Nobody saw Prince coming.
TME: I’m curious about your methodology and could you share a few names of celebrities whom you think will be checking out this year?
Gil: I have a big category I call “The Year of the 90s,” meaning celebrities who are in their 90s. There are so many that if you don’t pick them, you’ll be on the defensive because so many people have them. On that list are people like Kirk Douglas, Betty White, Jerry Lewis, Mel Brooks and - at the top – Queen Elizabeth and George H.W. Bush. He used to be like Superman, jumping out of airplanes on his birthday. He’s not doing so well now. If you don’t have some of those names, you’re going to regret it when everybody in your league cashes in.
TME: So we’re talking money here. How much money have you won in past death pools?
Gil: Uh, as long as the IRS isn’t listening in, I can’t put an exact dollar figure on it but over the years, I’ve won the pool outright many times and have finished in the money on several occasions. As they say in horse racing, it’s better to walk to the window than not walk at all, so even third place is not so bad.
TME: Any longshots on your list?
Gil: Yes - and it’s always good to have a name that nobody else has. This year, my long-shot pick is Johnny Manziel (troubled 24-year old former Cleveland Browns quarterback). I would compare him with people from the past like Amy Winehouse or Rob Ford. This guy is out of control.