(CBS News) David Winoker was a guy who didn't take chances, always driving below the speed limit, always using several layers of sun block.
His wife says she urged him to go skydiving Friday, and he reluctantly agreed.
Taking that risk cost him his life.
The incident is shining a light on an industry that has almost no regulation.
Skydiving tops so many peoples' lists of things they just gotta try, despite the possibly deadly consequences.
When Winoker, a 49-year-old Manhattan real-estate executive, took the leap at a party celebrating a friends' 50th birthday, he assumed his life was in capable hands.
Harnessed in tandem to an instructor from Skydive the Ranch, a New York skydiving school, the husband and father of three jumped out of an airplane.
Witnesses told police there was a parachute malfunction.
Moments later, Winoker and 25-year-old instructor Alexander Chulsky hit the ground and were killed.
The United States Parachute Association says 3 million people skydive in this country every year.
In 2011, there were 21 related fatalities. Of those, just one was a tandem jump like Winoker's.
"Nobody will tell you skydiving is completely safe," concedes the association's Ed Scott.
The USPA acts as a non-governmental regulatory body in a mostly self-regulated industry.
The Federal Aviation Administration does, however, set guidelines for tandem jumps like Winoker's. Each such jump requires two parachutes and each instructor needs a minimum of three years experience and 500 jumps.
"The odds of both parachutes malfunctioning are just so small, they're incalculable. And it's something we just don't concern ourselves with," Scott says.
But experience and equipment are only part of the equation. The USPA says instructors must pass an FAA medical exam - the same exam private pilots undergo.
Winoker's funeral was on Father's Day - his father's 83rd birthday.
To see Jim Axelrod's report, click on the video in the player above.