A witness told TMZ, who obtained the video, that Halladay was "dramatically increasing and decreasing in elevation" over the Gult of Mexico.
"He was flying like that all week," another witness told the publisher. "Aggressively."
Halladay, who was 40, had owned the ICON A5 plane for less than a month before Tuesday's crash, and he was among the first to fly the aircraft.
Just weeks before the Cy Young Award winner's death, ICON Aircraft CEO Kirk Hawkins announced new guidelines for low-altitude flying.
"There is little formal training required by the (Federal Aviation Administration) or provided by traditional transportation-focused aviation training programs to adequately prepare you for low altitude flying," Hawkins said in an email to customers on Oct. 17. "Given this, our goal is to take a proactive, leadership role in the flight training process and we have developed our own low altitude guidelines from lessons learned over decades of military, seaplane, and bush flying."
The ICON guidelines said flying the plane 300 feet above water or undeveloped ground "provides a reasonable margin for a pilot to make decisions and maneuver the aircraft away from terrain or stationary hazards."
Halladay had tweeted that flying the ICON A5 felt "like flying a fighter jet."
The FAA is investigating the crash, although early evidence suggests that low flying over water was an element in the cause of the crash.
Federal investigators determined that low flying was part of the problem when the man who led the plane's design, 55-year-old Jon Murray Karkow, died while flying an A5 over California's Lake Berryessa on May 8. The National Transportation Safety Board (NTSB) blamed the crash on pilot error, saying Karkow mistakenly entered a canyon while flying too low, causing the plane to strike the canyon wall.0comments
The FAA recommends flying at least 1,000 feet above congested areas and 500 above open people or structures on the ground or water, other than while taking off or landing, USA Today reports.
The former Blue Jays and Phillies pitcher's plane went down around noon off the coast of Florida, Pasco County Sheriff Chris Nocco told reporters at a news conference. Halladay was the lone known occupant, and three mayday calls were made to air traffic control.