After his contract with the Buccaneers ended after the 2016 season, he threw himself, as he had planned, into his restaurants, real estate ventures and philanthropy, including his Jackson in Action 83 Foundation, which provides emotional and educational support for children in military families. But like many players, he had a tough time adapting to a life without the brotherhood of the team.
“You can prepare to have another career and make money another way, but nothing ever matches that,” said Randy Grimes, who played nine pro seasons, all with the Buccaneers, left the N.F.L. with an addiction to painkillers and now helps former athletes with substance abuse issues at WhiteSands Treatment Center in the Tampa Bay area.
The pandemic, though, altered Jackson’s routines drastically. He fretted about having to lay off workers. Business meetings were virtual, diluting one of his favorite activities, networking. At home most of the day, there were fewer barriers to grabbing a drink.
The success of his former team, the Buccaneers, who won the Super Bowl the week before he died, was both a source of joy and remorse. The team’s championship had reminded him of the losing seasons he had endured with the team, Lindsey Jackson said.
When it became obvious to even his children that he did not have his drinking under control, she said, he moved into a hotel about 20 minutes away.