Vincent Jackson’s friends haunted by questions about his unexpected death

As they await an official cause of death, friends of former Bucs star Vincent Jackson are struggling with more questions than answers.

About how he ended up at an extended-stay hotel.

Why he didn’t reach out to them.

And what kind of pain he was in.

For Adam Itzkowitz, who co-owned Cask Social Kitchen in Tampa with Jackson, it’s all a mystery.

He’s haunted by so much sorrow imagining Jackson at that Brandon Homewood Suites, day in and day out, not responding to attempts to reach him. All alone.

“It’s hard for me to think about it because of that. That solitude at the end,” he said. “And mentally, you almost need that closure, because you look around and think, was there anything that I could’ve done to stop that?”

How could the 6-foot-5, 230-pound Jackson, so visible in his post-career life as a businessman and philanthropist, vanish in plain view?

Building a legacy

Jackson was meticulously prepared for his football afterlife. After an NFL career that spanned 12 seasons, the three-time Pro Bowl receiver charged into retirement from the league with multiple business interests.

His parents, Terence and Sherry, each served in the U.S. Army, and Jackson demonstrated his passion for philanthropy with his Jackson in Action 83 Foundation that focused on military families.

He started his primary business venture, CTV Capital, while he was still playing in 2012. A real estate and development company, it offers construction, property management and insurance.

Jackson told business partner Mario Frias that he could have continued his career after his five-year, $55.5 million contract with the Bucs expired following the 2016 season. But unlike many players, he decided to walk away while he still could, rather than limp away from a sport that can be unforgiving to the human body.

“He said, ‘I’ve got plenty of money. But the most important thing is, I like waking up and playing with my kids,’” said Frias, who had recently been working with Jackson on the renovation of the landmark Manhattan Casino in St. Petersburg. “If I take more beatings, I’m not going to be able to do that.”

Jackson and his wife, Lindsey have four children. She is a first-grade teacher at Berkeley Preparatory School in Tampa.

But the couple, married since 2011, had been separated for months.

Itzkowitz, who got his law degree at Stetson in Gulfport, met Jackson through a mutual friend a few years before he stopped playing for the Bucs.

Though the two also invested in Dockside at Riviera Dunes, a waterfront restaurant in Palmetto, Cask Social Kitchen was “always his baby,” Itzkowitz said.

The motto is Eat. Drink. Be Social.

Although his name or likeness appears nowhere, Jackson’s fingerprints are on every facet of the restaurant. It includes the menu, described as “American fare with a Southern twist.”

“He obviously was the financial piece of the build-out, but he was the brains. He gave me the vision for what he wanted executed from there,” Itzkowitz said.

Jackson was deeply engaged, from tasting dishes before they left the kitchen to interviewing restaurant managers, Itzkowitz said.

But Jackson didn’t want Cask to be known as Vincent Jackson’s restaurant. It would have to survive on its own merit. Consequently, other than a framed American flag that flew over Bragam Airfield in Afghanistan dedicated to Jackson, you wouldn’t find any mention of its famous owner there.

The confounding thing to his business partners is that Jackson was always an eternal optimist. If the restaurant had a bad week? Tweak the menu. If they had a bad quarter? We’ll get them next month.

Football analogies were often referenced. “We’re right at the goal line,” Jackson would say. “We’ve just got to brush ourselves off.”

In fact, when an employee at Cask Social Kitchen came into contact with someone who may have had the coronavirus, Jackson shut it down as a precaution — at enormous cost and against the advice of Itzkowitz. Jackson believed it was the right thing to do.

When they opened the restaurant, Itzkowitz insisted on having one of Jackson’s popular sayings anonymously engraved on a beam beneath the loft: “Onwards & Upwards.”

Jackson even mentored some of the Bucs’ young players, such as former quarterback Jameis Winston, about managing life after football.

The first time Frias met Jackson at a coffee shop to discuss possible business opportunities, he was impressed by Jackson’s humility.

“You see this guy, he’s a football player, but you look at him and he looks like a movie star,” Frias said.

“He said, ‘I don’t know what we’re going to do, but we’re going to become partners. I worked hard my whole life, and now I’m at the point where you get to build legacy.’ And this man was a living legacy.”

Frias said he was on a Zoom call with Jackson the Thursday before he died to discuss efforts to reopen the casino hall in south St. Petersburg in two weeks. Jackson was still fully invested in his business dealings, making his death even more of a shock.

“One of the things that hurt the most was to find out that he was suffering, for whatever reason, and never reached out to any of us,” he said. “None of us. We all were sort of amazed. I would’ve brought his ass right home. I’d do anything.”

Did alcohol play a role?

By any measure, Jackson’s athletic and academic achievements are remarkable.

He was a straight-A student in high school who majored in business at Northern Colorado. A two-sport star for the Bears, he set the school’s receiving records and led the basketball team in scoring for two years.

Drafted by the Chargers in the second round in 2005, he overcame an injury-filled rookie year to become their go-to receiver. Twice he was named to the Pro Bowl in San Diego — in 2009 and 2011. He reached the NFL’s all-star game again in 2012, his first season with the Bucs when he had a career-high 1,384 yards and eight touchdowns. He led the NFL with 19.2 yards per catch.

But there were signs of his alcohol abuse before he arrived in Tampa Bay. Jackson was arrested and charged with driving under the influence twice, in 2006 and 2009, while playing with the Chargers. He pleaded guilty in both cases and was fined $2,408 and ordered to do a total of 15 days of public service. Because of the DUI arrests, Jackson was suspended for three games to start the 2010 season for violating the NFL’s personal conduct policy.

Those problems seemed behind him once he arrived in Tampa Bay.

But family members told investigators they had “reason to believe (Jackson) may have suffered from chronic alcoholism and concussions,” according to a statement the Hillsborough County Sheriff’s Office made after Jackson’s death.

“Honestly, I’m looking back on it myself, and I missed it,” Itzkowitz said. “And I was around him a lot. But that said, any social interaction I was with him at, it wasn’t unusual for someone to have a drink.”

The social drinking didn’t raise eyebrows, his business partner said.

“It wasn’t like he needed to have a drink in his hand,” Itzkowitz said. “It wasn’t like that at all. I’ve met with plenty of people and it’s 10 o’clock in the morning, and they’re pouring themselves a beer. That wasn’t it.”

But the Jackson family was certainly concerned when they didn’t hear from him for a couple of weeks. They called some of his business associates, including Itzkowitz.

Itzkowitz tried to call and text Jackson. He heard nothing back.

“That’s when I started to get a little nervous about things,” said Itzkowitz.

Responding to a missing person’s report filed by Jackson’s family, the Hillsborough County Sheriff’s Office finally located the former Bucs and Chargers receiver at a Homewood Suites at the end of a cluster of hotels on South Falkenburg Road on Feb 11.

“I’m curious as to what the sheriff’s office did or didn’t see that ultimately led them to just say, ‘Okay, everything is fine here,’” Itzkowitz said. “I get there’s not much they can do, I’m just curious as to what it is. Because in my mind, I’m thinking at that point, he was not in the right state of mind.”

Jackson’s family, which has limited its comments to brief statements made through a family spokesperson, must have believed that, as well.

After locating Jackson, according to a sheriff’s office source, the family sought to file a petition under the Marchman Act. The Florida statute provides for emergency assistance and temporary detention to individuals requiring substance abuse evaluation and treatment.

“It’s for people who are in danger or harming themselves or others because of their substance abuse,” said Robin Piper, a mental health counselor and CEO of Turning Point in Tampa. “Because they can’t stop drinking or using drugs.”

According to a preliminary case summary report by the sheriff’s office, there were no medications found in Jackson’s room, but a sheriff’s office source said numerous liquor bottles were discovered.

Before the sheriff’s office was notified about the Marchman Act, however, it was too late.

Allison Gorrell, executive director of Jackson’s foundation and a family spokeswoman, would not confirm that the family sought to use the emergency powers of the Marchman Act to intervene. Such requests are exempt from public records laws.

A profound loss

The cause of Jackson’s death has yet to be determined, and the process could take several more weeks, according to Hillsborough County Medical Examiner’s Office spokesperson Michelle VanDyke.

Jackson’s family donated his brain to researchers at Boston University to determine if he had chronic traumatic encephalopathy, a degenerative brain disease linked to repeated head trauma.

It was around the end of January, just as Jackson’s former team was preparing for Super Bowl 55 in Tampa, that “he kind of went off the grid,” Itzkowitz said. “I’m guessing at that point is where he started to deteriorate,” he said.

While Jackson had many varied interests and businesses, there wasn’t a lot of interaction between them. He was able to compartmentalize his private life and numerous projects.

Itzkowitz said he received a call from someone close to the family Feb. 15 informing him of Jackson’s death.

“I want to say I spoke to (Jackson) when the Bucs got to the Super Bowl, maybe championship week,” Itzkowitz said. “I had asked him if he was going, and he said, “They’re charging $10,000 a ticket. I’ll watch it on TV.”

While Frias spoke with Jackson the day the sheriff had checked up on him, he said he detected no signs his friend was in trouble.

“I was always used to Vincent disappearing for a couple or three days,” Frias said, noting Jackson’s busy schedule. “It would take him three days to get a call back to you.”

This week, Frias and his friends were thinking of a way to honor Jackson.

“We’ve opened a food hall, and we’ve decided to keep one of the kitchens for ourselves,’' Frias said. “We’re going to call it VJ’s. It’s going to be a new American cuisine. I couldn’t think of a better way to memorialize him at a place he gave everything to.’'

To Frias, Jackson will always be that guy wanting to help others wherever he could. And the circumstances of his death will not eclipse the enormous generosity of his life.

“If I live another 100 years, I will never forget his face,’' Frias said. “It just pops up. That smile, that sheepish grin that he had. He was an amazing guy. I’ve known him a handful of years, but he left a mark on people.

“The world is a better place that he lived here. But it’s definitely a sadder place that he’s gone.”

Times staff writer Joey Knight contributed to this report.