DeSean Jackson was nine when his father, Bill Jackson, along with a four-man squad, began his training for his future athletic career. Grew up playing both football and baseball, but the love for that one sport grew manifold. It was the 2005 MLB draft, with Jackson already emerging as a first-round pick. Ahead of the draft, he had an individual workout with the Tampa Bay Devil Rays. Jackson’s father and coach, Bill, was beaming. The prep was on for the interview, which would finally kick off his professional career. “I’m prepared to give up football,” Jackson was pressed to say these words. A seven-figure amount was at stake, but Bill was crestfallen at what happened next.

The gridiron demands passion. It’s not a cake walk to enter the pro league. But Jackson could not give up the rugged sport. He walked into his interview and was asked about the very question. Would he give up football for baseball? “Nah, I can’t give up football,” he said.

Travis Clark, who coached Jackson and has been a long-time mentor, later said that he (Jackson) had grabbed the baseball bats and swung them outside the room. “I just didn’t really have the love for baseball like I have for football,” Jackson says now. “It was kind of hard to fake the funk.” It was an emotional rollercoaster that the Jackson family went through, and after 20 years, DeSean let it out.

His confidence in his winning culture stems from overcoming his skeptics. “It’s been the same challenge that I’ve had my whole life,” Jackson narrated the emotional episode to the Athletic. “I’ve always been doubted. Who I am and how I was raised, you could put me in the ring with anybody, man, I’m going to come out on top.”

After rejecting the MLB Draft, he made it big in the world of football. He entered the 2008 NFL Draft, picked up by the Philadelphia Eagles. Winning the Super Bowl along with three Pro Bowls, he made his own destiny. His father saw his rise through the ranks, but unfortunately, he couldn’t see him wear the coveted ring. Bill passed away in 2009 after battling pancreatic cancer.

Now, after retiring from his NFL career, he is back to collegiate football, pouring his energy back into the students. “I want to be in a situation where you look up and, man, DeSean Jackson was a hell of a player, and he transitioned into being a hell of a coach,” Jackson said. “Anything I put my name on or attach my name to, my mindset is just to be successful.”

Even after achieving success in the Pro League, DeSean Jackson is bittersweet about his Super Bowl ring/

A Super Bowl ring won with a bittersweet feeling

“He changed the game; He really was the first true 160-pound receiver — a super threat,” DeSean Jackson’s former teammate Darius Slay said of him. After wrapping up his prolific career, earning Pro Bowl honors at two positions, kick returner and wide receiver, Jackson does not wear his Super Bowl ring.

“It’s a bittersweet situation,” DeSean Jackson put across in a conversation with LA Legends. “I feel like no. My brother be trying to get me to wear it… I’m saying like I was a part of the process. I went, you know, all season, workouts, training camp.”

DeShaun did not play in the Rams’ Super Bowl showdown against the Bengals. After wrapping up a decent season with the Rams, with 221 yards and eight receptions, he bid farewell and went to the Raiders. Jackson continued. “Should we beat the defending champions the year before, which was the Tampa Bay Buccaneers, in the game I played, and I went crazy on them, so I made a big play, a 75-yard touchdown that game, and helped win that game.” But he contributed immensely to the Rams’ 2021 season.

He went on. “But I don’t know what it’s really like, and I feel like this too, like, and then my career goes to defining a ring.”In the NFL, there’s no tough rule to bestow a Super Bowl ring on a player who has departed mid-season or so. The league is pretty generous in that aspect. But having the ring doesn’t mean much for DeSean when he wasn’t there to contribute to the team.