When asked if he believes Mayweather should step back into the ring, a move that could be in play with the UFC, Jackson says he has too.
"I think he got to right now because the money's gone," Jackson said to host Ebro on Hot 97.
"It's fight, get the money, spend the money, fight."
Stunned by the revelation from the rapper turned television producer, Ebro pushes back on just how all that money could be gone.
"Is it just his overhead is so high on a day to day, month to month," Ebro asks.
"With the lifestyle that money's gone. Trust me. Now it's like if you call him he'll be at your local nightclub because he needs that action right now," Jackson responds.
The two men used to be close friends before an ugly feud erupted and saw them trade barbs in a very public manner on social media.
As the blows continued to get nastier and nastier between the two men, Mayweather recently spoke about being blindsided by the ugly war of words.
"If this man [50 Cent] comes over to my house, my chef cook big meals for us. We sit back, we kick it. We travelled on the jet together," Mayweather said on the Drink Champs podcast.
"This is coming out of the blue. It's like me and you just kicking it, I'm right here talking with y'all, I come and do the show with you every day, and then one day, you just go out of the blue and I'm like damn, 'Where is this coming from?'"
Mayweather has reportedly been in talks with UFC boss Dana White about a megafight in 2020 following his blockbuster bout with McGregor in 2017.
Mayweather, now 42, was competing for the first time in two years but he was not fazed by the knockout power his opponent was showcasing in the Octagon.
The American gave away some of the opening rounds, taking the occasional left hand or pawing jab, before stepping on the gas and stopping an exhausted McGregor who, despite amateur experience, was boxing as a pro for the first time.
Mayweather was so confident heading into the fight he did minimal training before the bell rang.
"For Conor McGregor, I didn't really train," he said on the Drink Champs podcast.
"All I did was do push-ups and sit-ups. That's all I did. Push-ups and sit-ups, box a few times, hit the bag a few times.
"Because, actually, the training camp was in different places.
"I would do a training camp in Vegas a few days. Sometimes I wouldn't go to the gym for a week.
"I took it serious. Like I said before, I wanted to have some fun in the fight. I wanted to entertain the people."