The basketball world was intrigued when news broke in February that Jennings had signed with the Wisconsin Herd, the Bucks' G League affiliate. He was claimed off waivers after a brief stint in China.
They were intrigued because Jennings is not just another player.
Before Emmanuel Mudiay skipped college to play pro overseas before coming to the NBA, long before LaVar Ball took sons LiAngelo and LaMelo to Eastern Europe, Jennings did it first. His decision to forgo his college eligibility to play professionally in Italy with Lottomatica Roma in 2008 was a bold move.
That was not the only thing that set Jennings apart. Before Under Armour went all-in on Steph Curry, it hitched its first basketball wagon to the 19-year-old Jennings. UA signed him to a $2 million contract before he began his lone season in Europe. It was a deal that paved the way for UA to become more of a household name when Jennings began his NBA career one year later. He was taken 10th by the Bucks in the 2009 draft.
When he entered the NBA as a 20-year-old, Jennings was a dynamic scorer who could penetrate with lightning-quick speed and create for teammates. This was a guy who averaged 16.6 points through his first five-and-a-half seasons, including a 55-point explosion seven games into his rookie year. He could get buckets seemingly at will.
But that promising start to his career was interrupted January 24, 2015, when Jennings, who had been traded to the Detroit Pistons in 2013, tore his left Achilles in a game against the Bucks. He would have surgery to repair the tendon and began rehab not long after.
"That was my first serious injury," Jennings recalls to Bleacher Report. "I tried to rush myself back because I was on the last year of my contract. I was trying to show people that I was the same player, but I still wasn't comfortable."
What happened next was a two-year odyssey that saw him split time between Detroit and Orlando during the 2015-16 season and New York and Washington the following season. His court time dipped to around 20 minutes per game, and his production took a hit. Jennings averaged seven points per game during that stretch and scored a career-low 3.5 per contest in his 23 games as a Wizard.
He still didn't feel 100 percent, and that affected his confidence. When his contract expired at the end of the 2017 season, Jennings had some big decisions to make.
"I told my agent I wanted to go to China," Jennings says. "China was my decision. I felt it was a good place for me to get back into the flow of things. I could find myself again and be who I am."
Packing his bags and catching that plane to Taiyuan to play for the Shanxi Brave Dragons in the Chinese Basketball Association put his career back on track. Having not worked out much the summer before he left, Jennings used the relative isolation of his new team to get back into shape.
"The Achilles injury was one of the toughest times of my life," Jennings says. "I couldn't really do the things I was able to do before. Being in China … being away from the world just helped me out. It was my second time playing outside the country, and I … was able to get back to playing basketball and having fun again and not worrying about anything."
Jennings seemed to find the fun in his game again. In his 13 games in China, he averaged 27.8 points, 5.1 rebounds, 6.8 assists and 2.7 steals in 35 minutes per game. Due to league rules regarding non-Chinese players, he came off the bench but still put up starter stat lines. He hung 29 points, six rebounds and eight assists in his Brave Dragons debut. Two games later, he put up a 36-point, eight-rebound, six-assist, five-steal performance. That was followed a couple of games later by a 42-point performance against Stephon Marbury's team, the Beijing Fly Dragons.
Jennings had five games of 30-plus points in China and looked unstoppable. His confidence restored, he was ready to make another move back across the Pacific. He received his release from Shanxi in December and returned home to California. Then came the G League offer from the Bucks.
"I knew coming back from China I'd have to work my way back up," Jennings says. "The Bucks gave me an opportunity. A lot of guys wouldn't even want to play in the G League because of ego." But Jennings just wanted "to play … to prove that I can still score, I can still pass, I can still go get it and I can still run a team."
Having averaged 21.4 points and 7.6 assists in seven G League games, Jennings says he's ready to take full advantage of his return to the NBA. With both Matthew Dellavedova and Malcolm Brogdon out with injuries, and with 40-year-old vet Jason Terry the lone true backup in the backcourt, Jennings could be thrust into the rotation immediately.
Since more teams are shooting from deep and playing at a faster pace, a trend that suits his game, Jennings can't wait to go all out now that he's back to his old self. At the same time, he's being realistic. He knows he's going to have to find his place on the team, like he had to as a rookie. And he's perfectly happy with that.
"I know for sure I'd probably have to come off the bench, but I'm better able to deal with that now, which is fine," Jennings said while still with the Wisconsin Herd. "As far as being a starter, I don't know if that will ever happen again. … Whatever a team needs, I'm down for it."
Whether this stint leads to a more stable situation for Jennings with Milwaukee or another NBA team is unclear. His play will largely determine that.
But for the time being, Jennings is happy to be back in the NBA.