Stephen Jackson grew up in Port Arthur, Texas, raised by a single mother and shaped by the tough realities of street life. He lived the struggle firsthand—and he’s made it clear he doesn’t want that same weight on his children’s shoulders. That’s why he’s always present. Whether it’s a school event or just showing support, Jackson shows up to make sure his kids feel seen, heard, and deeply loved.

His personal life has often made headlines—and for good reason. Beyond the spotlight of two failed marriages, the 2003 NBA champion is a father to five children from different relationships, a reality he openly owns. “I take full responsibility,” he once said—and that accountability shines through. One of the clearest examples came in a recent Instagram video, where Jackson was beaming with pride, cheering on his daughter Skylar.

In the video, 11-year-old Skylar walks proudly onto the court to receive a certificate, celebrating her graduation from elementary school as she heads into middle school. It’s a big moment—and Stephen Jackson makes sure she knows it. From the stands, his voice rings out with joy as he cheers, “Here’s coming the star!” and “Yeah, shawty!” when she accepts her honor and takes her seat.

Jackson’s caption says it all: “So proud to be your father. Congrats @skylarrokks On to middle. Only death can stop me from being with u every step of the way. InshaAllah. Luckiest man on earth.” That deep bond shows up in everyday moments as well.

Just a few months ago, a lighthearted video captured their playful banter. As Jackson confidently claimed that his shades help him stay incognito in public, Skylar didn’t miss a beat. With a grin, she clapped back and left her dad speechless. “Did y’all hear my daughter?” Jackson laughed. “She said them glasses ain’t hide you ’cause I can see that big old nose from a mile away.” Moments like these say it all: this is more than just fatherhood—it’s real love, real presence, and a connection that’s only growing stronger.

Stephen Jackson’s hard lessons on fatherhood and responsibility

 The former NBA champion, who has five children with five different women, has opened up repeatedly about the regret, heartache, and lessons he’s learned. However, those lessons came at a steep price: court battles, millions paid in child support, and, perhaps worst of all, distance from his own kids. “Three of them, I regret even knowing,” he admitted. “Paid millions, millions and millions of dollars in child support, and still don’t see my kids,” as reported by Fadeaway World. That’s why he keeps going back to one message for the younger generation: “Do not have kids with multiple women. Listen to me, that s— is overrated, played-out, and it ain’t what you think it is.”

It’s clear that Jackson’s perspective on fatherhood is rooted in how he was raised. He grew up in Port Arthur, Texas, with a single mom, Judyette, who never once badmouthed his absent father, even though he lived just five minutes away and didn’t support them financially, as reported by The Shadow League. “My mama didn’t do that. She didn’t talk about my daddy. She never pressed child support on him,” Jackson said. “I sought out my own relationship with my daddy because my mama didn’t demean him in no type of way.”

While she worked two jobs to keep the lights on, young Stephen helped out at his grandfather’s soul food restaurant, washing dishes and waiting tables. That kind of upbringing, Jackson says, gave him the space to form his own opinions and deep respect for his mother.

Yet gratitude gives way to frustration when he recalls the women he had children with, especially when the math doesn’t add up. In 2023, he posted a video calling out the mother of his son, saying he had paid millions in child support over 18 years, and yet his son was now asking him for $27,000 for a car. “Where’s the child support money?” he asked. “I’ve been in court a lot since I been making money. Mothers can’t get it on their own but want to take yours.” For Jackson, the situation wasn’t just about money—it was about broken trust. “Ain’t nobody worth having a baby with right now, don’t do it,” he warned.

Despite personal struggles and complex relationships, he makes it clear that being present and supportive, like cheering proudly for his daughter Skylar as she steps into middle school, is what truly matters.