The rookie small forward was barely a few months old when Bryant entered the NBA 20 years ago to embark on one of the most decorated careers in league history. Winslow, who turned 20 last week, knew he would likely have only two cracks at playing against Bryant before the Lakers legend retired.
That means Winslow is now down to his one and only shot when the Heat visit the Lakers on Wednesday at the Staples Center to open a three-game trip. Despite coming off the worst loss of his career in the Lakers' 48-point drubbing Monday at Utah, Bryant has indicated he will play in the eight games remaining for Los Angeles (15-59).
Winslow may be in a bit of awe if he hits the court against Bryant, but he vows there won't be any mercy.
"I want to be able to go home and tell my homeboys that we killed Kobe," Winslow said. "That's how you approach those games. Afterward, you can reflect. But in that moment, you're trying to get after it a little bit. So you [finally] get a chance to play against the best, growing up as a kid a person you idolized."
Sure, that's tough talk from Winslow. But make no mistake about it: The second Wednesday's game ends, it'll likely be tough to get past Winslow in the line that forms around Bryant as Heat players seek one final moment or piece of autographed memorabilia from the five-time NBA champion.
But a knee injury could threaten Winslow's availability after he suffered a minor strain late in the fourth quarter of the Heat's home win against Brooklyn on Monday. Winslow, who traveled with the team on Tuesday, said after the game that he expected to be available against the Lakers.
The chance to spend even a few possessions defending Bryant would be the culmination of a magical month for the Heat's rookie swingmen. Both Winslow and Josh Richardson could end up with the assignment at various times Wednesday during their stints off the bench. Their rapid development over the course of the season, particularly in March, has been a key reason why the Heat (43-30) have won 14 of 20 games since the All-Star break and are in contention for the No. 3 playoff seed in the East.
Winslow's minutes, scoring, rebounding and shooting percentage have all increased over the past 20 games from his production prior to the All-Star break. Richardson, who has solidified a role in the rotation after two stints earlier this season in the D-League, is having the best 3-point shooting month in franchise history while knocking down 63.5 percent of his shots from beyond the arc in March.
While Winslow has been a regular player in the Heat's forward mix all season after being selected No. 10 overall in last summer's draft, Richardson's emergence has come since the All-Star break. A second-round pick selected No. 40 overall, Richardson has excelled at both guard spots and has scored in double figures in eight of hsi past 10 games. Despite his hot shooting and consistent scoring punch, the most impressive numbers from Richardson's stat line from Monday's game was that he played 38 minutes and committed just one turnover as he filled in for an ailing Goran Dragic as the starting point guard.
"They're fearless, so you're happy for those guys getting rewarded for the effort and the toughness that they've consistently played with," Heat coach Erik Spoelstra said of Winslow and Richardson. "They will compete toe-to-toe with you and look you in the eye and they're not going to back down. It's the epitome of 'We'll show you respect by giving you none.' They're gaining a lot of confidence because the veteran players now have a lot of confidence in them, and that's a powerful thing."
That confidence and swagger have been on full display this month. Exactly this time a year ago, Winslow was a freshman leading Duke to an NCAA championship. Richardson, on the other hand, had just completed a disappointing senior season at Tennessee and was struggling to line up invitations to pre-draft workout camps. Now, they're both critical components to Miami's push for the playoffs.
"I'll just tell them, 'Good luck,' because Kobe is going to go at them when he gets the opportunity. I'll tell them to go out there and enjoy it."Dwyane Wade on his advice to Winslow and Richardson
"I wouldn't really call myself and Justise rookies anymore," said Richardson, who has made at least one 3-pointer in 13 of his past 14 games. "We are just basketball players. We feel like we are big parts of this team, and we feel like we can bring a lot to the table. It's all just added up."
Winslow and Richardson may no longer consider or conduct themselves as rookies. But that doesn't mean they're too mature and cool to be starstruck. Bryant tends to have that impact on young players, especially those who grew up wearing his jersey or using his likeness in video games.
Last week, Phoenix rookie guard Devin Booker had 28 points and seven assists in his matchup with Bryant, who missed the first three games between the Lakers and Suns earlier in the season. Afterward, Booker snagged a pair of Bryant's autographed basketball shoes.
"It's just something I will remember for the rest of my life," Booker, 19, told reporters after the game.
On the other hand, Heat star Dwyane Wade has had more than a decade of showdowns with Bryant, and they were considered the top two shooting guards in the league for many of those years. Wade never got the chance to experience what this season's rookies are going through in their hello-farewell exchange with Bryant. Wade, a Chicago native, was hoping for the same brief career overlap with Michael Jordan, but the iconic Hall of Fame guard retired the season before Wade was drafted in 2003.
"I wanted it, but I would have been nervous as s---, no matter if MJ was 35, 45 or 55, simply because he was Michael Jordan," Wade said. "But that would have been a cool moment."
So what is Wade's advice to Winslow and Richardson if either gets matched up with Bryant?
"I'll just tell them, 'Good luck,' because Kobe is going to go at them when he gets the opportunity," Wade said. "I'll tell them to go out there and enjoy it."
Composure has never been an issue for Winslow, who has defended LeBron James, Paul George, James Harden, Carmelo Anthony, Kawhi Leonard and more already this season without flinching. Yet even in the final games of a career sputtering to the finish, Bryant represents a unique challenge.
"He's the Mount Rushmore -- and there's not too many Rushmore guys out there," Winslow said. "Kobe don't care that I'm a rookie. He's going to go at me like I'm anybody else. Once we're between those lines, he's just a shooting guard and I'm just a small forward. But, yeah, afterward I'm going to try to get something from him to bring back with me."