ORLANDO, Fla. -- The answer was never.
The question, however, was among hundreds that No. 2 overall draft pick Victor Oladipo will face by week's end during his NBA indoctrination as the most high-profile player competing in the Orlando Pro Summer League.
When was the last time you played this much point guard?
"Never," Oladipo responded Monday after his second summer league game in as many days as the Orlando Magic's full-time converted point guard.
Not even in high school at any point?
"No," he fired back. "I was a [power forward] at times in high school, but never at the point."
What about back in little league or rec leagues growing up?
"Nope," said Oladipo, owing a huge debt of gratitude to those listing him at 6-foot-4 in the media guide. "Never."
If expectations weren't already lofty enough for Oladipo coming in as the Magic's highest draft pick in a decade and the man to replace Dwight Howard as the face of the franchise, the former Indiana University star is now being challenged to reinvent his game on the fly these days.
A lesser athletic and determined player might feel overwhelmed and grounded carrying that kind of burden. But Oladipo is approaching the opportunity the same way he attacks the rim in transition: with relentless resolve.
"I'm a point guard, and I've got to play like one," Oladipo said, convincing himself of his role as much as the reporters surrounding him. "I've got to lead my team. I've got to make sure we get the right possession, the right play, get to the right spots. It's my responsibility to do that."
Through two games, it's been a bit of a struggle. The remarkable versatility and flat-out potential in his game that allowed him to soar to the second pick in last month's draft are obvious. He's averaging 15 points, six assists, 4.5 rebounds and 3.5 steals in nearly 34 minutes per game.
But, understandably, there are also glaring growing pains. He's shooting just 28 percent from the field and has a total of nine turnovers in his first two summer league outings.
Oladipo faced a significant test in Monday's game against Oklahoma City and Reggie Jackson, a regular rotation player for the Thunder last season who started in the playoffs after Russell Westbrook was lost to knee surgery.
If any matchup this week will provide Oladipo a true taste of what he'll face when the real games start in November, this was it. At one point in the second quarter, Jackson shook Oladipo on the perimeter, sliced down the lane and flushed a vicious dunk that rocked NBA executives and scouts in their baseline seats at Orlando's practice facility.
Jackson delivered the highlight moment of the game, but it was Oladipo's response that left Jackson with a lasting impression. The rookie pointed to himself to accept responsibility for the coverage mistake, then spent the next possessions attacking and getting to the free throw line.
"I just like his attitude," Jackson said of Oladipo. "The kid, he's going to be a good player in this league. He works hard. He's a freak athlete. He's just a hungry kid. You can talk to him and see that right away. You just have to be put in the right situation. I don't ever really see him just being done being hungry. That's the best part about their draft pick. He wants to be better. He wants to be good."
Mainly, he wants to work out the kinks as quickly as possible. Oladipo missed 10 of his 12 shots from the field Monday, but was 8-of-10 from the foul line after repeatedly finding openings in the lane on pick-and-roll sets. He also cut his turnovers in half, from six Sunday to three Monday.
"He's played in the playoffs, he's started in the playoffs. He's been in the NBA," Oladipo said of facing Jackson. "So it's definitely good to play against him to see where I'm at, physically, defensively, offensively and things like that."
If this week's mission is to show incremental progress, the Magic's coaching staff believes Oladipo is right on course. And that's despite playing with a slightly sprained right ankle he hurt in the opening minutes of Sunday's victory and then tweaked in the second half of Monday's loss. Oladipo said Monday the sprain wasn't serious enough to keep him out of the three remaining games this week.
"Vic was aggressive -- he looked fantastic at the point," said Magic assistant coach James Borrego, who is running the summer league team. "He didn't shoot it great but got us into sets, was aggressive to the rim, got us settled. I tried to put him in pick-and-roll a lot. He saw the rim, saw there was opportunities to attack. We put him in a few sets that opened up the court for him, and he exploited those. That's the growth for him. When he sees that, he's got to go."
Where Oladipo goes from here remains to be seen. The Magic still have veteran starters Jameer Nelson at point guard and Arron Afflalo at shooting guard despite a roster that otherwise reflects a team rebuilding through youth.
Orlando has had trade discussions involving both Nelson and Afflalo over the past two seasons and might revisit those options again. Oladipo's development at point guard will factor in the team's plans moving forward, but it's also likely he could be used at shooting guard next season.
But Oladipo and the Magic will follow a familiar blueprint that has seen 'combo guards' blossom at other than their natural positions. Westbrook, Dwyane Wade, Damian Lillard, Stephen Curry, Gilbert Arenas, Steve Francis and Allen Iverson are among those who have transitioned between shooting guard and point guard.
Detroit Pistons coach Maurice Cheeks was an assistant with the Thunder when he guided Westbrook through his conversion from a shooting guard at UCLA to one of the most dominant point guards in the NBA over five seasons.
Cheeks said Monday that he spent time each day with Westbrook watching film after games and practices to chart the player's progress at the point guard position. Oladipo has some of the same raw skills and athleticism Westbrook entered the league with as a lottery pick in the 2008 draft.
"It's a hard position to try to convert to because you're playing against guys who have been playing the position for a while, and they instinctively know what to do," said Cheeks, a starting point guard on Philadelphia's 1983 championship team. "And you're trying to figure out everything. It happens in time. You could see it with Westbrook. He had some struggles early on, and now he's one of the best at it. So it can be done."
Oladipo said he's been studying film of Wade's early NBA seasons with the Miami Heat. Wade played three seasons at Marquette for coach Tom Crean, who is now at Indiana. Naturally, there were comparisons to Wade throughout the draft process for Oladipo because of similarities in their size and game. Wade played on the wing at Marquette but spent his rookie NBA season at point guard in Miami.
"I watched everybody. Dwyane Wade, George Hill, Westbrook," Oladipo said. "There are a whole bunch of guys. I know that if they could do it, I could do the same thing. I know they all had to learn. It all didn't come overnight. I just have to make sure I don't get frustrated."
Oladipo was then asked if he'll be overwhelmed by the challenge.
His answer was familiar.