Oladipo entered his rookie season facing high expectations from the Magic and their fans. The franchise's highest Draft pick in eight years joined a squad which led the league in losses a season ago and with plenty of opportunities to prove himself. He didn't always meet those lofty hopes, but when he did--as in his near-triple-double to bring Orlando back from the brink against the New York Knicks--he put on a real show.
What went well
If nothing else, Oladipo has a rare mentality which drives him to improve in every area he can; that much becomes evident after speaking with him even just a few times. Professional athletes give lip service to personal improvement on a regular basis, but the way Oladipo carries himself, on and off the court, suggests sincerity.
Lest one get the impression I'm damning the rookie with faint praise: Oladipo already does some terrific things, and he's only going to get better. His speed and quickness, with and without the ball, makes him an explosive offensive player. Those skills also enable him to draw contact in the lane, setting himself up for free-throw attempts and saddling opponents with fouls in the bargain. The Indiana product shot about one free throw for every three field goals he tried, an already solid ratio which will improve as he becomes even craftier varying his speeds to further keep defenses guessing.
Although playing Oladipo on the ball probably isn't feasible long-term, given his iffy playmaking instincts, he showed some improvement as an initiator as the season wore on. His growing chemistry with Nik Vučević in the pick-and-roll suggests Orlando could have a dynamite wing/big pairing for the next five-plus seasons.
Defensively, Oladipo took some lumps as he got caught ball-watching, but almost every young player--not only rookies--struggles with the adjustment to defend at the professional level. More attentiveness on defense will serve him well as his career progresses, but in the interim, his quick hands and dynamic leaping ability enable him to play the passing lanes and help protect the rim from the weak side. Just ask Carmelo Anthony about that last point.
What didn't go so well
Oladipo proved frustrating to watch offensively, especially as a playmaker. As the season progressed, he seemed to curb his tendency to make the complicated pass, but shot selection remains a bugaboo. No matter the players surrounding Oladipo and the defensive alignment Orlando faces, the Magic should always have a better option than a long Oladipo deuce off the bounce early in the clock. And yet he took such shots with regularity. Learning to keep his dribble alive longer should help address several of his offensive shortcomings, but especially that dispiriting tendency.
One can live with Oladipo's high turnovers, to a degree, because many of them come as part and parcel of his taking on more offensive responsibility than ever at any level of the sport. What's more important, in my view, is imparting the value of getting a good shot on every trip. I don't mean to suggest that Oladipo is careless or ignorant in this way; plenty of players, youngsters and veterans alike, struggle with shot selection. Even if Oladipo eventually relinquishes some of his playmaking responsibilities, he'll still need to have a firm handle on what differentiates a good shot from a bad one. Perhaps playing with more talented teammates as the Magic continue their rebuild will release some of the pressure on Oladipo and free him to take higher efficiency shots in a role which better suits his strengths.
Throughout the season, Oladipo took his fair share of falls, a byproduct of his combination of athleticism, energy, and aggressiveness. Though he mostly avoided injury--he missed two games the whole season--taking a literal pounding on a nightly basis wears on even the greatest athletes. Oladipo addressed several times his need to learn to fall better, particularly by improving his balance. The Magic have a lot of development capital invested in the 22-year-old. It's incumbent on them and him to work together in order to ensure he remains as healthy as realistically possible for a high-usage pro athlete.
So much of Oladipo's future hinges upon what direction Orlando takes in the Draft. One presumes that the Magic will use either of their first-rounders on a ballhandler, but if they don't, then Oladipo figures to start the season as Orlando's backup at the point once again.
Regardless of what position he plays--or if the Magic even view traditional positions as relevant in today's NBA--Oladipo remains a core piece in Orlando's future. He showed glimmers of real potential, perhaps even star potential, in his first season... but at other points he looked every bit the part of a rookie struggling to transition to the sport's toughest position. The optimistic view is that the trial by fire he endured will make him a stronger player. He certainly has the disposition for that approach to have worked, but we won't know for sure until his second pro season ends what effect it had on his development. For Magic fans, that prospect is at once terrifying and exhilarating. It is, in other words, like each of Oladipo's forays to the rim.