It's been long-accepted that shooting guard is the weakest position in the NBA right now. This isn't to say the position is barren by any means, but the drop-off runs pretty fast from "star player" to "role player." The 2016 free agency class represents the position well in that sense, as a microcosm filled with mostly "alright" to "meh" individuals.
Naturally, with Victor Oladipo out of the picture, the starting 2-guard spot becomes something of an open question for the Magic. Evan Fournier becomes the most obvious replacement, assuming Orlando matches whatever offers he gets as a restricted free agent (we'll talk more about that in a bit), and Mario Hezonja will probably see plenty of minutes there as well.
Unless Frank Vogel intends to throw more two point guard lineups out there--Do you all remember the 168 minutes Brandon Jennings and CJ Watson played together? Because *I* remember the 168 minutes they played together--the Magic will probably need to add one more player to fill out the rotation, or to play significant minutes in the event that Fournier is made an offer the Magic can't afford.
In truth, there aren't that many "pipe dream" SG prospects, guys who would qualify as totally unattainable. Dwyane Wade, Manu Ginobli, and Bradley Beal are players I see as significantly unlikely to leave their teams for the Magic, the first two thanks to their histories with their respective franchises, and the latter because Washington will almost certainly match any max offer that's given to him. Beyond them, however, I think most of the available talents out there could plausibly consider Orlando.
Before we get to the players from other teams, however, we should address the Magic's current projected starter:
Last Team: Orlando Magic
Fournier established himself as the best long-range shooter on the team, accounting for accuracy and volume. My favorite part about his game, though, was how he made things happen on drives. Over and over again, if Fournier got into the paint, usually something good would come out of it, whether it was a finger-roll or floater of his own or a pass to an open shooter. That's backed up by the NBA's player tracking data, which shows Fournier had the second highest number of drivers on the team, while hitting the highest percentage of his shots in those situations of any non-center player.
His greatest weakness is his defense. He had the worst on-court defensive efficiency of any major rotation player (Watson and Ersan Ilyasova did worse in their limited time with the team), and more advanced plus-minus stats like RPM tell a similar story. Part of this, I think, was that he was often forced to cover small forwards when he played alongside Oladipo and Elfrid Payton, but regardless of the circumstances it's hard to consider him anything but a negative on that end.
Still, I think it should be a high priority to retain him. I have confidence that Vogel will be able to work around his defensive deficiencies, and replacing him would become an even more difficult task without Oladipo around. Keeping the best shooter on the team should be a no-brainer, unless somebody throws an insane amount of money at him.
Now for some other considerations, in descending order of expected price:
(Shoutouts to Nicolas Batum, whom I would absolutely love on the Magic, but whom I'm considering a small forward for these purposes)
Previous team: Toronto Raptors
DeRozan is the highest-priced free agent shooting guard on the market, and Orlando is reportedly interested in signing the Toronto guard. Per the linked report, he favors staying in Toronto, but he's still considering his options.
DeRozan is one of those players that you love or hate based on your ideals of a star player. On the one hand, he's established himself as one of the league's top scorers, in the sense that he can create (and make) shots for himself. The Magic don't have a guy like that, and Oladipo was the closest facsimile. His most elite skill, arguably, is his ability to draw fouls, and as Zach noted in his point guard preview, the Magic have been abysmal at earning trips to the line, near the very bottom of the league.
On the other hand, despite his career-best 33.8% shooting from that area, DeRozan has never been a solid 3-point option, and it's going to be tough for the Magic to add a player like that given the current roster. Having Serge Ibaka around helps, but there's nobody close to Kyle Lowry's skill on the perimeter to pair with DeRozan.
Personally, he's not my cup of tea. DeRozan had the best year of his career last season, in the Raptors' best season in franchise history, so there's little doubt that adding him would improve the team. I'm just not convinced he's a good value for what he's likely to be paid. Then again, the Magic very intentionally set themselves up with plenty of money to burn, and they have to spend it somehow. There are certainly worse ways to do it than signing a bona fide All-Star.
Previous team: Charlotte Hornets
Among the players I'm listing here, Lee is easily my favorite option. While his infamous missed layup in the 2009 Finals haunts many Magic fans, I have fond memories of his rookie season in Orlando, and he's only gotten better since then. Lee's impressive seasons with Memphis and Charlotte have established him as one of the league's vaunted 3-and-D types, capable of contributing on both ends of the court.
Lee doesn't have the raw stats to show for it, but his efficiency and high basketball IQ make him a more-than-good replacement for Oladipo's production. In many ways, he fills the opposite needs of DeRozan, offering good long-range shooting but little in the way of volume scoring and drawing free throws. The Toronto All-Star is the better player, but I think Lee is the better value, and has the potential to make the guys around him better with his floor spacing.
The Veteran Shooters
I've decided to group a bunch of guys all together here, not because they're necessarily of equal quality, but because they would all fulfill a similar role. We're looking at guys like Jamal Crawford, Gerald Henderson, Kevin Martin, and Leandro Barbosa. Crawford, per the Orange County Register, has drawn interest from Orlando, among other teams.
These guys would be a nice option because they offer a skill the Magic could use (shooting), while also retaining flexibility in their roles. Many of them would likely accept a job coming off the bench, which would allow the Magic to continue playing and developing guys like Hezonja.
I would be pretty surprised if the Magic didn't sign somebody along these lines, whether at shooting guard or another position, simply because some of the existing vets are out the door or likely on their way there (e.g. Ilyasova, Jennings).
The Risky Bets
One last group to round things out. This group includes the likes of J.R. Smith, Dion Waiters, Eric Gordon, and Lance Stephenson. Personally, my least favorite options among those available, but they have their place on the right teams, and Vogel holds the distinction of being the one coach to make something out of Stephenson. Perhaps he can replicate those results with another, similar player.
It's hard for me to imagine Orlando taking a flier on any of these guys, since they can't really afford to add any potential duds, but if I had to choose one, it'd probably be Smith. Mercurial though he may be, he's proven himself in the playoffs against the harshest competition, and bringing him to the team does add much-needed 3-point attempts, if only by brute force.