Top Five What-Ifs in Orlando Magic History

What if…

V. Something out of Rob Hennigan’s control had gone Henny’s way.

Hennigan contemplates his basketball decisions over the past five seasons.

What if the league didn’t trend away from dominant inside-scoring focused big men like Nikola Vucevic. What if outside forces didn’t force Rob Hennigan to give up on Victor Oladipo and Tobias Harris for an ill-advised playoff push earlier than expected for such a young team? What if the Magic had won the lottery when Joel Embiid, Karl-Anthony Towns, Andrew Wiggins, Jabari Parker, Deangelo Russell, or Henny’s beloved international prospect, Kristaps Porzingis, were the prize of the party?

Asking, “what-if Hennigan had made better draft choices with the picks he DID end up with?” is another topic entirely. Henny generally took the best defensive prospect available, and although he missed out on a few sleepers like C.J. McCollum, Devin Booker, and Giannis Antetokounmpo, so did everybody else. Well, except for the Magic’s new pair of J’s, of course. No, this what-if is dedicated to honoring Hennigan’s honorable attempt at pulling “the process” off right under everyone’s noses.

Rob Hennigan came to Orlando with basically just Dwight Howard, JJ Redick and Ryan Anderson as assets. He turned the roster upside down, waking up Orlando from its dwightmare, maneuvering until the Magic featured Nikola Vucevic, Moe Harkless, Tobias Harris, and a few leftover fun veterans from the 2009 NBA Finals’ days. The year after, the Magic won their only lottery in the five drafts after losing Dwight, winning the second overall pick. Sadly, this class didn’t offer any obvious locks at the top of the draft, forcing the Cavs to select Anthony Bennett before Henny brought Victor Oladipo into the mix. Before the season ends, Rob signed Dewayne Dedmon to a contract for the rest of the year after completing a 10-day deal. Henny would go on to flip a veteran scorer, Aaron Afflalo, for a relatively unknown prospect, Evan Fournier, the day after drafting two long, athletic prospects, Aaron Gordon and Elfrid Payton. The summer of 2014 served as both the peak of optimism felt by fans feeling out a rebuilding process and tipping point to the downfall of the Henny era, quite evidently the worst half-decade in franchise history.

From here on out, not a whole lot really makes sense. A dice roll on the exciting prospect out of Croatia, #PaperMario Hezonja, after missing out on the top four obvious prospects in the draft is one thing. Trading MoeHark for a 2nd round pick to free up minutes for five other wing prospects before moving two of said wing prospects within the calendar year is another. Moving Tobias Harris for cap space and a hopeful playoff push from Brandon Jennings and Ersan Ilyasova, before flipping off Magic enthusiasts on draft night by trading the pick, Ilyasova, and fan-favorite Victor Oladipo for Serge Ibaka, a withering, old PF who plays the same position as Orlando’s other best player, Aaron Gordon, is a whooooooole third thing. Something was out of whack.

Maybe Scott Skiles threatened to quit midway through his first season as Head Coach, and moves were made to appease his grumpy outset on player interaction. Perhaps ownership took the side of Skiles, one of the most recognized persons in Orlando Magic history, when it came to certain basketball decisions over Hennigan, relatively a novice in the profession. With Rob’s contract ending in a year, maybe the decision to go big by trading Ola for Ibaka was the only gamble Henny had left to zig while others zag, both in hopes of making the playoffs and potentially saving his job. By salvaging the expiring Ibaka for a late first round pick and Terrence Ross, who is either underrated because of his playing time in Toronto or overrated because of his outlandish dunking ability, Henny has another talking point in his next job interview on how he made smart, incremental moves to gain assets likely to increase in value while leaving the Magic a much cleaner whiteboard than the dirty, one-of-the-wheels-is-busted, creeky-sounding chalkboard Otis Smith left behind.