The playoffs haven’t been sniffed in five years. Tens of millions of dollars have been spent on disappointing and misfitting players. Coaches have come and gone faster than it takes to ride Space Mountain at Disney World. Impulsive changes were made left and right in hopes of turning around the franchise stuck at the bottom of the Eastern Conference.

If you haven’t guessed by now, I’m talking about the Orlando Magic, who, after an extremely disappointing 29-53 season, have finally decided to shake things up and bring in new management.

Enter Jeff Weltman (president of basketball operations) and John Hammond (general manager).

Weltman has spent the previous four years with the Toronto Raptors, the last of which came as the GM. Hammond comes to Orlando from the Milwaukee Bucks, where he was well-respected and made controversial but successful draft selections such as Giannis Antetokounmpo and Thon Maker. He also won Executive of the Year in 2010. These hires should put the Magic on the right path moving forward. They were looking for tried-and-tested executives to head up their basketball operations, and they found them.

But as 2017 free agency winds down, it’s time to reflect on the new front office’s first offseason together. The first event on their agenda: the 2017 NBA draft.

The Draft

The Magic had four picks in this year’s draft, including the sixth overall selection. However, due to various trades made on draft night, they left the annual prospect pageant with just Jonathan Isaac and Wesley Iwundu.

Isaac is a tantalizing prospect thanks to his height (6’11”) and length (7’1.25″, per DraftExpress). He could potentially play small forward, power forward and center in unique lineups. Iwundu, meanwhile, is an experienced prospect, and at 22 years old, he may not have much more room for growth.

In the 2017 Orlando Summer League, Isaac showed off some of his unique skills but also struggled at times. Through the three games he played, he averaged 10.3 points, 8.0 rebounds and 1.7 blocks on 44.4 percent shooting in just under 19 minutes. He should help Orlando with his rebounding and will be a good defensive player when he bulks up and gains more NBA experience:

Iwundu logged 22 minutes per game across 10 appearances, posting averages of just 5.6 points and 3.8 rebounds while shooting a paltry 30.3 percent from the field. As an early second-round pick, it will be interesting to see if he can make the opening-night roster or ends up playing mostly in the G-League.

Because of several draft-night trades, the Magic will also have several incoming selections over the next couple of years: second-rounders in 2018, 2019 and 2020, and a future first-round pick in 2020. These choices could come in handy down the line as they continue to re-tool and rebuild their roster.

Free Agency

The Magic have had a very interesting 2017 free agency.

First, they let most of their veterans go, including Jodie Meeks, Jeff Green and C.J. Watson. And for a split second, it looked like they were on their way to a good offseason and fresh start.

But then they signed Shelvin Mack to a two-year, $12 million contract—a truly bizarre move. Point guard was already a crowded position for them, and they still have D.J. Augustin and Elfrid Payton ahead of Mack in the depth chart. Why pay $6 million for a third-string point guard? And if you think Mack will be the primary backup, that just means Orlando is paying Augustin $7.3 million to be the third-string point guard.

More problematic still, Mack can’t shoot. He’s notched a 32.1 percent clip from beyond the arc since entering the NBA. He also owns a career box plus/minus (BPM) of minus-2.5, with negative scores on both ends of the floor (minus-1.2 offensive box plus-minus and minus-1.3 defensive box plus-minus). And at 27 years old, he has more likely than not reached his ceiling. Adding him to the fold is a dumbfounding move for Orlando, a team that should be using its cap space on young, up-and-coming players.

The next (and last) power play the Magic made this summer is Jonathon Simmons. They waited until July 14 to sign him, after the San Antonio Spurs surprisingly renounced his rights and made him an unrestricted free agent. He put pen to paper on a three-year deal worth $20 million with declining base salaries and only $1 million in guaranteed money for 2019-20.

While his contract is certainly reasonable, Simmons is another poor shooter who doesn’t fit with the current Magic roster. He’s putting down 32.2 percent of his three-point attempts for his career and doesn’t possess elite ball-handling or playmaking skills.

Simmons is a good defender for the most part, which will help him stay on the floor. He posted a 0.9 DBPM and 1.13 defensive real plus-minus last season for the Spurs. He’s athletic and versatile enough to guard several positions and has had success against the league’s top stars, including James Harden during the 2017 playoffs.

However, the Spurs had the best defense in the league last season, and Simmons may have benefited from playing alongside other elite stoppers such as Danny Green and Kawhi Leonard. It will be very interesting to see how his defense translates in Orlando.

With Terrence Ross, Evan Fournier, Isaac and Mario Hezonja already on the roster, it also remains to be seen just how many minutes Simmons will get in Orlando. If the Magic want to rebuild and develop their young players properly, Isaac will be logging significant minutes at both small and power forward, while Fournier’s shooting (career 37.9 percent on threes) is important for a rotation in desperate need of spacing.

Last year’s Magic were 29th in three-point percentage (32.8). Poor shooting like that can stagnate and bury a team’s offense in today’s NBA. And sure enough, the Magic placed 29th in points scored per 100 possessions. Signing Simmons doesn’t help them improve upon that finish.

Going Forward

Worst of all, it’s not like the Magic made any or all of these moves to preserve flexibility. They’ll need to dump a ton of money to carve out max-level cap space next season—a venture that becomes infinitely more difficult if they sign Aaron Gordon and/or Elfrid Payton to extensions before then. Weltman and Hammond will have to figure out what to do with the contracts of Bismack Biyombo ($17 million per season) and Nikola Vucevic ($12.3 million and $12.8 million owed the next two seasons, respectively) to leave any sort of mark on free agency in 2018—or even 2019.

Put everything together, and it’s clear the Magic remain far from playoff contention.

Their roster remains full of contributors who don’t fit together, and they are still overpaying for role players and end-of-bench fillers. They were able to land a tantalizing prospect in Isaac, but the rest of their moves continue to stump both fans and analysts. So it’s safe to say Weltman and Hammond have their work cut out for them as they try transforming Orlando into a respectable franchise once again.

Let’s just hope they know better than to leave their secret whiteboards out in the open.

Follow Eric on Twitter @ericspyros.

Follow NBA Math on Twitter @NBA_Math and on Facebook.

Unless otherwise indicated, all stats are from NBA Math, Basketball Reference or NBA.com.