Five years removed from their last playoff appearance and goodness knows how far away from their next one, the Orlando Magic flipped their front office. Out went general manager Rob Hennigan, who was hired at age 30, and in came president of basketball operations Jeff Weltman and GM John Hammond, who have each spent nearly 30 years working in the NBA.

Those two veterans have begun a period of evaluation after last season's promise of progress turned to regression. In an interview with CBS Sports, Weltman said they will have a "cautious approach" with an eye on both the big picture of team-building and the small details of how the staff gathers information and communicates. He thinks it is management's responsibility to understand the history of "what personal and team dynamics have rolled out and unfolded in the years prior to our arrival," and he will measure this season's success by more than just wins and losses. 

"We want to bring in the right sort of people, add to the group that we have, with talented players who will play for each other," Weltman said. "We want to have fighters. We want to be the sort of team that improves over the course of the season. That comes down to character, work habits, team orientation and that's what we're looking for this year."

Under the previous administration, Orlando never developed much of an identity. Weltman and Hammond were brought in to change that. First things first, they must create an environment where their players, most of whom were inherited, can show their best.   

In Aaron Gordon, Orlando has a versatile forward with star potential who will be a restricted free agent next summer. Guard Elfrid Payton, who will also be a restricted free agent, was quietly excellent in the second half of last season. Nikola Vucevic is a solid traditional low-post center, Evan Fournier is an efficient scoring wing and rookie Jonathan Isaac could be anything. The big questions are how these pieces fit and how many of them will still be on the roster when the Magic are relevant again. For that, Weltman and Hammond will tap into their pasts and the NBA's future.

Jonathan Isaac
The draft can be a crapshoot, but the Magic have high hopes for Jonathan Isaac. USATSI

Weltman joined the Toronto Raptors' front office in 2013 as new team president Masai Ujiri's assistant GM. The front office made some changes that summer but did not blow up the team the way some fans anticipated. Ujiri kept Dwane Casey as coach and dodged questions about his basketball philosophy, saying he had to evaluate everything, keep his options open and try to establish a culture. He also made sure to mention, repeatedly, how much of a role luck has to play in the front-office game. 

The Raptors, who had missed the playoffs for the previous five seasons, started the year poorly. With a record of 6-12, they traded Rudy Gay to the Sacramento Kings and it was seen as the start of a teardown. As fans focused on a draft class that included Canadian Andrew Wiggins and his Kansas teammate Joel Embiid, Toronto's best player, Kyle Lowry, literally packed his bags before New York Knicks owner James Dolan reportedly nixed a trade. Then-24-year-old DeMar DeRozan wanted no part of a tanking team and told Ujiri as much. Then the Raptors clicked, winning 10 of 13 games and captivating the city en route to the playoffs. 

"The team came together and became the sort of team that everybody wants -- management, coaches, fans -- which is a team that is greater than the sum of its parts," Weltman said. "And when you start to feel that, then there's kind of a groundswell organizationally. We kind of sensed that. It was a lot of fun." 

If Ujiri had told people the plan was to trade Gay for four role players and then have the best regular season in Raptors history, they would have thought he was crazy. After stumbling into a playoff-caliber team, he needed to figure out if he could continue to build around that core. "The players kind of dictated it," Weltman said, and the result was been the four best seasons in franchise history before he left this offseason.

If you polled veteran executives and coaches around the league about what they hope for, Weltman says, the top answer would be good fortune.

"That could mean that the guy that you loved in the draft turns out to be even better than you thought," Weltman said. "It could be that the year that you happen to have an injury and are picking higher in the draft than your team otherwise would happens to be a great draft. It could be that a trade clicks into place in a way that you couldn't even have expected." 

The Magic's past five years have featured plenty of clear mistakes. But ambiguity (Terrence Ross, a former Raptor) and remaining potential (Gordon and Payton) still could swing the right way, with some luck.

Aaron Gordon Elfrid Payton Terrence Ross
Orlando's front office is evaluating each of its players and how they fit together. USATSI

Before taking the Raptors job, Weltman was the assistant GM for the Milwaukee Bucks under Hammond. Months before the 2013 draft, the two of them went to Greece on a scouting trip. They watched a lanky 18-year-old with an impressive feel for the game. When Hammond and his front office selected Giannis Antetokounmpo that June, they loved his potential but had no idea that he would earn playing time right away, grow into a franchise player and become an MVP candidate

"It's still coming to fruition today as I sit back and watch him now," Hammond told CBS Sports. "He's taking another step towards kind of an elite-level player in this league. When you talk about these guys that turn out to be better than you think, a lot of times it's because they're outstanding people and they have this amazing character. And you don't know them until you have a chance to live with them."

Joe Dumars' front office did its homework on Chauncey Billups before the Detroit Pistons signed him in the summer of 2002. Billups, who had been the No. 3 pick in the 1997 NBA Draft, had played for four teams in five years and was all-but labeled a bust, but he was coming off the best season of his career. 

Hammond, then an assistant GM under Dumars, did not know that signing him to a five-year, $35 million contract would lead to an NBA championship. His leadership and commitment to improvement made it into a home-run deal. 

"Think about his development as a player," Hammond said. "A high draft pick had some slippages in the league. We signed him to a mid-level contract. And he's a Finals MVP playing on a mid-level contract. That's the kind of thing you classify as overachieving, and good fortune for the organization."

Those Pistons went to six straight conference finals, winning the 2004 NBA championship. Hammond said that they "maybe coulda, shoulda had two." Without Billups, they'd have had none.

Aaron Gordon dunk
Aaron Gordon can do more than dunk, but man, he can dunk. USATSI

The Magic can only hope to find that sort of chemistry. It would be ideal if they could make a blockbuster move that changes the trajectory of the team. What they are focused on, though, is developing the young players who have a chance to be a part of defining the next era of Orlando basketball. Hammond said he knows fans can get tired of hearing executives preach patience, but most of the time it is necessary.

Magic coach Frank Vogel has spent the last month praising rookie Isaac's defensive aptitude and versatility. Isaac is a 20-year-old who stands 6-foot-11 and has the ability to defend wings, protect the rim and shoot 3s; in other words, he is full of possibility. There is a world of difference, however, between him becoming a solid role player or becoming a star, and no one -- inside the organization or out -- can possibly know just how good he'll be in a few years.

Beyond Isaac, Orlando should be pleased with how free-agent addition Jonathon Simmons has performed in his first few games. It should be encouraged by its 21-point victory over the Cleveland Cavaliers, Vucevic's 41-point game against the Brooklyn Nets and, perhaps most importantly, Gordon's improved perimeter shooting. The 22-year-old forward said he feels like a "different player," more patient and confident than he was in his first three seasons. He scored a career-high 41 points on 14 for 18 shooting when the Magic beat the Nets 125-121 on Tuesday, their third win in four games.

These are all good signs moving forward, and the Magic control all their own future draft picks to keep improving. Cap space could be tight for a few years, but that's mostly if they choose to keep Gordon and Payton. 

It is only October, though, and the front office is taking what Weltman calls a "wide-view approach." If their leadership has taken anything from their past experiences, it is the importance of humility.

"It's easy to write a blueprint, but there are other factors that are not necessarily in our control," Hammond said. "There's 29 other teams trying to win at the same time, and sometimes you're dependent on the decision of a player or it could be the luck of the lottery or it could be so many things that can happen along the way. You have to have the flexibility in your plan."