Reportedly will hire Dave Stewart as general manager. [9/25]

While all GM hires are difficult to evaluate from the outside, none made this winter will be tougher than this one—a marriage between an unusual candidate and an unorthodox front office.

Start with Stewart, who brings a unique perspective to the job. He's pitched in the majors, coached, worked in a front office, and served as an agent. No other GM has that wealth of experience. Obviously there are differences between those roles and GM. Stewart is used to negotiating contracts, yes, but from the other side, where a budget is less of a consideration and more of an obstacle. He's also used to recruiting players by promising them the most money, so at least some parts will seem familiar.

Stewart isn't the only odd thing about this partnership. The D'backs front office continues to take a weird, mysterious structure. It's not obvious how much power Tony La Russa has or will use in Arizona's day-to-day operations. Of course Stewart is used to working under La Russa, but that was in a player-management arrangement. This is a little different—the whole situation is a little different.

However much say Stewart, La Russa, and everyone else gets, they'll need to make a few major decisions in the coming days. Such as:

• Organizational philosophy. In the most basic sense, there are two routes to take—the quick reload, like the Marlins, or the long con, like the Astros. The D'backs are all but certain to finish with the worst record in the majors; however, they could improve organically next season through internal improvements and better luck on the injury front. That doesn't mean Arizona wouldn't be wise to shop some of their veterans around the league—Wade Miley, Aaron Hill, Miguel Montero, and Mark Trumbo would draw interest—just that this isn't as obvious as their record would suggest. Whether Stewart (or La Russa) is patient enough to punt the next few seasons, especially after a stinker of a 2014, is unclear—there are reasons why they're in charge now, after all.

• Kirk Gibson. You don't see too many managers survive sweeping front office changes. Bud Black appears to be doing so, but he's also recognized as one of the better skippers in the game. Gibson owns no such distinction. Judging managers tactically when they have a shaky roster is tough—nobody thought Joe Maddon was a genius during his first two seasons in Tampa Bay—but Gibson's issues extend beyond his problems strategically. Ken Rosenthal reported he's about lost the support of the clubhouse.

• Front office staffing. The Diamondbacks will reportedly hire Dodgers assistant GM De Jon Watson—who, in addition to interviewing for Arizona's GM vacancy this go-around, also did so back in 2011—in an unknown capacity. Beyond Watson and other external additions, Stewart will have to figure out what the future holds for Arizona's current well-regarded employees, like scouting director Ray Montgomery and assistant director Brendan Domaracki.

Regardless of how much say Stewart will have early on, he and the rest of the Arizona brain trust will have their hands full over the next few months. Their agendas, too.