John Hammond’s biggest mistake was passing on a trade that his draft record suggests he would have made. In 2003, as the vice president of basketball operations for the Pistons, Hammond and the Detroit front office took Darko Milicic with the second overall pick in the draft over Carmelo Anthony, Dwyane Wade, and Chris Bosh.

In an ESPN chat a year after that draft, Hammond admitted that the Denver Nuggets, who drafted Carmelo Anthony with the third overall pick, were "in discussions" with the Pistons on draft day to move up a spot and, in Hammond’s mind, take Darko at no. 2. Had Hammond taken that trade, Anthony might have had a career in Detroit, Denver wouldn’t have all the young pieces it does now, and perhaps the entire landscape of the league would be different today.

But that was 14 years ago, and though the Darko pick gets more cringeworthy by the day, Hammond has gone on to build a reputation for himself as an experienced GM in Milwaukee who has had draft-day success despite a checkered past.

On Tuesday, the Magic pried away John Hammond from the Bucks, reportedly for a five-year deal in Orlando. Per Adrian Wojnarowski’s sources, it appears Milwaukee wasn’t willing to renew Hammond’s contract, which was set to expire at the end of next season, so they allowed Hammond to interview and take the Orlando job. For the Magic, this move comes on the heels of hiring former Raptors GM John Weltman to become their president of basketball operations.

After letting go of Rob Hennigan in April, the Magic are restructuring their front office, and they just got the man who won the 2009–10 Executive of the Year award. But what kind of GM did they get in Hammond? And what does this mean for the upcoming draft?

Here’s a quick summary of Hammond’s history:

Draft Record

Hammond’s draft history as the Bucks GM following his hiring in 2008 has been above average, and despite turning down that fateful trade offer from Denver in 2003, he has shown his willingness to make draft-day trades on multiple occasions.

The Good: Giannis Antetokounmpo, Malcolm Brogdon (so far), Jabari Parker, Brandon Jennings

The Not-So-Good: Joe Alexander, John Henson

The TBD: Rashad Vaughn, Thon Maker

Hammond’s biggest claim to being a good drafter isn’t in single picks like Giannis or Parker. Rather, it’s that he has had only two top-10 picks in his nine years and has been able to find hidden gems like Brogdon. As a GM, being able to maximize value is more important than making the obvious choices.

But, of course, Hammond hasn’t been perfect in Milwaukee. Picking Joe Alexander in 2008 over players including Serge Ibaka and George Hill is a tough miss to ignore.

Trades

Hammond’s trades have also been a mixed bag. In 2012 he traded away Andrew Bogut, then still in his prime, to the Warriors for Monta Ellis, Ekpe Udoh, and Kwame Brown. None of those guys did nearly as much for the Bucks as Bogut did for the Warriors in their rise to the top of the league. But in 2013 Hammond won the Brandon Jennings for Brandon Knight swap by attaching Khris Middleton to the deal and getting a high-level role player in a trade that was centered around two bigger names.

Two years later he traded Knight away to Phoenix in a three-team deal with Philadelphia. The Bucks’ returns? Miles Plumlee, Tyler Ennis, and Rookie of the Ye — sorry, I can’t say that with a straight face — Michael Carter-Williams. Oof.

Hammond has made his fair share of faulty roster moves. He gave John Salmons $39 million in 2010 and Drew Gooden a five-year deal that same year. His decision to give Greg Monroe a three-year max in 2015 isn’t looking like the best decision ever, either. But under Hammond, the Bucks also fired Larry Drew, replacing him with Jason Kidd, who has been the perfect leader for the franchise’s youthful and lengthy roster.

There are far worse decision-makers in NBA front offices than Hammond right now, who, after nearly 30 years in the league, is as experienced as they come. From one vantage point, you can look at Orlando’s willingness to give him a five-year deal as a reflection of the value of his expertise. From another, you can interpret Milwaukee’s unwillingness to extend him as an indictment of his ability to progress or create much more than a middle-class team.

As with any GM in the NBA, Hammond’s blemishes are easy to point out, but there’s also no doubt that he has a knack for making savvy moves and finding solid draft picks. The Magic have the sixth pick in this year’s draft, a pivotal position that leaves them with a lot of options to move up or down.

The NBA is as much reality TV as it is a business. Sometimes the big, splashy moves will garner the most attention, the most acclaim, and presumed importance. But the league has also shown us time and time again that sometimes a small move, a late-round draft pick, an understated hire, or a simple decision may be the ultimate key to finding success.

The Magic’s recent years have been riddled with mediocrity, misdirection, and a lot of weird roster moves. Though Orlando’s emergence from the NBA’s doldrums is far from assured, with Weltman and Hammond now in the fold, there’s a sense of a fresh identity as well as some much-needed expertise at the helm.

As long as Orlando’s new front office keeps the cameras away from its whiteboards, the Magic should be headed in the right direction.