A general manager needs many traits to succeed in the NBA.
It's about much more than just knowing basketball well. General managers have to be great communicators and negotiators. They have to think several steps ahead and be innovators.
But perhaps most importantly, they have to be aggressive. All those hours on the phone can lead up to one moment, and the best general managers know exactly when to push their chips in and go for it.
Aggression doesn't always relate to success, though. It needs to be paired with a keen sense of self-awareness and a defined direction, lest it become reckless.
Being a GM is a little like being a high-stakes gambler in a way. There are ups and downs, but it's about the process and not the result.
With that in mind, let's take a look at the gambling personas of the league's most aggressive general managers.
Nickname: The Protege
Most Notable Move: Traded Jrue Holiday and Pierre Jackson to the New Orleans Pelicans for Nerlens Noel and a 2014 first-round draft pick. Full track record here.
In the movie The Color of Money, a young pool player learns the tricks of the trade from the original hustler. In that same vein, Sam Hinkie has soaked up everything that Daryl Morey taught him during his time in Houston and has come out firing with a few big deals in his first season in Philadelphia.
While some general managers let their teams stumble for years before pulling the plug, a few have the foresight to see they're going down the wrong path. Hinkie's first step when he got to Philadelphia was to tear it down and stop chasing the eighth seed every year.
That takes some guts, and not every GM would be able to do it.
For Hinkie, it's been all about maximizing the chances to select star young players in the draft and trusting the rebuilding process. Here's what he told LibertyBallers.com earlier this year about his perspective:
"We can't control [the results]," Hinkie said. "I don't know any other benchmark [than evaluating process]."
"It would be like you sit down at a blackjack table and you say 'forget how you play, how many hands do you have to win to know you're doing what you should be doing?. If you win seven hands, is that enough? Or do you have to win eight hands?" Hinkie said in a comparison. "And you say, 'actually all you should focus on is what we know will lead to winning hands in blackjack over time.' "
So far, he has done just fine out from under the wing of Morey. Michael Carter-Williams has been brilliant, and the New Orleans Pelicans look primed to offer up a top-10 pick this year in addition to Philadelphia's own choice. We'll see what Hinkie does at the trade deadline, but don't be surprised if it's another big move that pushes the Sixers even further down the path he chose.
Nickname: New Dealer
For years and years, the Warriors seemed to be stuck at a blackjack table with a ruthless, cold dealer. Bad luck and lost money ensued, but after hiring Bob Myers in April 2012, a lot of that has changed.
After years of incompetent management, Myers has quickly earned the trust of the Warriors faithful with a series of impressive moves.
Whether it was selecting Harrison Barnes and Draymond Green in his first draft, trading for Jarrett Jack, landing a perfect fit in Andre Iguodala despite having no cap space, taking a risk on the health of Andrew Bogut or picking up Jordan Crawford for nothing, every big move he has made has worked out so far.
He's dishing out winning hands all over the place.
One of the signs of a truly aggressive general manager is that he doesn't just fold up when his flexibility is limited and his team is successful.
Myers could have went into the year without Iguodala, but the trade has catapulted the Warriors into title contention instead of being just another playoff team. When there was an issue with the second unit this season, he addressed it.
He may not be deep into his tenure as Warriors general manager, but he's made it clear that he'll be plenty active in that role.
Nickname: On Tilt
Most Notable Move: Trading Tobias Harris for J.J. Redick. Full track record here.
It's not that John Hammond doesn't know what he's doing. His recent draft history (Giannis Antetokounmpo, John Henson, Larry Sanders) suggests the exact opposite. It's just that when something goes wrong, he is prone to making big moves to try and rectify the loss.
He gets on tilt too easily.
The Milwaukee Bucks haven't been mediocre for so long because of inactivity. Hammond has made multiple aggressive moves to try and get his team out of the mud, but the big ones (the trade for Monta Ellis, the deal for half a season of J.J. Redick) have been reckless deadline moves that felt more reactionary than planned.
After again signing veterans like Zaza Pachulia and perennial under-achievers like O.J. Mayo this offseason, the best thing may have happened—the Bucks finally fell completely flat.
Milwaukee is screaming for a rebuild, even if the prospect of that is unappealing to Hammond's boss, Bucks owner Herb Kohl:
“In our organization, there is this competitive need to be as good as we can every year,” Bucks owner Herb Kohl told Bleacher Report's Howard Beck. “It’s an instinct. Even though one might argue that mathematically you’re better off going the other way.”
Hammond has been one of the most active general managers at the deadline and in free agency over the years, but here's hoping for Milwaukee's future that he sits out a few hands and stops trying to win everything back with one move.
Nickname: Double Down
Most Notable Move: Trading for Tyreke Evans this offseason. Full track record here.
Don't ask Dell Demps if he'd like to double down, because he'll do it regardless of the circumstances. After seeing how damaging it was to have one injury-prone, high-usage guard with a big contract on the roster in Eric Gordon, Demps traded for the exact same thing in Tyreke Evans, despite already acquiring Jrue Holiday.
Demps has been the general manager in New Orleans since 2010, and like most GMs, there's good and bad.
The problem is that he always seems to bet on the same type of player multiple times. Austin Rivers and Brian Roberts are both undersized, shoot-first guards, and they were acquired within a few months of each other. Eric Gordon and Tyreke Evans both had the same issues and needs when signed. Jason Smith and Greg Stiemsma do the same things on the court.
Starting to see a pattern?
Demps has had a hard time diversifying the roster and filling specific needs, and the Pelicans are struggling because of it.
New Orleans has a few obvious holes to fill, but without next year's draft pick or lots of cap space, Demps may not have the chips to do it after doubling down so much in the past.
Nickname: Heat Check
Mitch Kupchak is one of the most highly regarded general managers in the game, and he's not opposed to making risky moves regardless of the team situation. Even if his trade offers aren't likely to be accepted, some of his rumored and accepted deals often feel like heat checks.
In the last 14 years, he has made a ton of aggressive deals for the Lakers. Perhaps the most memorable was his trade for Pau Gasol, which shocked everyone when it happened and netted the Lakers a few rings as a result.
There is no such thing as an unattainable trade target for Kupchak. That confidence might be misguided elsewhere, but it's perfect for a storied franchise like the Lakers. Even in hard times, there's always the hope that he will pull off something miraculous, because he's done it so often before.
When you hear certain Lakers fans coming up with seemingly impossible trades, you have to understand that he has conditioned them to do that with his prior moves. You shouldn't expect 30-foot, off-balance heaves to fall, but with Kupchak, you sort of do.
Nickname: The Gouger
Do the Celtics ever not "ask a high price" for one of their players? Danny Ainge is the master of luring teams into trade talks, and then asking for the world once he has them on the hook.
He's all about price gouging.
Just in this offseason alone, he received five future first-round picks (including the rights to swap) for three aging players and a coach. That's not bad at all, considering the writing was on the wall for everyone to see.
The Celtics somehow always seem to have the leverage with Ainge navigating the negotiation process. He blends together the ability to engage teams in talks and take them for every penny.
Ainge may not make as many actual trades as some of the other general managers on this list, but the Celtics are constantly rumored to be dealing. There's also some recent bias at play here, as Ainge has pulled off two trades already during this season and might not be done.
Of course, it's about more than just trades when it comes to being a general manager. For example, going to the college ranks to hire Brad Stevens as head coach was a bold move, but it looks like a great one.
Give Ainge a lot of credit. He flirted with the idea of blowing it up for a few years, but now that the time has arrived, he isn't being bashful about doing it.
Nickname: The Billy
Most Notable Move: Trading for Joe Johnson. Full track record here.
In fantasy leagues (or in real-life dealings, I suppose), it's always a good idea to target the owner who is most desperate and willing to sacrifice anything so long as he gets what he wants at that very moment. My friends and I call that "finding the Billy," and I'll let you guess who that's named after.
In the NBA, there's something called the Stepien Rule. Here's salary cap guru Larry Coon with the explanation:
Teams are restricted from trading away future first round draft picks in consecutive years. This is known as the "Ted Stepien Rule." Stepien owned the Cavs from 1980-83, and made a series of bad trades that cost the Cavs several years' first round picks. As a result of Stepien's ineptitude, teams are now prevented from making trades which might leave them without a first round pick in consecutive future years.
Just as Stepien mortgaged the future all those years ago, King is doing the same. After trading for Joe Johnson, he has done numerous deals that sacrificed assets. The Nets won't have a draft pick to trade until 2020, and they'll pay more in luxury tax this year alone than 29 other teams (the Knicks excluded) will in payroll this season. That's insane.
King has his reasons to do this, of course. Nets owner Mikhail Prokhorov has bottomless pockets but limited patience, and so it makes sense for King to make every effort to keep his job now by making the Nets successful, no matter the price or the future impact.
And that, my friends, is how organizational dysfunction is born through misguided aggression.
Nickname: Wheel and Deal
Neil Olshey has shown he can do it a few different ways. In Los Angeles, he stayed patient and let his assets accrue before trading them for the league's best point guard. In Portland, he turned nickels into dimes to build a bench and give his core exactly what it needed. He's a wheel-and-deal sort of guy, and nicknames that rhyme are neat.
In his tenure as Blazers GM, Olshey has shown that it pays to be aggressive, even if the moves are small. Although his biggest decision was plenty risky (drafting small-school star Damian Lillard), acquiring role players like Robin Lopez and Mo Williams for practically nothing has paid off as well.
Even when he hasn't had much to offer, Olshey has stayed involved in the trade game and has always looked for ways to improve his team. There's a fine line between tinkering and trading just to trade, but Olshey walks it well.
He is also aggressive with the media and protecting his players, too. When he was asked about the trade rumors surrounding LaMarcus Aldridge this offseason, he didn't hold any punches at media day, per Matt Moore of CBS Sports:
Oh dear God, would you guys get over it? How many -- asked and answered. Thank you, [to Chris Haynes] by the way. What else, guys? Show me a media report where LaMarcus Aldridge has said anything other than, 'I hope the team improves, I'm excited about what we did, I want to get better and I want to win.' Then we can have a conversation. Until then, let's move on. OK? Is that possible?
Olshey understands how the game is played in every sense of the word. That knowledge allows him to be as aggressive as he is.
Nickname: The Wolf
Most Notable Move: Trading Andrea Bargnani to the New York Knicks for a future first-round draft pick. Full track record here.
Remember Winston Wolfe from the movie Pulp Fiction? When things are so messy, and it seems like there's no way out of a bad situation, you call The Wolf. That's Masai Ujiri.
He brings a relatively unique set of skills to the table. While others on this list excel at acquiring proven talent or drafting well, his biggest strength is his ability to unload unfavorable contracts and clear the books.
By moving Andrea Bargnani and Rudy Gay this year, Ujiri did just that. Incredibly, he also managed to pick up a draft pick in the process. It's hard to imagine that any other general manager could have pulled that off. Former GM Bryan Colangelo made a huge mess for him to clean up, but he did it fairly easily.
The Raptors are in an odd place as a playoff team without realistic title hopes, but Ujiri has improved both the present and future in Toronto. Based on what we saw in Denver in the past and what's transpired this season, Ujiri is probably the best salesman in basketball right now.
Naturally, that requires a lot of well-placed aggression.
Oakland Athletics general manager Billy Beane has "Moneyball"—his way of battling the uneven playing field in baseball by exploiting market inefficiencies. Houston Rockets general manager Daryl Morey has "Moreyball"—his way of building a competitive roster while maintaining flexibility.
While fit is important for NBA teams (see: Pistons, Detroit), flexibility is king. Morey's ability to keep the books clear while acquiring assets for a big trade was lambasted by some, but it paid off handsomely with the James Harden deal. Once Harden was in place, everything else followed, including a deal for Dwight Howard.
At multiple stops along the way, the Rockets could have pushed in too early. Morey's ability to stay patient but busy and continually stockpile draft picks and valuable young players is the way it's supposed to be done.
Perhaps no general manager has been as aggressive in building a title competitor as Morey. Typically, a team has to luck out and have a franchise player fall in its lap via the draft, but he didn't have that luxury. He didn't have an owner who was willing to go over the luxury tax and spare no expense, either.
The Rockets are one of the more uniquely built teams we've ever seen, and that's because they have the league's most aggressive general manager pulling the strings from behind the scenes.