NBA Trade Deadline: Power Ranking the Boldest 10 NBA General Managers

The mark of a team that does well after a good trade is a GM that isn't afraid to make brash moves.  Basketball is a bold game, and if one is hesitant to make borderline controversial decisions, then one is probably in the wrong line of work.

Take Miami Heat GM Pat Riley. Not only did he take a huge risk by putting together a unique "Big Three," but let's backtrack to 2004, when he acquired Shaquille O'Neal from the Los Angeles Lakers. Just to get the future Hall of Famer, he sent two studs in Caron Butler and Lamar Odom.

Sure enough, just two years later, the Heat took home their first NBA championship. Riley took a risk, and it paid off.

As the deadline draws nearer, let's have a look at 10 bold front office men who have showcased some ballsy moves in the past.

No. 10: Otis Smith

To be fair, Otis Smith's tenure as GM for the Orlando Magic has been less than admirable.  His trades have been odd, particularly the one that sent Rashard Lewis to the Washington Wizards for Gilbert Arenas, and he has yet to win a title.

Still, you have to admire the guy's confidence. He truly believes that his moves are helping the team, and as bad as they may be, he has never once apologized for them. This guy does his job and never backs down from his opinion.

Men like that are rare, and despite the results of his deals, I've got to give Smith the pat on the back that he's due.

No. 9: Larry Riley

Larry Riley took over the Golden State Warriors front office in 2009 and really hasn't done much in terms of improving the team. That's probably because his best trade chip is also the team's best player, Monta Ellis. Moving him is hard because of the size of his contract, so he has stayed in Golden State while the team continues to figure things out.

Still, the fact that Riley is even willing to trade his best player is bold in itself. Most GMs would hold onto their top contributor like an infant to his security blanket, but not Riley. He understands that winning comes with sacrifices, and if it means losing your best, so be it.

No. 8: Gar Forman

Gar Forman's Chicago Bulls currently own the NBA's best record, but he's still keeping busy as the deadline approaches. The reigning Executive of the Year is hungry for a ring and has been talking to the Orlando Magic about a deal for Dwight Howard. To acquire D12, Forman would most likely need to give up Luol Deng, Carlos Boozer and draft picks.

The saying goes "if it ain't broke, don't fix it," and that statement easily applies to the Bulls.  Yet Forman won't settle for anything less than a championship, and if that means trading away some fan favorites, then that's what happens. End of story.

No. 7: Daryl Morey

Morey appears to have a crush on Pau Gasol, as he has been in talks with the Lakers about trading for him the past couple of weeks. Yet the Rockets already have a solid option at power forward in Luis Scola. He doesn't have Gasol's size, but is definitely better in the toughness department.

Still, Morey is willing to trade away Scola to bring in the seven-foot Spaniard to help Houston on its playoff push. All in all, it's a good idea to bring in Gasol's championship experience even if it does mean losing Scola's tenacity. The fact that Morey is willing to take such a risk is not only bold, but badass.

No. 6: Masai Ujiri

Masai Ujiri became the GM in Denver in 2010, and at last year's trade deadline, he earned his stripes as a front office man who will not be played. He turned Carmelo Anthony's trade demand into a month-long saga complete with a bidding war between the New York Knicks and New Jersey Nets. In the end, he got the Knicks to make him the offer he wanted.

In the trade, the Knicks sent Raymond Felton, Danilo Gallinari, Timofey Mozgov, Wilson Chandler and draft picks to the Nuggets for Anthony, Chauncey Billups, Renaldo Balkman, Shelden Williams and Anthony Carter.

Believe it or not, the Nuggets went on to have a spectacular finish to the season despite losing two of their top offensive contributors, and all because Ujiri was willing to take that risk.

No. 5: David Kahn

David Kahn has been no stranger to controversy since being named GM of the Minnesota Timberwolves in 2009. In that same year's draft, he took three point guards in the first round: Ricky Rubio, Jonny Flynn and Ty Lawson. Of those three, he traded Lawson to the Denver Nuggets, and Rubio chose to remain in Spain for two years. Flynn was an absolute bust.

Still, patience proved to be a virtue for Kahn and frustrated Minnesota fans, as Rubio joined the team this year and was a key cog in its resurgence. Any other GM may have tried to trade Rubio or be resigned to the fact that he would never join the team.

Kahn did the exact opposite and held firm. Once considered to be a wacky GM, Minnesota fans are probably singing his praises right now.

No. 4: Sam Presti

Thirty-six-year-old Sam Presti may be young, but he earned his stripes as a ballsy GM last year when he filled his Oklahoma City Thunder's need at center with a metaphorical snap of the fingers. In doing so, he sent Nenad Krstic and the talented Jeff Green to the Boston Celtics for Kendrick Perkins. Shortly afterward, he signed Perkins to a contract extension.

This trade proved to be a difference maker for the Thunder, as they continued their improvement streak and made it all the way to the Western Conference Finals, all thanks to Presti taking initiative and trading homegrown talent for championship experience.

No. 3: Mitch Kupchak

Mitch Kupchak had some big shoes to fill when he took over as Lakers GM in 2000, as he was replacing former fan favorite Jerry West. He started off with his share of controversial moves, from signing Karl Malone and Gary Payton as free agents to trading Shaquille O'Neal to the Miami Heat.

That move irked some fans, as O'Neal had helped the Lakers win three titles, but it also brought in Lamar Odom, who would go on to be a key member during the team's recent championship seasons. A few years later, Kupchak traded bust extraordinaire Kwame Brown for Pau Gasol, and the rest, as they say, is history.

And to think it all started with one trade...

No. 2: Danny Ainge

Ainge has already made headlines this season in stating that if given the right offer, he would be willing to deal one of the Celtics' Big Three if it meant future success for the team. I'm sure that most GMs carry this attitude, but none have been as open about it as Ainge was earlier this year.

Throw in the fact that he traded a key piece of the team's 2008 championship squad away last year, and it's obvious that the former All-Star means business.

No. 1: Pat Riley

Pat Riley has been involved with the Miami Heat for nearly two decades, and as the team's GM, has made some ballsy moves. Forget the Shaquille O'Neal trade; here's a guy who cares about one thing: winning. Thus, he did everything in his power to make sure that the Heat not only retained Dwyane Wade, but also brought in Chris Bosh and LeBron James.

Still, that means nothing to Riley. If he felt that he would have a better shot at winning a title by trading one of those three, then he'd do so in a heartbeat.