Exec with the most courage

 I’ll say the Celtics F.O. They turned Rondo into a pick and Jae Crowder. They made the trade for Isaiah Thomas. They gave up two future hall of famers in Pierce and Garnett for boatloads of picks from Brooklyn. They nearly made that trade to Charlotte by giving up 7 draft picks for Justise Winslow and back in the day, they gave up nearly half their roster and a top 5 pick for Garnett and Ray Allen.

 I’ll say the Celtics F.O. They turned Rondo into a pick and Jae Crowder. They made the trade for Isaiah Thomas. They gave up two future hall of famers in Pierce and Garnett for boatloads of picks from Brooklyn. They nearly made that trade to Charlotte by giving up 7 draft picks for Justise Winslow and back in the day, they gave up nearly half their roster and a top 5 pick for Garnett and Ray Allen.

 1a- Houston- Royce White was a known risk. Beasley is an obvious talent and an obvious risk. Having Dwight and Harden as your "leaders" is risky…

1b- Clippers- Doc knew he needed more to get this team over the hump and into the SA/GS territory. He took a chance on both Josh Smith and Lance Stevenson. Both well know risky moves. Neither worked out.

I have a hard team calling Danny Ainge risky (which is why I didn’t put the Celtics here), I usually just call him smart and patient. But he does pull off a lot of trades, so I can see how he fits that part of the OP.

The Blazers are a perfect example of what to do when you KNOW your star is leaving. You start giving away your better support players for young promising players. I know Lillard playing out of his mind is a huge part of their rebuild, but credit to the frontoffice for not sitting on their thumbs for a season before LA bolted.

 1a- Houston- Royce White was a known risk. Beasley is an obvious talent and an obvious risk. Having Dwight and Harden as your "leaders" is risky…

1b- Clippers- Doc knew he needed more to get this team over the hump and into the SA/GS territory. He took a chance on both Josh Smith and Lance Stevenson. Both well know risky moves. Neither worked out.

I have a hard team calling Danny Ainge risky (which is why I didn’t put the Celtics here), I usually just call him smart and patient. But he does pull off a lot of trades, so I can see how he fits that part of the OP.

The Blazers are a perfect example of what to do when you KNOW your star is leaving. You start giving away your better support players for young promising players. I know Lillard playing out of his mind is a huge part of their rebuild, but credit to the frontoffice for not sitting on their thumbs for a season before LA bolted.

@Zouilders- back in the day, 2007, damn that makes me feel old and I am in my mid twentys. 

@Zouilders- back in the day, 2007, damn that makes me feel old and I am in my mid twentys. 

 I’m assuming you mean "risky good", not "risky bad".  For the former, I agree with the other posters — Blazers and Celtics seem to be the model.  I’ve always thought Neil Olshey got far too little credit for the Clippers becoming a good team.  Not sure why he bolted (probably Sterling at the time), but he went straight to Portland and has quickly and quietly built a good, young team while losing FOUR starters from last year.

If it’s "risky bad",  then I nominate the Nets and Lakers for making big, bold moves to mortgage their future.  As with most risky decisions, one is a genius if it works and an idiot if it doesn’t.  The results are what people usually judge, not the risk assessment behind them.  Personally, I thought the Nets moves were bad at the time, but honestly I liked what the Lakers did when they acquired Howard and Nash next to Kobe, Pau, and Artest.  I, nor I think anyone else, thought they would fail so miserably and end up at the bottom of the league.  During the trade, the picks seemed like late 1st rounders who don’t usually make it big in the league.  No one really thought they could turn into high lottery, if not #1 picks then.  Risky move, bad result.

No matter what, the Lakers will always be my team, and I think next year will prove very interesting.

 I’m assuming you mean "risky good", not "risky bad".  For the former, I agree with the other posters — Blazers and Celtics seem to be the model.  I’ve always thought Neil Olshey got far too little credit for the Clippers becoming a good team.  Not sure why he bolted (probably Sterling at the time), but he went straight to Portland and has quickly and quietly built a good, young team while losing FOUR starters from last year.

If it’s "risky bad",  then I nominate the Nets and Lakers for making big, bold moves to mortgage their future.  As with most risky decisions, one is a genius if it works and an idiot if it doesn’t.  The results are what people usually judge, not the risk assessment behind them.  Personally, I thought the Nets moves were bad at the time, but honestly I liked what the Lakers did when they acquired Howard and Nash next to Kobe, Pau, and Artest.  I, nor I think anyone else, thought they would fail so miserably and end up at the bottom of the league.  During the trade, the picks seemed like late 1st rounders who don’t usually make it big in the league.  No one really thought they could turn into high lottery, if not #1 picks then.  Risky move, bad result.

No matter what, the Lakers will always be my team, and I think next year will prove very interesting.

 but trading Older Stars for Picks & Young talent isn’t necessarily ‘Risky"…… I would call it "Smart" or Wise & we know Danny Aigne is capable & he’s got a Title…… So he’s got some "House Money" to play with………..

 Portland’s GM, on the other hand, lost a 30 y/o in his Prime Star in Aldridge……… & then promptly traded or allowed to leave 5 of their top 6 rotation players from last season….. & committed to a youth movement…. that took Real stones by GM Neil Olshy

Aldridge, Lillard, Wesley Matthews, Robin Lopez, Nicolas Batum & Aaron Afflalo were top 6 players in Portland’s rotation last season……. other than Lillard who was 24 last year – those other 5 players were All between 26 – 29 years old….. & once they realized Aldridge was leaving….. Portland rolled over that whole top 6 – 8 of their rotation…….

That took A Lot of guts….. Most teams would have panicked & tried to scratch out a 35 – 40 win season w/ the Vets who were left…. Portland rolled the dice on youngsters like Crabbe, Leonard & McCollum (22 &23 last season)…. brought in some more youth like Vonleh (20) Harless (22) Aminu (25) & Plumlee (25)….. Big Time Risk & it’s paying off….. 

 but trading Older Stars for Picks & Young talent isn’t necessarily ‘Risky"…… I would call it "Smart" or Wise & we know Danny Aigne is capable & he’s got a Title…… So he’s got some "House Money" to play with………..

 Portland’s GM, on the other hand, lost a 30 y/o in his Prime Star in Aldridge……… & then promptly traded or allowed to leave 5 of their top 6 rotation players from last season….. & committed to a youth movement…. that took Real stones by GM Neil Olshy

Aldridge, Lillard, Wesley Matthews, Robin Lopez, Nicolas Batum & Aaron Afflalo were top 6 players in Portland’s rotation last season……. other than Lillard who was 24 last year – those other 5 players were All between 26 – 29 years old….. & once they realized Aldridge was leaving….. Portland rolled over that whole top 6 – 8 of their rotation…….

That took A Lot of guts….. Most teams would have panicked & tried to scratch out a 35 – 40 win season w/ the Vets who were left…. Portland rolled the dice on youngsters like Crabbe, Leonard & McCollum (22 &23 last season)…. brought in some more youth like Vonleh (20) Harless (22) Aminu (25) & Plumlee (25)….. Big Time Risk & it’s paying off….. 

Masai Ujiri for saying "F" Brooklyn!

Actually Ujiri is an extremely conservative GM and he only makes transactions he knows he won. That’s why I like him.

Masai Ujiri for saying "F" Brooklyn!

Actually Ujiri is an extremely conservative GM and he only makes transactions he knows he won. That’s why I like him.

lol  you can argue that Danny Ainge got Billy King fired. 

lol  you can argue that Danny Ainge got Billy King fired.