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Well, it would clearly be absolutely awesome to play for any team in the NBA, but what team would be the best to go to? On one hand, you just got your first ring playing with the Celtics as you were the best team in the league last year. You finally got that ring and you have a very legitimate shot at repeating.
Or, you are on a fantastic up-and-coming squad with multiple up-and-coming stars. You don't have that ring yet, but the future is looking very good. But do you really want to wait?
With the Celtics, you would already have that one ring in the bag. You would have won a championship, and no one could take that pride from you. You would be playing along side three of the best players in the league in KG, Pierce, and Ray Allen.
KG is a Hall-of-Fame lock, being one of the best defenders and best post players to ever play in the NBA. It wouldn't be like last year would be your only shot at winning it all either. The Celtics are still the exact same team minus James Posey.
Posey was one of their best defenders, but they still have time to replace him. The season is far from starting. They still have time to make their team better, and even if they don't make any new changes to their team, they still wouldn't go from best team in the league to missing the playoffs. They still will be a legitimate contender for the championship for the next few years.
The Trail Blazers, on the other hand, look like they have the potential to be one of the best dynasties ever, but no one can predict the future. Some say they think the Trail Blazers will win it all next year despite their youth and inexperience, and can pull it through with talent and athleticism. Although unlike last year I think that they will make the playoffs, I don't think they will be able to win a championship.
The Blazers look like they have the team that could win a handful of championships in the next few years, but no one can say for sure. No one can predict a nasty injury to a star, or players wanting to go to different cities for money or family reasons.
If you want the championship guaranteed, you would get that in Boston. (In the playing for Boston scenario, you'd have been there last year too)
I think that if you are a young emerging player in the league I would go to Portland, because it seems very unlikely that they won't do fantastic in the years to come. But if you're an older player, you never had a ring before last year, and you won't play many more years, then Boston.
What would you choose?