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NBA free agents: Can Reggie Jackson and Brandon Jennings play together?

Can two historically ball-dominant point guards share the court at both guard positions?

Ben Quagliatia is optimistic that Reggie Jackson and Brandon Jennings can share the court. If and until it happens, I can't say for sure whether it will work or not - but I'm a little more skeptical. My reasoning is relatively simple and unpacked fully below, but in short, both players are accustomed to playing with the ball in their hands a lot; adjusting to an off-the-ball role may be challenging.

Consider this a friendly counterpoint to other Ben's analysis.