Potential of Sergio vs. Webster

Last year, we learned a lot about many of our young players.  In particular, I felt we gained a much clearer sense of both Travis Outlaw and Jarrett Jack.  Though there is certainly room for debate, here's what I've concluded on these two:

Travis Outlaw: highly talented, good team fit, likely on the cusp of an absolute break-out year, potential for significant improvement still.  My conclusion: DON'T TRADE

Jarrett Jack: great teammate, fun personality, disciplined worker, but highly erratic emotionally, unable to distribute effectively on fast breaks (though he finishes individually well), turnover prone.  We have probably seen a good glimpse of what he can do and will be throughout his career: a very solid 4th-7th option on a contender.  My conclusion: GOOD TRADE for the right piece given logjam at point

So my remaining debate lies with who we'd miss more and/or regret giving up when they blossom into the big time?

Sergio or Webster

I absolutely loved both in flashes last year, and certainly both could disappear at times, as well.  However, Sergio stands at a significant disadvantage in that he averaged far fewer minutes than Webster and never fully gained McMillan's blessing.  It's very hard to say what Sergio could do with a regular 15 mpg and a steady green light from the coach.  As a point guard myself, I know that a hamstrung, looking-over-his-shoulder PG tends to disappear for fear of making mistakes.  Sergio can't grow in this model. 

Webster did a great job on many occasions and showed significant improvement over year 1.  Will he continue to stabilize and diversify his game (particularly in getting to the rim and dropping the hot-hammer)?

So my poll question remains:  Who would break your heart more if traded?