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Defining terms: Top 5, as I imagine it, is not a career award. At the player's peaks, where do they rank?
Kemba is, to me, clearly #1. He had the greatest individual season, and his performance took a weak, inexperienced team (sorry Chuck and Donnell) to a place they really had no right being.
#2 is difficult. As a PG season, I'm going with Shabazz, and as an overall career, I'm also going with Shabazz (and, if we're not talking positionally, but "greatest huskies," he may be #1). But Khalid is closer here than in my initial thoughts. Dude won an NCAA tournament, and would have made the Final Four the next year if it weren't for his injury. I mean, look at the 2000 bracket: if they beat Tennessee (which they would have with a healthy KEA), they get #8 seed UNC, and then #7 Tulsa for a right to the Final Four...and then #5 seed Florida in the Final Four. They had a legitimate shot of repeating were it not for an injury. Obviously counter-factuals are problematic, but we use them all the time for the 2009 team, and so it seems fair. I guess I go with Shabazz, because his team wasn't as good as KEA's 1999 team (not even close), but KEA's team had a much tougher title game. 1999 Duke would have bitch-slapped anyone in the 2014 tournament, and would have done it by dubs as they did to everyone in their tournament but UConn. So I think this is 2A and 2B for "best PG."
The remaining choices are rough: too many good players. Marcus Williams was the best passer we ever had; Doron Sheffer was probably the best combination shooter/passer we've had; AJP was probably the best shooter we had at PG; Ricky was the best defender we had--hopefully Boat combines some of all these guys into something great for his senior year. He's definitely capable of it.
This is a valid point, but I believe it also re-enforces a larger distinction between point guards from the pre-one-and-done era and point guards from say, 2004 on. Your comment about 1999 Duke bitch-slapping anyone in the 2014 tournament is spot-on, but it could also be applied - arguably more so, given the way the bracket opened up - to 2011, 2009, 2006, etc. The 1999 team is, in my opinion, the best UConn team of all-time. How much do we factor that into our assessment? Conversely, KEA was never the best player on a championship team, and he was pretty much surpassed statistically across the board by Kemba and Shabazz. Could KEA have traded places with Shabazz or Kemba and won titles with those rosters? It's hard to say. What's more difficult to imagine is how Kemba and Shabazz's games would have translated in vastly different roster and competitive contexts. Think of how 2011 would have been different with guys like John Wall and Brandon Jennings in the mix.
Similarly, this conversation provokes another question that might challenge the way we view these players, and this program: have our point guards actually gotten better - relative to their predecessors - or is our coaching staff simply exploiting the inefficiencies in continuity and seasoning better than other programs? I'm not trying to make it sound like Napier and Walker would be ordinary players in different eras - they were both first round picks, and Kemba has evolved into a borderline top 50 player. I'm wondering, though, if there dominance over the college basketball landscape is more pronounced because of the high turnover rate, and, more importantly, whether this is a trend we can expect to continue. I say yes.