I'll take a stab:
1. Chris Paul
In his best season, Paul averaged 15.3 ppg, 6.6 apg, 2.8 tov, and 2.4 spg. His team's success was good, he was the most important player on the team, and his win shares were 4.6. Paul's numbers mask just how good he was; the real test was what happened after he left. The team's success dropped precipitously in every aspect, wins, offensive efficiency, and defensive efficiency. Wake fans will always admire Paul for his Hall of Fame career both at Wake and in the NBA, and we will also admire him for punching Julius Hodge in the nuts, even if it did cost us a trip to the Final Four.
2. Josh Howard
Howard averaged 19.5 ppg, 8.3 rpg, and 2.1 spg. He shot an excellent percentage from two (52%) and well from 3 (37%). His win shares were 7 in 02-03. Additionally, his team had a bit more success than Paul's since they did win an ACC regular season title. Howard's usage was higher than Paul's as well (28% v. 21%), indicating that the team leaned more on him than on Paul, not surprising given the high quality of guards on the 04-05 squad.
3. John Collins
Collins' offense his sophomore season was monstrous. He shot 62% from the field and took 6.7 ft per game. 19.2 ppg, 9.8 rpg, and 1.6 bpg. His win shares, however, were only 5.6, because his defensive numbers are pathetic. Collins' true shooting percentage is 65% (!), compare that to Paul of 60% and Howard of 59%, and especially considering Collins did not shoot any threes at all it becomes apparent just how offensively efficient he was. However, the team success was not terribly impressive, and defensively Collins was merely present.
4. Darius Songaila
Songaila saw tremendous improvement his senior year, averaging 17.0 ppg, 8.1 rpg, and 2.6 apg. His shooting percentages were similar to Howard's (52% from 2 and 37% from 3), he just took fewer shots. Win shares were 5.2 and although he put up the highest numbers of his career in offensive win shares his senior season, he also put up the lowest for defensive win shares that year. That is probably the effect of Prosser.
5. CJ Harris
In my opinion, the truly lost career of the [name redacted] era. Harris' win share numbers are not good, but in his senior season he put up 15.4 ppg on shooting splits of 45% from the field, 43% from 3, and 85% from the line. His true shooting percentage was higher than Paul's at 61.6%. After Collins, Harris may be the most efficient scorer in this era.
6. Justin Gray
Unfortunately for Gray, his last year at Wake was the worst year of his career from an efficiency standpoint. However, in his junior year, he scored 16 ppg on 40% from 3. True shooting of 58% is good, but he was the 2nd or 3rd best player on a good team that year. Had he played with a competent but less talented point guard (like, Ish for example), Gray's numbers would probably look very different; playing with Downey, then Paul, then Joe Dukes probably has a big impact on his scoring numbers.
7. Kyle Visser
Visser is John Collins but slightly worse in every way. 17 ppg, 7.4 rpg, 1.4 bpg, and a true shooting percentage of 60% in his senior year are all good and place his season among the most efficient offensive performances in the past 20 years at Wake, but much like Collins he was only present on defense and not very impactful. Visser's winshares his senior year were 4.2.
8. Jeff Teague
Is this the best season by a guard? In 08-09 Teague went 18.8 ppg, 3.5 apg, 1.9 spg, and an embarrassing 3.4 tov. But his shooting was outstanding; 48.5% from the field, 44.1% from 3 (!) and 81.7% from the line. With true shooting of 61.5% and win shares of 5.6, it must be asked how this team lost to Cleveland State. There is not doubt the way this team ended its season highly influences the way Wake fans remember Teague, but his final season as a whole was simply dominating.
9. Al-Farouq Aminu
Aminu's other numbers don't really stack up with the other people on this list well, but I just wanted to point out he averaged 4.3 offensive rebounds per game. To compare, Big E 3.1 in his senior season and Collins averaged 3.8. Other than that, Aminu's shooting was not spectacular; he's more of an eye test guy. It was pretty clear from watching those teams that Aminu held the entire defense together. Consistent with that eye test, Aminue had higher defensive win shares than offensive (2.2 and 2.0) for a total of 4.2
10. Ishmael Smith
Like Aminu, Ish is not in the same tier as Collins, Howard, and Paul, but in his senior season he averaged 13.2 ppg and 6.0 apg. Interestingly, of every one I have looked at Ish and Aminue are the only players whose defensive win shares were higher than his offensive win shares (1.9 v. 1.0 for a total of 2.9). Kinda weird, considering no one really thinks about Ish for his defense. Thinking about it, that probably says more about the character of that team, which relied heavily on defense in general. Ish gets high bonus points for hitting the game winning shot against Texas in the NCAAT in dramatic fashion, and also for being generally one of the most likable players on a list of mostly likable guys.
11. Eric Williams
The first question with Williams is whether to consider his junior or senior season. They are remarkably similar, although he shot more efficiently his junior year and did other things more effectively his senior year (rebounding, assists, and marginally more ppg). Arbitrarily going with his junior year, which had the most team success, he put up 16 ppg and 7.7 rpg. Win shares of 5.4, are good, but he was clearly not the most important player on his team. The abysmal ft shooting (57%) drags his true shooting down to 62%; if he shot free throws as well as Collins, Williams would probably be unquestionably the best big man in the last 20 years. As it stands, one has to debate whether the slightly superior, and probably more overall versatile, offense of Collins is more important than the substantially better defensive numbers for Williams (almost twice as much defensive win shares as Collins).
12. James Johnson
James Johnson could beat up anybody on this list. He is perhaps the most balanced of anyone on this list offensively and defensively: 15 ppg, 8.5 rpg, 1.4 spg, 1.5 bpg. His offensive win shares were 2.7 and defensive were 2.6 (total of 5.3). The shooting was efficiently at 59% true shooting. A very underrated season overall, due to being overshadowed by the dominating performance of Teague.
13. Devin Thomas
The [name redacted]e/Manning haze surrounding Thomas was so thick I couldn't actually remember his name and at first remembered him as Devin Harris. I think his best season is mostly remembered for our collective confusion as to why Collins wasn't playing more. He put up 15 ppg and 10 rpg on good shooting (56.1% true shooting). In looking at his numbers, it is remarkable how much he improved the year Manning arrived. [name redacted] was simply the worst.
14. Bryant Crawford
Crawford's 16.9 ppg and 5.5 apg were in his sophomore year were excellent to go along with Chris Paul-like turnover numbers of 2.3 per game. If the dude would play defense he would challenge Teague and Paul for best season by a Wake guard, but his defensive win shares are the lowest on this entire list at 0.7 (offensive win shares were 3.5).
Based on the above, I rank these players as follows:
1. Josh Howard (most dominating performance both offensively and defensively, was the most important person on his team by far, and was the ACC POY)
2. Chris Paul (he wasn't the ACC POY, but he did punch one in the balls)
3. Jeff Teague (Teague's numbers are better than Paul's, but when Paul left the team the wheels came completely off the wagon)
4. Eric Williams
5. John Collins
6. Ishmael Smith (heavily weighted by hitting the shot against Texas, I almost put him over Collins just for that; it's the most fun I've had as a Wake fan)
7. James Johnson
8. Bryant Crawford (I guess I value offense more than defense)
9. CJ Harris (see above)
10. Al-Farouq Aminu
11. Darius Songaila
12. Justin Gray
13. Kyle Visser
14. Devin Thomas