I am not going include the 1990s and prior guys as I just don't remember enough of them and it's tough to compare across generations. Given their HS success, I assume Pre, Virgin, and Lindgren all would be T5-10 guys in a race like this, but who knows where to put them. But in a hypothetical of the 2000s, 2010s, and 2020s, here goes my best guess based on how all these guys ran/their fitness level in their respective best seasons/postseasons races (5 from each):
2020s - Sahlman, Wolfe, Young, Young, Hough
1. Dathan Ritzenhein -- nobody has dominated HS cross country running, particularly against guys like Webb/Hall, as Ritz. Nobody has come within 39 seconds of his 14:10 in Michigan since, despite guys like Hough, Kessler, and Fisher. His FL performance against Webb was probably the best run by a HSer ever (highest speed rating I am aware of -- his 214 there is considerably better than something like Young's 205 in 2019).
2. Edward Cheserek -- as close to Ritz's dominance as it comes, but he was more of a racer so I'm not sure we ever saw just how fast he could go if pushed. Challenged Verzbicas when he was just a sophomore (2nd at NXN), easily won in kicks at FL both the next years. Highest rating of 208 (207 @ FL).
3. Lukas Verzbicas -- up there with the dudes above him. 2x champ, pretty much untouchable, and tended to dominate. Not sure of his highest speed rating.
4. Chris Solinsky -- absolutely crushed a great field in 2002 - speed rating of 212 (3rd highest ever to my knowledge).
5. Matt Withrow -- very underrated on here, it seems. Two of the fastest speed ratings ever (207 @ FL, 207 @ FLR). Beat one of the greatest fields of all time in taking down Rupp, Kiptoo, and True. Deserving of this spot.
6. Grant Fisher - another 2x champ with fantastic speed ratings (206).
7. Drew Hunter -- one of the best FL performances in recent memory (207). Obvious huge talent.
8. Nico Young -- dominated a great field at NXN. Speed rating of 205.
9. Mike Fout -- very underrated, but put up one of the greatest performances and speed ratings at FL his senior year in taking down Chris Derrick and German Fernandez (210).
10. C. Sahlman -- Very tough to compare the Garmin RL course to any other. HIs speedrating at RL was a 203 so I'm using that as a guide.
11. G. Fernandez -- Best of the non-champions given his terrific 209 at Woodward, which withstood the challenges of Nico Young and Colin Sahlman.
12. P. Wolfe -- COVID certainly limited his ability to show off in his best year -- would have liked to see what he could do on some classic courses. Oh well.
13. Leo Young -- Just behind Sahlman all year.
14. Lex Young -- Same
15. Riley Hough -- Won FL, hard to know if RL was just a down race or if the NP guys are fitter.
By speed ratings, the 2020s decade dudes just don't compare, but speed ratings do have their flaws. Still, given that none of the NP guys could beat German's times and Sahlman is the only champ of the group, I think it's a fair order.
Chris Derrick probably has an argument to be ahead of Fernandez. He has a 208 speed rating from FL when he lost to Fout. Alan Webb was pretty dominant in 2000 but for getting pulverized by Ritz at FLN, but he could arguably be above Fernandez as well, I suppose. Fout might have some legit beef with being 9th as well given his amazing performance and competition that year -- could see him being 6th or 7th, but I give Fisher the nod for being a 2x champ. Can't solve every issue, but if you move Fout to 6th the older dudes probably win.
Final Team Scores:
1. 2010s - 26
2. 2000s - 30
3. 2020s - 64