Here are the junior PRs of all sub-4:00 HS milers since Webb:
Hobbs Kessler: 4:08
Alan Webb: 4:03
Drew Hunter: 4:02
Reed Brown: 4:04
Matthew Maton: 4:03
Grant Fisher: 4:02
Michael Slagowski: 4:08
Leo Daschbach: 4:03
Lukas Verzbicas: 4:04
Of these 9 runners; 7 ran under 4:05 as a junior. So anybody over 4:05 as a junior is already looking at a pretty low chance of going under 4:00, no matter how well they run in XC.
6 of them were top 3 at a national meet in XC. 4 were national champions. I'll also note that Kessler had no real national championship to attend, and pre-injury, Daschbach was the only guy in the country who could hang with Nico Young, and a clear top 3 pick.
Lastly, 7 of them had 800 PBs under 1:52. 4 had PBs under 1:50. The other two were Fisher and Verzbicas, who never ran the open 800 as a junior or senior. They were also both 2-time Foot Locker champions, which none of the current crop can claim.
So now let's look at the contenders. Sherry is the top returner at 4:03 (converted from 4:01 1600). He was under 4:05 as a junior, so that's one box checked. He was also third at Eastbay this year, so he checks that box too. His current 800 PR is 1:54, set at a dual meet. This isn't ideal, but it shows potential for maybe a 1:50 performance this year, which would set him up great to run sub-4:00. If he does that, all he needs is the right race and I think he can do it.
Martin is the next returner, also at 4:03. His 800 PR is 1:53, which is solid. However, he ran it quite a bit more than Sherry, and set that mark in a competitive race. He also failed to place top 3 at a national meet, which is a big strike. Slagowski is really the only guy who was uncompetitive in XC who ever broke 4:00 and he had 1:48 speed and a ridiculous improvement curve. Martin has a chance, but I'm gonna predict a no for him unfortunately.
Next up is Bergen, also at 4:03. If I had to give my top pick for sub-4:00 this year, it would be him. 4:03 as a junior leaves him with only 4 seconds to drop, and his 1:51 at altitude as a junior indicates he has all the speed he needs. His only knock is that he was only 4th at XC nationals, but he was also 4th at BOTH meets. That's impressive enough to give him a great shot in my book.
The other big contender is Sahlman, at 4:04. The only other returner under 4:05, he was dominant outside of his season opener this fall, and clearly is a phenomenally talented distance runner, the best in his class right now. However, his speed is a little bit less impressive. 1:53 is fine, but he will need to improve a bit to break 4:00. However, he did run that a league meet, so it may be that has a 1:50 or so in there. If so, I think he also has a good shot.
Finally, I'll mention Rheinhardt Harrison. After his 4:01 as a sophomore, it seemed a foregone conclusion that he would break 4:00 in high school. However, his races since then have been very much a mixed bag. He ran 1:51 and 4:06 in March last year, and 8:47 in early April. Everything since has been a downward trajectory though. He was undefeated this fall, but he also never really attempted to race any national level meets. Still, he checks 2 out of 3 boxes and is not really a slouch in XC, just untested. If he can figure out how to peak correctly and get in the right race when he's ready for it, I think he has sub-4:00 ability.
Of the rest, the simple fact of being over 4:05 last year nearly automatically disqualifies them from the conversation. Hough and the Youngs were impressive enough in XC that maybe they will give it a scare, but their speed is extremely worrisome (Leo at 1:58, Hough at 1:59, Lex with no time). They have the strength, but I am doubtful of their ability to click off sub-60 quarters. I also don't think anyone else has any kind of shot. The next-best candidate is maybe Izaiah Steury (1:52/4:09, 8th at Eastbay) but he seems like a pretty clear-cut "good, but not good enough" type. Maybe someone will prove me wrong, but I doubt it.