I have to admit, I was a big fan of the hire. I recall some like Happy (I think) and Sehorn were skeptical. Maybe Hermann too (FYI, I'm pretty sure Hermann now posts as Rubik). I really thought Chip would get it done here. He was Chip f'n Kelly, after all. 46-7.
For me, one of the earliest signs was when he brought in Wilton Speight. Nothing wrong with Speight per se, but he was the last guy I could ever imagine playing at Oregon under Chip. It was an early sign that we weren't getting Oregon Chip; he was going to do things differently here. (In retrospect, the cynical side of me thinks this had something to do with him wanting to go back to the NFL someday and wanting to show his versatility as a coach).
The first recruiting class was not bad. He came in late in the cycle. He was able to hold on to guys like DTR, Kyle Phillips, Stephan Blaylock, and others who had already been committed under Mora. He then got a Chip Kelly-esque speedster in Kazmeir Allen to come here over sc, and I believe he was the one who convinced Chris Murray, who was also coveted.
Then there was that first season when we won 3 games. Rebuilding or not, a 3-win season is something I had never seen before as a UCLA fan. Now under the great Chip, it happens all of a sudden. Something doesn't seem right. A big reason for it was that we lost all 3 non-conference games. Rebuilding or not, "cupboard bare" or not, when you're 46-7 in college and you come out of the gate losing five straight, something is not right.
Then there was that 2nd recruiting class (pre-NIL, mind you, so save your BS), where we thought maybe Chip would start bringing in some real horses. Where we might start to look like Oregon. This is when I knew Chip was in deep trouble (not just me, but many, many others). A lot of JAGS, more JUCOS than you would have thought, relatively unrecruited Chase Griffin as his QB signee. That Harris kid who started the Colorado School of Mines joke, and some other guys who had virtually no P-12 level offers). He brought in Yankoff as his transfer QB, after I believe Yankoff was projected 3rd or maybe 4th on the UW depth chart.
Then we had that second season. Again, lost all the non-conference games, went 4-8. Same record Neuheisel put up a couple of times, and Mora once, in the darkest of hours for the program in the post-Donahue era. Dorrell had never won less than 6. Toledo won 4 once, but that was after winning or sharing the conference title 2 years in a row. Chip has now lost more than 2x the number of games he lost his entire HC tenure at Oregon. Lest you think Chip has built his foundation and is about to go on a tear, he signs his 3rd (still pre-NIL) recruiting class.
This class is not terrible, if nothing special, but it extinguishes all hope that Chip intends to go big in recruiting and will make us a player with national-level recruits. Certainly not going to get up to peak Neuheisel or Mora level. As his QB signee, he brings in 6'7", can-run-under-the-shade-of-a-tree-all-day, Parker McQuarrie out of New Hampshire. You thought Chip was looking for the next Mariota? I give you 5'10 Griffin and 6'7" McQuarrie, and Griffin is no speedster himself. Something is not right here.
At this point, 2 years in, UCLA IMO had plenty of evidence that it wasn't going to work with Chip. That 3rd (Covid) year was weird and people didn't want to hold it against anyone, but it was uninspiring enough that UCLA absolutely should have fired Chip. Even the first-year Dorrell at CU beat his asz and had a better season.
There's a lot to look back on, but to answer my own question, Wilton Speight was when I first started to suspect something was ever so slightly amiss, and that 2nd recruiting class was when I was sure we'd been had.