Reading through this I was a little slow on the uptake and didn’t immediately realize it was from 2015 – long before I knew this board existed and while the kid was doing his Juco freshman season. Things worked out well and I wouldn’t change a thing, but I would have been a much better-informed parent if I’d stumbled across this site while the kid was in HS.
As for the question “When did you know?” I’ll answer roughly 8 years late:
He was way better than average in rec ball 5U-7U and the only thing we knew was he had an opportunity to make all-stars.
From 8U-14U we thought he had a chance to play in HS, he was middle of the pack of the better players in the area entering HS, but also late to develop.
In HS (5A) he didn’t make JV as a freshman, he played on the sophomore team. He made varsity as a sophomore and started at a corner spot for three seasons (he had a huge growth spurt, something like 75LBS over the 4 years). We had no clue about college until his incoming senior summer when a scout for the Diamondbacks told me he was a D1 talent (no pro ball interest out of HS).
He wasn’t academic focused at that time and is dyslexic, a 4-year D1 seemed improbable. So, during his senior HS year, he did an individual tryout as 2-way player at Hill College Juco (a friend’s son was playing there). They offered him and he accepted before he left campus (I wasn’t there). He still did a Blinn Juco camp the following week (just for fun), I did attend that one. This is probably the first time since the early days I notice a difference between him and most of his peers. He hit a couple out during BP, held low 90’s during his pen and had some amazing infield throws (they offered, he declined). After this, I started to realize he might play in college.
I thought he might play beyond Juco when the Padres tried to draft him late rounds after his freshman Juco season (about 12 game innings for the season, touching 94) – he declined. Literally the first week of his soph Juco fall during scout day he put up some 97’s and a week later he’d verbally committed to Arkansas (full ride, and I wasn’t involved, at this point I didn’t even know they were a baseball school). Later that fall he pitched at an area Juco all-star event and LSU was on phone before he left the parking lot. This was when I realized that he was doing well at this baseball thing.
After his soph Juco year he did get drafted by Boston in the 18th and against my advice turned them down to go to Arkansas. I knew he’d get an opportunity to play at Arkansas when they converted him from a Juco closer to a weekend starter – he ended his single Razorback season as the Friday night starter and was drafted by the Yankees in the 3rd round 2017. At this point I had a pretty good idea he’d get his opportunity at the brass ring.
IMO, pro ball is harder on a parent than any other level, there is no team until they reach the goal. Yes, they play on teams in the minors and being a good teammate matters, but it’s about individual achievement not team achievement. By the end of the 2nd year with the Yankees he was the #8 in the organizations prospect list. I was feeling positive about his chances, but a small injury and not playing the COVID season he’d fallen off the orgs top 30 prospect list. Going into his 5th pro season I knew I didn’t know anything besides how badly my son wanted it, and how I could only offer support (mostly keep my mouth shut). He was rule 5’d by Cleveland, got some things figured out and managed to stick all year. When he completed his second MLB season, I knew he was a MLB ballplayer and has a chance to play for a bit if he stays healthy.
Partly due to ignorance, partly due to the way I’m built I never looked too far out or “knew” too much. The whole journey is so fragile/special, and my goal was not to be disappointed when it ended. My son’s goal was always the brass ring, so I guess that makes him a unicorn – in the words of Russell Wilson’s dad, it's got to be someone, “Why not you?”.
Sorry for the long post, it’s nice to walk memory lane sometimes. The things I would leave for parents just starting this journey (regardless of where it ends), is stay in the moment, there are no guarantees. Don’t leave your kids with any negative lifetime memories surrounding your involvement. Be realistic, and listen to impartial input (not family, friends or anyone who’s making money on you) and try not to “know” anything…
Hit'm where they ain't, unless my kid is pitching.