So what exactly does this imply?

I have a friend online who I've always viewed as good at chess but thought he was simply talented at board games and had a competitive drive. Recently I've gotten into chess myself, and he's reciprocated and been playing more with people he knows irl apparently.

Anyway, after talk and circumstance setup some matches between him and a friends' friend who was apparently really good(not that I doubt it, I didn't watch this match nor would I be able to tell) and captain of his highschools chess club, his interest grew a lot more when he found that he won 8 times. The guy in question attests to this so I don't really see any reason he'd lie.

Talk led to him facing another friend's dad online, who was apparently Class A ELO at one point. Two games, one he drew, the second he won. Again I didn't watch, but the friend attests to this so yeah.

Anyway sorry to get so roundabout with this, but the past week I've been trying to get better through playing various Chessmaster personalities. At some point my friend insisted he wanted to play the harder personalities, and so we did. In a match that was timed 40 minutes for both sides(which seemed reasonable for the computer to have as much processing power as needed), he beat a 2400 personality named Natalie. Then, it gave the option of playing with the last opponent, the Chessmaster, which apparently has a rating of 2989.

Today, I transcribed a game that gave both sides four hours(he's pretty masochistic it turns out), and watched my friend come to a pretty decisive win. For reference, it was 10th edition and my computer runs 2.8 gh quadcore. So given the time constraints and my relatively strong computer, I would think that the computer played to mostly the best of its ability.

Sorry for the long post, but I mean, I just gotta ask if this means anything. Obviously I'm not going to believe that he's 2989, which would put him above Kasparov apparently. I don't know if it'd even be close. But I want to know if this factors in at all in judging if he could possibly be master level.

Well first off, if you know your friend's first and last name, give it go at the website linked here.  Your friend doesn't have to be rated to be good, but this is a great place to start.  Lastname, Firstname

OK, so anyway, his most telling match would be with a rated player (i.e. the dad)  If a formally A class player drew the guy, then there's about a 1% chance your friend is as strong as a master (>2200), sorry.

As for the captain of the highschool chess team... I mean that sounds really impressive, but it just depends on the highschool.  The captain could have been anywhere from a fish to a master level player so that match doesn't give a lot of info on the guy's specific strength.

I had a version of chessmaster8000 something like 5 years ago that for whatever reason played pretty weak (somehow my computer was screwed up or... I just don't know).  I couldn't beat it on really hard settings (no way) but I was scoring evenly against the 1800-2000 level personalities (I was ~1300 USCF at the time).  If you have the chessmaster game, then posting it here would help us estimate the strength.

Your friend sounds like he's no fish (chess slang for beginner/poor player) but beyond that it's hard to say.  Some acquaintances think I'm "a pretty good chess player" but they have no idea where that ranks me... and no idea the amount of work I've put into it.  What I mean is you don't know if your friend has read 20 chess books and plays every day or if he's just better than beginners.  Or even if he's a great natural talent.

So anyway the dad that was formally a class A player would be a good person to ask to estimate the guy's strength.  (Or get his first and last name and look him up online here).  Also if that highschool captain had a rating that would help estimate the strength (again, just get the guy's first and last name and go here).  If he beat the top personalities on chessmaster at long time controls that, to me, doesn't mean as much.

Even better, play a few games with the guy and post them here, we could estimate his strength within a few hundred points.

I hate long posts.

 I like lots of games

Two common misconceptions among new chess players by the way.

1. that chessplayers owe their strength to being smart and clever and are probably good at other board games as well, the way you'd think of someone being good at a card game or connect 4.  You say:

First off, skill in chess is not related to intelligence in general.  Skill in chess is not related to intelligence in general.  Skill in chess is not related to intelligence in genearl.  You probably don't believe me completely, but believe me... I'm not kidding.

Chess players don't play chess recreationaly.  Or how should I say it?  To real players it's not a game like "oh it's raining outside, I think I have a chessboard somewhere, how about a game to kill some time?"  It's a skill that they practice and develop day after day, year after year, the way you would think of playing an instrument.  It's not a casual game where their skill today is basically the same as it was 5 years ago and certainly not the same as it was when they began playing.

Many times it's not noticeable to non-chess players who know them.  And maybe the chess player doesn't even go to tournaments, but he may play online every day or read chess books often, building his skill.  You think he's suddenly starting to play people, but maybe now that you've taken an interest he's talking about his chess habits more.

2. When a non-player describes a chess player as "really good"  it doesn't mean very  much.  Chess skill is completely relative (so with no reference that description is worthless) and chess skill is very deep... what I mean is player A loses to player B 4 out of 5 games while player B loses 4/5 to C who loses the same to D etc.  This can easily be done out to player J or K which may surprise some non-players.

You say:

There's a guy at my chess club who visited a scholastic club run in a library.  One of the adults that helps organize the club there asked my club-mate for a few games.  The organizer lost every game, badly, and described his opponent like "he was a chess machine."  My club-mate was rated 1300, chess skill is very relative.