So let’s say that you are racing neck and neck with someone in your age group at your key race of the year. You know this person to be a total egomaniac and ass and you really want to win. Aside from relying on your fitness and hoping to be the better man (or woman), what would be some things you could do to get the mental edge over your opponent? You know, I mean really demoralize or deflate them during the race. Good sportsmanship is out. However, you are not allowed to deliberately physically harm or sabotage them (i.e. trip, shove, punch).
Creative ideas?
Tell him how much you’ve been thinking about them, how it consumes your life to measure up and beat them, mention how you even posted about it on a forum.
Yep, that would make me a little freaked out. Go get him sport.
An old road racing trick that I like is if you have a slight gap on him going around a blind corner (one where he will not see you for a few seconds) accelerate so that it appears that he’s being dropped big time in just that few seconds where he lost sight of you.
a greasy belch, followed by wiping the back of a hand across the mouth, leading to a sigh of relief and a face on nicely exaggerated SEG with raised eyebrows has worked for me a time or two.
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I was always a fan of a little light humour.
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Always look strong, no matter how bad you feel.
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When making the decisive pass, particularly on the run, make sure that you go hard to make a clean break and then never look back.
I was never big on the mental games beyond that. Just tried to race as hard and as honestly as I could.
While passing him on the bike or run:
Whistle a tune.
Worked for me, but I probably would have beaten him anyway.
The key is to intimidate them during a training session, even if you don’t know who they are in advance.
Whistle a tune.
Cool! Along the same lines, how about humming?
Here are a few suggestions sure to break him (or make hime doubt your sanity – which may be equally effective):
“I am Ironman. Da, Da, Da Da Da…”
“We will, we will rock you…”
“It’s raining men…”
“Another one bites the dust…”
“What a long, strange trip it’s been…”
“Vroom, Vroom” motor sounds
BTW, All these would be much more effective if you ride a pink bike.
Pull up next to them, give them a good once over and wink, then drop behind them. Feel free to instert a “mmm mmmm MMMMM” or a “how you doin”
“Are you OK? You don’t look so good”
Might make them think, just long enough to get a small gap 
From there you have to rely on actual talent and training to drive home the point.
“Is your helmet on backwards?”
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i’ll usually hold off on a pass until i know that I can make the pass strong and form a clean break, i just know i’m always a little demoralized when somebody blows by me and then leaves me behind, a previous poster had it right too…never look back.
On the bike just say “man, I don’t know about you but it’d bother me if my break pad was rubbing like yours is”. Or, “I’ve got an extra tube if you need one, looks like your tire is REALLY low”.
By the sounds of your post you have everything you need for the mental edge. It seems to me that you really want to beat this person and don’t think very much of them. My philosophy (and what I preach to my daughter and the kids that I coach at school) is that it is ok for people to want to beat you because you are good but it is terrible to have people want to beat you because you are an ass. Over the years I’ve been able to close the gap and bury people fueled by the desire to beat them badly because they were jerks. It is amazing how much this can help you block out the pain and reel them in. If it is just someone good out in front of you and the emotions are not there, then it can be more difficult to make yourself hurt enough to bridge the gap.
My advice … race hard, use your intense desire to beat the guy, and do what Fleck said … go by hard on the run and make it look like you are in cruise mode no matter how you are feeling. Don’t say or do anything unsportsmanlike or you’ll have the same target from them next time.
blow by him on the bike and give him one of those lance looks when you go by.
I wind up in this situation all the time in running races. My favorite tactic is to creep up right behind a person and breathe really loudly down his neck. Doing that for a few minutes can mess up the other guy’s pacing, because he’ll naturally go harder than he should. Or he’ll get annoyed and say something like, “ah, you’re trying to intimidate me, eh?” Zing! I just gave him a little oxygen debt because I got him to talk! That’s how they fall into the trap. By pressuring the competition you’ll also be able to gauge how tired he is, whether he’s likely to try to stay with you when you pass, etc. Right when you come to an aid station, yell really abruptly to startle him, and then he’ll drop his water, and it’ll all be downhill from there. Okay I’ve never done the last part, but I bet it would work. Ooh, or you could go ahead of him at the aid station and knock all the cups out of the volunteers’ hands. Act like you’re just really clumsy, and then grab the last cup for yourself.
You never want to run neck and neck with somebody. Chill out behind them until you are ready to pass, and then pass decisively. Anything else and you give them the advantage of being able to pace off of you.
Wow! Wicked tactics. If you ever come up behind me in a race, just blast on by. Heavy breathing is not necessary. I give up.
Both your “creep up right behind the person” and “knock the cups down” tactics skirt the line of the OP’s rules of not deliberately sabotaging them, though. If you’re so close behind them that you mess up their stride, that goes beyond poor sportsmanship. Knocking cups out of volunteers hands is just bad for so many reasons…
Carry a pack of Camel straights and offer him one. Run in Crocs, cutoff jeans or a polo shirt, I had a friend that degreased on of his derailleur pully wheels so it would go creak creak along. He was a CatII when it actually meant something. Used to drive the peloton nuts.
How about just going “meep meep”, jumping up, and then when you come back down hammer so hard that the road swooshes up in the air behind you. I saw that on TV once and it left the competition so demoralized that his jaw dropped right to the ground.
Victor
Having a strong run is it’s own head-game. I love it when people start looking back. After closing any gap from the swim or bike you have so many options as a strong runner: play with them until the last 100 yards, crank out a hard mile at the end… Something to think about, going into the off season.
One trick I read about the Kenyans using: after getting a slight gap, ease up a bit so the rival thinks all is not lost, then accelerate again and pull away.