I think this is a really cool idea. But the example at the end feels pretty uncompelling (both the critique and the compliment). I expect I'd link the post to more people if you swapped it for a more straightforward one.
I had this thought too but there's kind of a problem, which is that the more compelling the example of "tall poppy", the more politically controversial which can distract from and undermine your message. I kinda think Elon Musk is the perfect example to use though. I wish the post could somehow autodetect the reader's politics and select statements about Elon accordingly.
"Elon Musk [lately seems to be going off the antisemitism deep end/does a lot of securities fraud/comes up with dumb fake ideas like Hyperloop/calls people pedos for no reason/exaggerates how good Tesla autopilot is in a way that seems likely to kill people] but I still really appreciate how he [jump-started the modern electric car industry/brought innovation back to space launches/something something Starlink].
I think it's more so a counterexample, considering his 25 year track record of consistently taking the option of being the 'tallest poppy', and succeeding and outdoing his would be 'bandits' every time.
It shows that it's possible to deflect and reflect 'bandits' into a beneficial force, even at the scale of buying a sizable tech company in SV while aiming for maximum tall poppiness.
At least two big problems I see:
Different people have different proportions of bad things to accomplishments. If you're always going to point out one of their accomplishments to balance out criticism, you give a misleading impression of what those proportions actually are.
Balancing out the bad against people's accomplishments creates bad incentives. Not every bad thing is like "doesn't treat fanfiction seriously"--if someone's doing something that's malum in se, I don't want to balance off criticism against his accomplishments--if I do that the effect is going to be that crimes by accomplished people are treated more leniently than those by regular people.
From Overcomingbias:
...
My initial proposal to solve this problem is to continue criticizing prominent people for things that you've noticed that they seem to be actually doing wrong, since this is valuable and important.
But, every time you do that, you purchase a "tall-poppy-cutting" offset. You do that by weaving in a genuine acknowledgement of one of their accomplishments that you genuinely understand and appreciate the value of, or to acknowledge that accomplishment at some other point.
Ideally it would be on a related matter to the thing you're criticizing, but the main thing is to build the target's status back up by giving them credit for their valuable contributions. This lets you avoid contributing to the dynamic where the tallest poppies growing in a system are the ones that get cut.
For example:
"Man, I think it's kinda whack that one of Yudkowsky's biggest accomplishments was writing a really popular fanfiction. It seems like he's having too much fun, considering how serious the situation is."
becomes:
"Man, I think it's kinda whack that one of Yudkowsky's biggest accomplishments was writing a really popular fanfiction. It seems like he's having too much fun, considering how serious the situation is. Although HPMOR is a pretty great read, and many different kinds of people consistently end up with substantially augmented intelligence after reading it."