pics

I actually can't speak to Reich's experience, as I hadn't heard about this before; the only information I could find on it is this Reddit post which states somebody tried to upload his incompatibly licensed photo from IMDb. The citation in this image is to a members-only Game Changer video.

The steps are straightforward and should go as follows:

• Make sure the image you're going to use can be licensed under a compatible license – generally CC BY-SA, CC BY, or CC0 (public domain). If somebody else took it, make sure you have their consent to freely license it. Written consent is preferable if you're afraid it could be challenged.
• Make sure the image is better than the original if one already exists. If you're doing this in good faith, this next part probably shouldn't apply, but: make sure it doesn't violate guidelines on promotion, (superfluous) vulgarity, etc.
• On Wikimedia Commons, add metadata to the image such as the date taken, the author, etc. then publish it.
  • In the case where you're uploading your own headshot which you intend to use on Wikipedia, the description should probably state that you, the user, are also the subject (especially if the author is someone other than you).
• Now to get it onto Wikipedia, you'll swap the current infobox image out for the one on Commons by just changing the string in the 'image' parameter of the infobox template.
• On a technical level you're done, but on a social one, Wikipedia does also require COI disclosures and heavily discourages editing about yourself, so it's a good idea to go to the talk page and clarify that you're the subject, that you changed the image, and why you changed the image (if one existed before).

So to your question: I can't really say, because it doesn't seem like a difficult process, and I don't know how/if Sam Reich's experience deviated from it.

Edit: TIL we have an actual guide for this.

Like everything on Wikipedia, it's a communal thing that's decided by consensus based on preference and guidelines. In this case, here are reasons why the image wouldn't be selected over the existing one:

• The image in the OP likely isn't released under a compatible free license (rule of thumb is that CC BY-SA is the most strict you can use). As the subject is living or suitable free alternatives exist (in this case, both), it cannot be argued as fair use (even if it were fair use, the image's resolution would be heavily scaled down). This would preempt anything else and immediately disqualify it.
• The current image has only Ratner center frame against a plain background, whereas the image in the OP has Ratner off to the side with three other people against a cluttered background. A portion of Ratner's face is hidden behind a woman's hair, whereas most of it is captured in the current image.
• The image in the OP has distracting digital markup – block censorship and an unnecessary red circle around Ratner's face (the red circle would be left to the caption, something like "Brett Ratner (right)").
• The lighting in the OP is much worse than in the current image and even gives the subject red-eye.
• The OP image is both lower-resolution and captures less of the subject's detail.
• The image in the OP would violate neutral point of view (NPOV) by nature of intentionally using an image whose depiction of the subject is worse in every way just to get him in frame with Jeffrey Epstein.

For a living person, the considerations are mostly what you'd expect for any other application, namely: is the copyright compatible? is it neutral? does it capture the subject well? is it well-composed? it it high-resolution? since the subject is alive, is it fairly recent in order to capture how they look now? does it capture how the subject typically looks and/or something the subject is known for? Here's what the Manual of Style has to say on image selection broadly.