First, let me just say this is exactly the kind of thing we were asking for when we set out to create an 80’s-themed anthology. Without making a single pop culture reference, you’ve made it perfectly clear that it’s the 80’s with the white blazer, the drug use, the neon clothing, and the Binaca (which I completely forgot was a thing, btw). I love how this took a sharp turn into Twilight Zone territory, also.
As far as characterization and plot, I have nothing to criticize. So far, I’m very invested. You’ve created a really strong setup.
I know this is an early draft, and you’ll likely find and correct these things later anyway, but I’m going to point them out anyway, just in case.
I’d say 3 out of 5 of the instances of the word “had” can simply be deleted. I know you already know how to do this and are likely planning to, but for those who may benefit from an example, here it is. The things I’d delete are in brackets:
Only recently did he emerge into the light to try and climb the ladder back to the top. A few writeups about his bold new clothing line, Tude Wear, [had gotten] brought his name back out to the public[. B], but printed alongside phrases like “ahead of his time,” and “enigmatic visionary” were [the] words like “disgraced” and “scandal-plagued.” So when a lawyer, Alan MacArthur, [had] reached out with [this] an invitation on behalf of [the] an investor[-] who wished to remain anonymous until they saw the designs[-], Gary [had] agreed immediately. He couldn’t really blame [them] the investor for wanting to remain behind their curtain[.]—[H]he wouldn’t touch him with a ten-foot pole either[.]—[B]but of all places to pitch a new fashion line, Why on a fucking yacht? The light was absolute shit and the constant, subtle motion of the huge boat[-] (more a small cruise liner than a pleasure yacht) [-]caused the clothing to sway as if possessed by gentle spirits. Whoever [it] the investor was, they obviously didn’t know a damn thing about design aesthetics. [Which]This suited [him]Gary just fine [in the end]; he wanted this person’s backing and money, not their opinion. He’d make a pitch on a damn rollercoaster if they asked.
(The “W” on “Why” is capitalized in the middle of a sentence because we adhere to the Chicago Manual of Style, which calls for questions within sentences to be capitalized, in case anyone was wondering. You can learn more about that here: https://cmosshoptalk.com/2018/08/14/an-update-on-direct-questions-without-quotation-marks/ )
As a side note (to people who aren’t Chris, because I know he knows this already), I cannot stress how important it is to NOT stress about this minor bullshit when you’re putting your draft together. Passive-voice verbs are easy to resolve in editing. Don’t get hung up on the little things when you’re writing; they’re not important enough to stall your momentum. Development and characterization come first. Stylistic and mechanical issues can come last—at least until they become second-nature.
Strong characterization. Great details place the reader into the 80s without drowning them in pop culture references or screaming clues. Compelling plot.
...I got nothin' to say here. If this were on my desk, I'd keep reading.