The Pioneer #54

A Tale of Two Peacocks

Sep 17, 2025

Did some traveling so it’s been too long since a newsletter. Feeling a little bummed about that. Unsure how to balance the life with the written word (indoor scarf of a sentence). How to write what I want but a whole lot more of it (indoor cravat of a sentence). Thankfully, my last piece in the drafts had something to do with it all (not really but I’m gonna force it).

Over the weekend (that this was supposed to come out), a friend of mine revealed he was paying for two premium Peacock accounts. Both accounts streaming on the same television. Both accounts exclusively for his own use. And such fiscal exposure in the niche streaming space undoubtedly needs newsletter explanation. A Pioneer investigation. Maybe even as I mentioned up top…a small bit of self-association.

It was a few weekends prior to this discovery that Jimmy and I first met up for a long winded catch-up at Chucho. Our bottle of natural wine had gone from orange to translucent, a night almost called, when Jimmy began looking at his phone with a sense of dread. I thought maybe he had retaken the SATs and his results were in. Maybe he’d been summoned. Maybe he was the father. So I pried. It was none of such. Instead, a text from his girlfriend Allie. Considering they had been together for a little over a year, I found it mysterious how little he’d mentioned her throughout our long-winded catch-up conversation. Finally, Jimmy looked up from the phone. His dread morphed into hollow enthusiasm and he smiled at me like Cutco Knife salesman. I knew a terrible opportunity was a front. One was, indeed. A once in a lifetime offer to join him to meet up with Allie at Rocco’s…just a hop, skip, and a freeway away in West Hollywood. Hard no, almost immediately. He kept trying. But even Jimmy knew how insane the ask was just an hour before last call. So insane, I asked him why she expected him to come in the first place. I didn’t realize that I’d taken this conversation to a point of no return.

“Allie’s great. Fun. Down to earth. I’ve just never been with someone like her….” I couldn’t identify just what he was withholding. I liked Allie a whole lot, too. Also thought she was great, fun, and down to earth. So I pried once again, peppering Jimmy with cross-examination. “She’s down to earth but…” Jimmy paused. But what Jimmy? But what? “In a different way” he finally blurted out. Then I understood. Jimmy finally revealed to me, and maybe himself, that he and Allie shared different definitions of “down to earth.” Jimmy from suburban Wisconsin and Allie from suburban Beverly Hills, earth itself was quite different.

It was a contradiction that excited Jimmy at first. He’s a prodigal talent in his field with some cash to blow and Allie’s appetite for the pasta dinners, handbags, and weekend getaways allowed him to go full Hollywood in a way I could tell he’d always wanted to. He is, as you can only assume from his dueling Peacock subscriptions, an absolute power spender by nature. In that book about love languages, he surely speaks in giving. And god bless him. I can recognize how rare his generosity is and admire it as I am far more frugal (embarrassingly cheap), increasingly narcissistic (with each new subscriber), and therefore chronically rewatching Up In The Air (aka completely alone).

But it doesn’t take a scrooge like me to identify how Jimmy’s greatest quality was becoming a weakness. A human contradiction as old as time. And that night at Chucho, Jimmy was growing tired of the fact that his love language of generosity had morphed into a love language of show up to this gay bar in West Hollywood at 1 AM because I want you to. Tensions were rising. Passive aggression was simmering. And I didn’t blame either of them. This was life the way Allie knew it, with or without Jimmy. Now, simply playing by the rules he set out. Surviving lavishly in the ruins of his love bombing. So when I said farewell to Jimmy as he entered a WeHo-bound Waymo, I sensed trouble. I just never thought it’d happen so quickly.

I got a call from him the next day. She straight up dumped him at Rocco’s. I can only assume in between the final ellas of Rihanna’s Umbrella. Understandably, Jimmy was a little shell-shocked and in need of romantic advice. And while I did once write a dating manifesto, I was in little to no position to actually give it. I’m on pace for an inaugural colonoscopy before marriage. So I spoke from the other side of the tracks and ripped a page out of the Pioneer problematic playbook. I told him whenever he was ready, to get out on the Boston Whaler, cast a line, and lightly chum the waters. Not for the purpose of hollow sexual conquest but instead to get social without a price tag. I told Jimmy to get drinks but not dinner. And if he absolutely must get a meal…split a hand roll, not the Omakase menu. By this point, Jimmy was well aware a dark side effect of his generosity. The precedents he’d set with the lavish dates. The instant commitment that’d follow. So he agreed innocent drinks with a string of dates would be a good way to avoid putting up any finish lines for himself.

But it’s hard to change.

I caught up with him a few weeks later and by god, he was surely keeping it casual. Unfortunately, his Chase Sapphire account didn’t know the difference. This is where the story gets murky. Where I start second guessing all that Jimmy told me prior and enter early contract negotiations to join team Allie over at Il Pastaio.

Somehow, Jimmy had entrenched himself in two new committed relationships. Each love bombed with toxic quantities of project green, each leveled by check offensive, and each having existed for about two weeks. Would you believe it…but both of his partners were convinced they’d just met someone incredibly special.

He took a Hinge date on a pre-booked trip to Vegas (initially for Allie). Flew on JSX. Stayed at Caesars. Dined at Taylor Sheridan’s Steak House (unconfirmed but I gotta hope). Took the other woman to a private members club screening of F1 (in Jimmy’s defense, he also took me to a screening at this undisclosed club but we kept that shit pretty PG).

Jimmy, identifying the pattern, desperately tried to course correct and keep the next round of dates simple. He invited life partner #1 over to watch Love Island. It was casual. Fun. Best of all, free. Only two nights later, life partner #2 asked if he’d seen the latest episode of Love Island. Naturally, Jimmy lied and told her he had not. But Peacock didn’t get the memo. The episode was marked watched in permanent ink.

So Jimmy purchased a second Peacock account.

Another expenditure. This one almost poetic. Jimmy, the generous love bomber, had just found an unpinned grenade in his own living room. His beautiful generosity turned toxic once again.

These past couple of months, without a newsletter to show for, I’ve been thinking a whole lot about Jimmy’s conundrum. I’ve been thinking about how damn hard it is to change. This newsletter, at its best, is arguably without purpose, untamed, and from the mind of a blogger with nothing to lose. But waiting for Jesus to take the wheel often leads to late starts and missed deadlines, leaving me doubting it could ever become a professional pursuit. Could I just write about where I ate breakfast each week? Maybe. Sounds insufferable, though. So just like Jimmy, I might be in a prison of my own indulgence. Valuing most what can also land me in shit.

Then again, at what point does being aware of weakness blind us from the cool side of the pillow? How much change is necessary? I hope Jimmy never becomes cold hearted. I hope to forever write about Samba Alts. Maybe the answer lies in the aggregate. Scott Hatteberg that shit. Regardless, I’m back behind the keyboard and I’ll keep trying my best. So is my good and definitely not toxic friend Jimmy. He might have two Peacock accounts today but one day…he might just be going splitsies on a Disney ESPN Hulu Bundle with his forever partner.

Three Redford Recs

(that aren’t 3 Days of the Condor, Butch Cassidy, or All The President’s Men)

Three Days of the Condor (1975) directed by Sydney Pollack • Reviews, film + cast • Letterboxd — DISCLAIMER: This is 3 Days of the Condor

Spy Game

Redford straight up takes a few Condor fits off the rack but then Pitt says hold my hair bleach…imma put a Tony Gwynn era Padres hat on. Tony Scott adds a couple snap zooms, prints it, and that’s all you need to know about Spy Game.