Sometimes Old Broke Players Beat The Odds…Believe It Or Not!

In case you’re new to this site
I’m the Gloomy Boomer and this is my blog. I’ve been blogging now for several years. Maybe three, maybe four years. I don’t remember, exactly. I loose tract of time. A while back, I got depressed and deleted all my posts, the good ones along with the shitty ones. I don’t know why I did that. I get depressed. I keep forgetting stuff. I’m seventy three, I remember that much.
I live on my boat in a marina in Sausalito. Here’s my dock.

Here’s a boat I used to own. Called Scruffy.

Here’s another boat I used to own. Unnamed.

Both of these former boats of mine are still here on C dock just a stone’s throw from my current boat.

The Double Lotus. That means real lucky.
I’ve owned a half dozen old boats. My current boat is my favorite. I used to do a lot of sailing. Nowadays I just sit on my boat. Funny, though. The Double Lotus is the most sea worthy of all the boats I’ve owned. Why don’t I take it out? Maybe the reason I don’t take it out is simply that I myself am no longer sea worthy. But that’s okay! I’m not feeling sorry for myself. I’m perfectly happy to just sit on my ass aboard The Double Lotus. Right here on C Dock. I mean it. This is a nice comfortable little port in the storm.
Wine Delights
Here’s a shot of me at my Booze Sample Job.

I hand out free booze samples to Safeway shoppers. It’s not the job I expected to have as this stage of my life. It’s not a job I expected to have at any stage of my life. It’s not even a job. I don’t work for Safeway. The Safeway manager knows I work for this company called Wine Delights. Beyond that she leaves me alone and couldn’t care less if I show up or not. I buy the booze I serve at my table at the Safeway store, then get reimbursed weekly by Wine Delights. I show up and set up my table. Nobody from Wine Delights has ever stopped by to check up on me to make sure I showed up. I take pictures of myself handing out samples, then upload the photos onto a Wine Delights portal and fill out an invoice. I take a picture of the receipt for my booze purchases and upload that onto the portal invoice. The receipt shows the time I made the purchase. That’s how they know I showed up on time. What they don’t know is whether or not I worked the full four hour shift. I simply pretend I did. Usually I work at least three hours, mainly from fear that somebody from Wine Delights might actually show up. Nobody has ever shown up. Once a week they deposit money in my bank account. Not much, but enough. And I can keep the left-over booze. It’s like I’m working for imaginary bosses but getting paid in real money.
And yet, the job is real…believe it or not!
A depression tonic
I’ve worked for Wine Delights for several years now. Three, maybe four years. I don’t remember, exactly. The Wine Delights portal will tell me exactly how long I’ve worked at this job. I’m not going to check it now because…because it would just make me depressed. Better for me if I just keep writing. Writing is my depression tonic. If I decide to delete this blog post, it must mean the tonic is not working. On the other hand, if I delete this blog post and start another post, that might mean the tonic is still working…unless I keep deleting posts.
If you’re reading this post, the tonic is working!
My booze sample job is part time. The way I get shifts, I tell the portal when I’m available to work. The Portal then schedules my days and I’m expected to show up. Lately I’ve been working only one or two days a week. I could work more If I pleased, but I keep telling myself I need to find another gig. Do something other than hand out free booze samples. Something that pays more. Start a business selling something. Get creative with my work life. Thinking about my work life is depressing. What I need is a scam. A legal heist. A deal that will net me a big wad of cash.

In a nutshell, what I need to do is find a way to beat the odds. And yet, I’m working a job that’s not really a job and I’m getting paid for it. That’s kind of like beating the odds, don’t you think?
The depression tonic is kicking in!
I’m worth almost nothing and yet I live quite comfortably here in Sausalito. One of the most beautiful spots on the planet.
I can stand on the deck of the Double Lotus and look around and see nothing but beauty.

Angel Island…

Belvedere on the horizon…

The coast trail…

Mount Tam…
It’s days like this when I feel like I’m beating the odds!
Norm
I call Norm every day or so. Mainly to see how he’s doing. Make sure he’s not out on the street. Or if he is out on the street see if maybe there something I can do for him. I mean, I aint gonna put him up. I might put him up for a day or so, then he’ll need to go sleep in his car or something. Norm is 76 years old. Least I think he is. He was born in 1950. So, yeah, he’s 76 years old. Norm is one of the few people I know who’s less well off than I am. Financially speaking. Attitude-wise, he’s way better off than me. More well adjusted to his lot in life. Less prone to depression. Norm possesses Joie de vivre. I don’t. So I guess Norm is way better off than me, philosophically speaking.
Here’s a shot of Norm.

Like I say, I call him every day or so just to check up on him, make sure he’s still afloat. Norm lives on a 29 foot Cal Sailboat parked at the San Rafael City Marina, a section 8 haven for deadbeat boaters and illegal-alien liveaboards. Here’s a little taste of Norm’s dock.

Norm was a year behind on his rent and facing eviction when I came thru for him. More or less. I helped him get a job with Wine Delights. He started work for the company and before long he was the star performer. Earning bonuses every damned week and making me look like a schmuck. Soon he was getting offered shifts that would normally go to me, making me feel like a putz for ever sticking my neck out to help bring him on board. Well, in those days I wanted to work, so it mattered to me. Now that I’m working one or two days a week he can have all my shifts he wants. Fine by me. But what happened, Norm sprained his ankle and ran to the hospital like he always does at the drop of a hat. The doctor said he could apply for workman’s comp. So that’s what he did. He got a note from his doctor saying he can’t work cuz of the sprained ankle (which wasn’t really sprained, he just thought it was) and he promptly stopped taking shifts thinking he’d apply for workman’s comp. Good for him, I’m thinking. I mean, why work when you can get free money? But what Norm didn’t take into consideration was the nature of Wine Delights. They aint a real company. They’re an Internet Gig. When you apply for Workman’s Comp. you gotta have some sort of communication with real people who run a real company. Wine Delights just stalled him. Six weeks now they been stalling him. Meanwhile Norm has run through his savings. I don’t know how he’s getting by. Then I found out, cuz he told me. He steals. Everyday he goes out and steals. That is to say, he shoplifts. Which is stealing. So now, when I call up Norm to see how he’s doing, the first thing I ask is:
“Did you steal today?”
“Oh, yeah.”
“What did you steal?”
“Let’s see. I grabbed some Sand Dabs, some fresh jumbo shrimp, and the good olive bread from Whole Foods. Then, at Goodman’s Hardware, I picked up a water hose and a new space heater.”
“No shit. Just like that?”
“Just like that, baby!”
“And you go out everyday and steal something.”
“Oh, yeah.”
“Wow…that means you never pay for food.”
“Never.”
“Why don’t I do that?”
“I’m telling you, man. You oughta.”
“And you never worry about getting caught?”
“Never.”
“Never?”
“Never. I used to go into a store and grab something to buy and then stick something to steal in my coat, then go through the check stand. Now what I do, I load up a cart and just walk out. I don’t buy anything.”
“Just like that, you walk out.”
“Just like that, baby.”
“Why don’t I do that!”
“You really oughta.”
“I could save hundreds of bucks a month on food.”
“Thousands.”
“Jesus Christ, what’s the matter with me?”
“You’re afraid of getting caught. That’s why most people don’t steal.”
Maybe he’s right. Forget the morality of it. I used to steal, back when I was a kid. Then I got caught.
“Did they chase you?”
“Yeah. A checker chased me down the street and grabbed me.”
“They don’t do that anymore.”
“No?”
“Liability issues.”
“Damn! Why don’t I start stealing?”
“You really oughta.”
“Every day I could go out and steal my meals.”
“Every single day.”
Well, old Norm’s been stealing every day now for the last six weeks. My admiration for him has grown exponentially. He’s beating the odds! Maybe I should start stealing. It sure would help me, financially. Something tells me the odds of making a clean get-away would not be in my favor..

Lester
Today’s Wednesday. Sooner or later I’ll get a call. For sure by the end of the week. Lester, the poet, calls me once a week. He calls with a request for a thirty can case of Coors, delivered to his house, in exchange for which I’ll receive in the form of reimbursement a check for twenty five dollars, although the price of the beer is $26.51.
I’m not gonna quibble over the dollar fifty one.

But it’s a pain in the ass, cashing his checks. My bank, BMO, has one ready teller in all of Marin County. So I gotta drive to Larkspur to deposit the check. Last time I delivered his beer I told him as much. I said,
“Listen Lester. Cashing your checks is a pain in the ass. I’m not a caring person. I realize you’re in bad shape. But I got better things to do than do your beer runs. You need to get real professional help!”
He gives me a blank look. He says, “I won’t ask you anymore.”
“Call Door Dash. They’ll deliver your beer.”
“They’ll charge me 25 dollars delivery fee.”
“That much?”
I don’t know if they charge him that much. Certainly they’ll want something. Lester lives on about a grand a month Social Security. Maybe a bit less. Not much more than me. His girlfriend, Sherry, died in bed last spring. He wont sleep in the bed. He avoids the bedroom. Then he tripped and injured his hip. He won’t go to the hospital. He’s been squatting on the living room sofa, waiting to die. Damn! I’m starting to feel sorry for him again. He’s not gonna die anytime soon. I mean, sooner or later he’s gonna die. But my thinking is he’ll beat the odds and live for a long ass got damned time yet. Drinking the beer I bring him. Beating the Odds!
“Okay, listen,” I tell him. “I’ll do you another beer run. But only if you call the V.A. and get some help. You’re an Ex-Marine. Call the V.A…Understand?”
“I’ll do it,” he says. “I’ll have Martin drive me to the V.A. on Monday.”
Martin is Sherry’s son.
Martin owns the house now.
The same house where Lester sits on the sofa and drinks the beer I deliver…
Lester lived with Sherry for seventeen years. Lived with her in her house for many years while Martin came of age, moved out eventually, married a nice Chinese American girl, moved with his bride into a house of their own in Fremont, where he’s closer to his well-paying Silicon Valley Tech job. Then, last Spring, Sherry dies in bed without leaving a will. Martin inherited the house. Lester got nothing. Martin is a nice kid. I call him a kid although he’s 32 years old. Martin’s new mother-in-law is a different story. She’s been pressuring Martin to boot Lester out onto the street. Lester has no legal claim to the property. Lester has nowhere to go. He’s got no car he can sleep in. All he’s got are the cloths on his back and ten thousand books, stored in boxes in the garage. He’s hobbling around on bare feet and a filthy bathrobe. Meanwhile the house is a shambles. Damn! I’m starting to feel sorry for him again.

Beatrice
I gotta stop off at Target in Marin City and pick up this god damn 30 can case of Coors beer which weighs a ton. All I really want to do is kick back on my boat. Try and forget I’m 73 years old with a pack of broke player friends…Try and forget I’m a broke player myself….try and forget I’m the pot calling the kettle black…
But first I gotta meet Beatrice at the Clipper Marina Parking lot, where she sometimes camps out. Beatrice is my ex-girlfriend from almost twenty years ago. She’s currently living in her car. We’ve remained friends although we don’t get along. We see eye to eye but we don’t like each other very much. I’m still her friend, she’s still my friend. What’re you gonna do?

I pull in next to her and get out. The little dog, Bali, is jumping around like crazy, eager to be petted.
Beatrice glares at me. “Took you long enough.”
I hand her a twenty. “You need another twenty?” I got one more twenty in my wallet. I don’t want to give her my last twenty. Why did I ask her if she needs another twenty?
“That would help,” she says.
I don’t want to ask her why she’s broke only a week after she got her social security check. She gets a hefty check every month. Hers plus her dead ex-husband’s social security. She snagged that after he died in the Maui fire. I mean, it sounds morbid but nothing I wouldn’t have done. My point here is she could rent a room if she found a place outside of Marin County. But she won’t leave Sausalito. Meanwhile her respectable friends shun her. Including her sisters, who are all of them well off living in fabulous homes. A lot of the reason they shun her is because Beatrice carries a sharp blade and will cut you without batting an eye. She’s put down the best of them. Now she’s all alone. Just her and Bali. Well…there’s me. But I’m only ever good for a twenty when she’s desperate and rolling on fumes. Sometimes I’m good for forty.
“I hand her my other twenty.”
“Thanks, Gloomy.”
She fires up her car.
“Listen Beatrice. I was thinking of something.”
“For a change?”
“Listen…you know my friend Lester.”
“Isn’t he one of your Boat Hobos?”
“I got him a job with Wine Delights. He did real well until he hurt his ankle. So now he’s not working.”
“Why am I not surprised…”
“No, no, no…he’s doing real well, not working. He goes out every day and shoplifts. All his food he steals. Other stuff he needs he steals. He never gets caught. He says because he’s old and respectable looking he can get away with it. He just walks out of the store like it’s no big deal. I’m telling you, they don’t chase after shoplifters anymore. They got liability issues.. Lester’s been stealing every day now for six weeks.”
“Am I supposed to be impressed by that?”
“Honestly Beatrice, you should do that. You could go out and steal every day and hell you’d have enough every month to rent a nice place for yourself. Think about it.”
She takes the dog into her arms. “I have Bali to consider. My luck I would sit in a jail cell and Bali would be euthanized. And I would have you to thank for the bright idea…”
I’m watching her pull away. Wondering how much longer her luck’s gonna hold out. She’s been on a list of beneficiaries of the Maui fire…4 billion dollars in awards directed to 21 thousand people…she managed to get herself on the list as a family member of a victim. They’ve been stringing her along. Maybe it’ll happen for her. I doubt it. But if it does, she’ll be a millionaire.
That would mean she beat the odds better than anybody I know.
Rest in Peace, Sherry
I get back to Lester’s place. I mean Sherry’s former place. I sit for a moment before hauling out and lugging the 30 can case of Coors up the short flight of stairs to Lester’s squalid living room. I stare at the vintage toyota parked in the drive, with the stuffed animals perched on the back seat. Car hasn’t moved since Sherry died. The tires are very low. I wonder if it starts. Probably. It’s a Toyota. It was Sherry’s car. Lester shuns the car. Just as he shuns the bedroom where she died. He used to drive the car all over hell. Kinda funny with those toy animals in the back. She got tired of him driving her car all over hell finally and took back the keys. Leaving him to walk to the gym. He used to do a lot of walking. He stayed in shape.

During Covid I talked Lester into signing up for the free unemployment money, which netted him 14 grand in one lump sum. Those were the good days for broke players. I told him then, “this is your opportunity, Lester. You have the money to buy a nice car. Something big enough to sleep in. A nice RV or maybe even a boat. You can be independent now. You can be free of Sherry!” Did he take my advice? Hell no. He used the money to pay off his credit cards.
What else is there to say?
Rest in Peace, Sherry…
Stay Positive Today!
I’m banging on the door.
“It’s open,” he shouts. “Come on up!”
I lug the 30 can case up the short flight of stairs, past the little sign on the wall that says STAY POSITIVE TODAY! A sign Sherry hung there years ago. I plop the case down on the kitchen table. Lester’s in his usual spot on the grubby sofa. His bathrobe open to his naked body. I’m trying my best not to look at him.
“Your check’s on the counter,” he says.
I shove the check in my wallet.
“Hand me a beer, would you? And take one for yourself.”
I always decline a beer for myself. One less beer for him means I’ll need to do another beer run sooner rather than later. I got nothing to say. He’s staring at the television screen…and I’m thinking…what is there to say except Stay Positive today!
I’m headed toward the landing when he turns to me suddenly and says, “By the way, Gloomy. I got some good news.”
“You do?”
“Yeah. Martin says he’s not going to evict me. He says I can live here until I die.”
“That’s…incredible news!”
He nods. “Listen,” he says. “Maybe next time you come. Instead of beer, maybe could you bring me a bottle of Gin? Beefeater is my favorite. A gallon of Gin, plus a quart of Seagram’s Tonic Water. Oh, and one of those plastic bottles shaped like a lime. Could you do that? I’ll gladly pay you by check.”
“I don’t know if they sell those plastic lime bottles anymore.”
“Oh…well in that case bring me a lime I guess. Or maybe four limes…”

I’m headed down the stairs. I pause for a moment at the Stay Positive Today! sign.
I’m thinking Lester found a way to beat the odds after all…
3 thoughts on “Sometimes Old Broke Players Beat The Odds…Believe It Or Not!”
Oh my word Don,
I feel like I just read a chapter out of a Steinbeck novel!
One of my “depression tonics “
is reading my brother‘s blogs, knowing he’s hanging in there another day with his interesting insights on life.
I didn’t know what this phrase meant so I asked AI:
“Joie de vivre” is a French phrase that translates literally to “joy of living”. In English, it means a keen, buoyant delight in being alive, a high-spirited zest for life, or an exuberant enjoyment of everyday moments.
Yes, they still make the plastic lemon bottles.. They are great “go tos” when you are out of real lemons and cheap too. 🍋
PS
PLEASE don’t start stealing
About fucking time. Bonnie is right
Love it! This is what I like to read . Good one. Keep it up.