Chester and Finnigan: A Friendly Haunting
It was my first bar shift. I’d already been working at the hotel for about eight months, but I had finally turned legal age to serve in the bar. The money was better, sure, but that wasn’t why I was excited. I was legal now—no more café waitering for me. No more slinging hash, no more cleaning up after babies while parents ignored them. No more dealing with chronic nitpickers trying to score a free meal by claiming the food “was better last time,” and definitely no more hearing that eraser-smudged phrase, “We always eat here.” Of course they did—because if they bitched loud enough, management would comp the bill.
But that was behind me. From now on, it was bar all the way.
I showed up early for my shift. Not by much, but early enough to prep. I signed out my float, loaded my hip changer with quarters, dimes, and nickels, then zipped around the bar wiping down tables, setting ashtrays, and propping up tent cards for the daily specials. I had taken the bar menu home weeks earlier and practically memorized it. I didn’t think I could be more prepared.
Robert, my bartender, was ready too. He hadn’t said much to me, just busied himself stocking shelves, mixing juices, checking liquor levels, and slicing fruit for garnish. But now we were ready to open, and he stood silently at the till, watching the clock. 10:28 a.m.
Two minutes to go.
It felt like eternity.
The only sound came from the front doors rattling as eager regulars checked to see if we were open yet. Robert took it in stride. Me? I was ready to burst. Finally, he glanced at the clock, then at me, and smiled.
“Open her up,” he said.
Off I went.
Only one person was waiting. A tall, thin, gray-haired man in his sixties.
“Good morning,” I greeted, flashing my over-eager grin.
He didn’t acknowledge me, just darted past and slid into a seat against the center of the far wall. As I approached with tray in hand, I noticed he’d already placed two quarters and two dimes in a perfect row on the table.
“Good morning,” I repeated, in case he hadn’t heard me. “What’ll it be today?”
“Two pints,” he said, then mumbled something that sounded like, “No, I’ve got it,” though I couldn’t be sure. His stern expression told me not to ask. I just nodded and turned toward the bar.
I nearly sprinted.
“Draw two, please,” I said to Robert, plunking my tray down.
Robert grabbed two chilled mugs and opened the tap. “Seventy cents,” he said.
With practiced flair, I flicked the coins from my hip changer like a gunslinger.
I returned triumphantly and set the mugs on the table.
“I don’t want those,” the man snapped. “I want two pints of draught in sleeves, boy. And bring me a chessboard. Finnigan and I want a game. Tell Cupcake up there to quit screwing around and pour my beer properly. He knows those mug handles knock over the chessmen.”
“Cupcake?” I asked.
“Yes, Cupcake. Your bartender. Don’t you know anything, boy? That’s what Finnigan calls him—‘cause he’s sweet on the girls. Sweet as a damn cupcake.”
“Well, it is my first day,” I offered.
He just mumbled something and waved me off.
When I got back to the bar, Robert was already pouring beer into sleeves and grinning like a kid on Christmas.
He took the mugs from me, handed over the proper pints, and kept grinning.
On my way back to the table, I noticed the man was talking to the empty chair across from him. Not just muttering—but arguing.
I slowed my approach, watching. He noticed.
“Hurry it up, boy! We’re getting thirsty!”
We?
That’s when it clicked. He wasn’t just talking to himself—he had an imaginary friend.
Great. My very first customer is a nutcase.
Still, I played along.
“Here’s your two sleeves and your chessboard, sir. That’ll be seventy cents.”
“Money’s on the table, Velvet Head. Just pick it up. I ain’t handing it to you.”
“Very well. And thank you.”
I reached for the coins. “Velvet Head?” I muttered—apparently out loud.
“Yes, Velvet Head,” he said. “Finnigan thinks your short hair looks like black velvet.”
Surprised—and now amused—I turned to the empty chair and said, “Thank you too, Finnigan. My girlfriend says it feels like velvet, too.”
That broke him.
His face softened. He smiled.
“I’m Chester,” he said, extending a nod. “Been coming here a long while. Most folks ignore me. You’re the first polite one I’ve had in ages.”
I thanked him and moved on to other tables, but I kept an eye on him.
He set up the chessboard, made a move, took a sip, then cracked a comment at Finnigan. Then he’d get up, sit in Finnigan’s chair, make a counter move, sip the second pint, and taunt Chester from that seat. His whole demeanor shifted. Back and forth, he went—playing both sides of the board.
I finally asked Robert, “What’s the deal with Chester?”
Robert looked curious. “What’d you say to him? He’s acting tame today.”
I told him everything, including the bit about Finnigan and the velvet comment.
“Strange,” Robert said. “He usually gets nastier with new staff. Never introduces himself.”
“He did today. Even said you’re called Cupcake.”
“That old fart,” Robert chuckled. “He’s got half the staff calling me that now.”
He explained that Chester used to be a prominent lawyer in town. Finnigan was his law partner. Years ago, Chester took his wife, kids, and Finnigan on a trip to see Kakwa Falls in Alberta, It was raining, and while driving his motorhome down a narrow gravel road, a logging truck lost its load while passing. The truck crushed the rear of the RV. Everyone but Chester died instantly. He blamed himself.
Not long after, Chester quit the firm and started coming to the bar every morning—with Finnigan.
Robert added, “You might want to check his table again, Velvet Head. Looks like he wants another round.”
“Okay, Cupcake,” I said with a smirk.
Chester had set two neat piles of coins on the table—one in front of himself, one in front of Finnigan.
“No! I’m buying this round,” he snapped at the empty seat. Then, to me: “Thanks, Velvet Head. Take my money, not his.”
I brought the pints and took only Chester’s coins, leaving Finnigan’s untouched.
Later, I heard a glass slam. Chester stood, stormed out, and I went to clean up. Chester’s pint was empty. Finnigan’s was untouched. The coins had been moved to Chester’s side. The chessboard showed checkmate—in Finnigan’s favor.
Still punishing himself, I thought.
I worked that bar for a couple more years. I moved to nights, but still picked up day shifts. Every morning I worked, Chester was first at the door. Always the same table, same routine. He always argued about who should pay for the second round. Chester always lost the game. Finnigan never touched his second pint. And Chester always stormed out.
But I grew to like him. Even the “Velvet Head” nickname stuck. When I left for a new nightclub job, I heard later that Chester had passed away peacefully in his sleep.
I missed that routine.
Five Years Later…
After five years at the club, I’d made manager. One morning, road construction forced a detour past my old hotel. After making the bank deposit, I decided to stop in.
The bar had changed—new lighting, bigger stage, more dance floor. The old service bar now had seating. I sat down and ordered a pint.
“In a sleeve, please,” I added.
“That’ll be $3.75,” the bartender said.
I handed over a five. “Keep the change.”
“Hey, does Robert still work here?”
The bartender shook his head. “Don’t know any Robert.”
“How about Cupcake?”
He laughed. “Oh! That guy! He moved away about a year ago.”
Then I saw it—a plaque behind the bar. A photo of Chester and Finnigan in their law days. Below it, two pint sleeves with their names engraved. A brass plate read: Friends Forever.
“When’d that go up?” I asked.
“That thing? About four or five years ago. Before my time. Can’t stand it. Gives me the creeps.”
“Why?”
“Because every morning when I open the bar, Chester’s glass is dirty and smells like beer. Finnigan’s is full and cold—with head on it. It’s behind a locked gate. No way to fake it. Gives me the willies.”
“That’s only because Chester still hasn’t forgiven himself,” I said.
“Huh?”
“Long story.”