Nobody loved a party more than Pondo Kosmas.

And if you run a Greek deli, eating and drinking to painful excess is what a party is all about.

The late owner of the Mad Greek Deli on East Burnside Street—he passed away suddenly in February at age 49—ran one of the nation's most insane food challenges for a decade at two locations of his family's deli.

Mad Greek's 10-pound monster sandwich is stuffed with salami, pepperoni, turkey, ham and three kinds of cheese, plus pepperoncinis and a mountain of tomatoes, onions and lettuce. It's all stacked high onto a 24-inch bun and slathered in oil and vinegar, then topped with olives.

Contestants get one hour to polish off the whole thing along with a pound of Greek fries and 32 ounces of their beverage of choice.

The challenge is pretty much impossible, which is why only three people have ever finished it—and two of them were competitive eaters who flew to Portland, lured by a jackpot that grows by $15 every time somebody fails, which is almost always. The last winner, 115-pound Molly Schuyler of Nebraska, left with $600.

The thing about Kosmas' challenge is that it didn't make any sense. The sandwich includes about $65 worth of ingredients—much more than the $30 sandwich costs, even if you lose your bet—all of which the late cook weighed personally and assembled lovingly by hand.

"The only way to understand it is to know Pondo," says Jake Marks, a longtime friend who has helped manage the deli since Kosmas' death. "It was all about family and community. The 20 bucks wasn't the big deal. It was, 'Someone's going to try it again!'"

Pondo Kosmas (Courtesy Mad Greek Deli)
Pondo Kosmas (Courtesy Mad Greek Deli)

But nothing about competitive eating really make sense. That's what I learned from my weeks-long journey through all of the Portland area's meaningful food challenges—that is, the challenges where you don't have to pay if you finish.

In tribute to Kosmas, I took on challenges involving pounds of pho, steaming plates of Cambodian hot wings, and a mammoth hunk of steak that a previous generation of my family attempted to eat.

I learned what it is like to be a python—stretching my stomach to imbibe many meals' worth of food in a single sitting and then slowly digesting it over the course of days. And I did it at personal peril not only to my health, but to my bank account (see below).

My first stop was Mad Greek Deli—the first time someone attempted to eat the 10-pound sandwich since Kosmas' death.

"It was the first time we got together as a group to do it for him," Marks says. "It was emotional for all of us. Because he was that guy. What we do here is a labor of love. It's something that will always be very near and dear to us forever."

The Food Challenge Rules:

When we embarked on this project, my kindly editors worried I might not be properly incentivized to finish each food challenge.

It seems they'd seen far too many videos of news reporters at eating contests gently putting down their forks, pinkies up, saying, "Oh, my goodness!" at the sight of so much food.

So we came to an agreement. I would put my own money on the line.

The total cost of all these food challenges, before tips, was $221.10.

No matter what—whether I won or lost—the newspaper would reimburse me precisely half that amount.

That means if I won all the challenges, I had a chance of making a cool $110.55 bonus. And if I lost every one, I would be out over $100.

Thanks to the generosity of Mad Greek Deli's Jake Marks, who would not let me pay for the first 10-pound sandwich challenge since the death of deli owner Pondo Kosmas, I ended up $7.45 ahead.

The Mad Greek Deli Challenge

March 17, at 7:30 pm

MadGreekDeliprogressivehcallenge_EmilyJoanGreene

The challenge: Eat a 10-pound sandwich stuffed with meat and cheese, plus a pound of Greek fries and 32 ounces of any drink, in one hour.

The stakes: If I lose, I pay $30. If I win, I get the sandwich free, plus an insane jackpot of $750. Each time someone loses, $15 goes into a kitty. Many, many people have lost.

"You're gonna get the meat sweats," says Kevin, a regular customer at Mad Greek Deli. He thinks about it for a second, then reconsiders. "You're gonna get the meat and cheese sweats."

He seems unendingly happy about this.

Together we are watching Mad Greek's Ahmet Çelik, who's in the kitchen building my ruined future.

He is pulling, slicing and carefully weighing the ingredients for a 2-foot-long, 6-inch-tall layer cake of cheese and cold cuts. Each sledge of provolone, Swiss and cheddar is the width of a quarter-pound cheese package at the supermarket. In between them are literal pounds of meat.

The sandwich, taken together with fries and drink, is over 13 pounds—the weight of the heaviest baby ever born in India.

And I'm supposed to eat it all in under an hour.

"Hope you've gone to the bathroom," Marks says, "because once your butt hits that seat, you can't lift it again."

I have engineered a strategy. I will take ketchup with the fries, because it's more watery. I'll only drink water, not the soda I was offered. And I will eat the bread and mountainous pile of lettuce last, on the reasoning that lettuce will be easy to swallow and the bread might otherwise expand in my stomach.

But all that strategy is the work of a fool.

After 10 minutes and maybe a pound and a half of food, I know that I'm doomed not merely to fail, but to experience a form of misery that is entirely new.

I would love this sandwich in small doses—an old-school, deli-style sub with a Greek twist from a spot where most ingredients are housemade. But in such volume, the salt of multiple pounds of salami and pepperoni and cheese have colluded to suck the water out of all cells in my mouth. I no longer taste the sandwich. What I have instead is a feeling I remember from my distant past—slow-building pain and exhaustion that I know is going to continue for 50 minutes.

The feeling is…high-school athletics.

This exertion of solemn and determined will in the face of intensifying suffering is familiar to me only from long-distance running and the sticky tortures of wrestling. This sandwich is a deoxygenating lung, an arm around my neck squeezing the life out of me.

I continue, bite by painful bite, as the time ticks forward. Thirty minutes left, 20, 10. I will not win. But I will eat half of this sandwich. Because if I can get through half, I have hopes of winning somewhere else—the other challenges require that I ingest only 5 pounds of food.

There are at least 30 people watching me fail. For the final 10 minutes, I think I just chewed a single bite of food. But as they count down the final seconds, the people in attendance at Mad Greek cheer loudly and, it seems, sincerely. Couples stop by afterward to survey the carnage or taste-test the sandwich. Marks declares me "a champion in my books."

This is why people like Greek weddings.

"This is the first challenge since Pondo died," says Mad Greek manager Nicole Hoff, who's worked there 11 years. Tears well up as she tells me. A memorial to Kosmas sits by the front door, with photos of his beefy arm around the shoulders of everyone I've met today. "This is the first one we've made without him."

No matter how many times I insist, Marks refuses to let me pay, slapping $40 on the table.

"You're lucky the T-shirts for losers are on order," Hoff says.

Result: Failure. But the remaining half of the sandwich is lunch for our entire office.

Health effects: When I leave, I feel drunk, though I am very sober. There is no blood anywhere near my brain, and even the five-block drive home feels dangerous. My stomach does not quite hurt—but it is angry enough I wake up almost every hour during the night. I eat no food until 10 pm the next day.

The Tex-Ass Doughnut at Voodoo Doughnut

March 21, at 9 am

(Henry Cromett)
(Henry Cromett)

The challenge: Eat a half-pound, 5-inch glazed doughnut that's the equivalent of about six doughnuts in under 80 seconds.

The stakes: $4.50 and a button.

My first attempts to visit Voodoo Doughnut don't really work out.

After three failed tries to avoid lines at off hours—apparently there was a David Bowie tribute— I end up at the eastside location at 9 am on a Monday. When I say I want to take the challenge, the girl behind the counter asks what city I'm from. When I say Portland, she looks amused.

"Matthew from Portland!" she announces, while ringing a bell kept behind the counter for this very purpose. Maybe one person looks up, confused.

I have been given advice on how to complete this challenge, by a man who calls himself Max Carnage—he's completed almost every eating challenge near Portland that isn't the Mad Greek.

voodoo doughnut

But though he has told me to ball up pieces of doughnut and dunk them, in the heat of eating I forget. I dunk doughnut bits without smushing them, and my mouth bogs down with dense and chewy dough. I can't stop laughing as the time runs out.

When time is called, the room makes the approximate sound of a party balloon going flaccid.

"I've never seen anyone win, and I've been here a year," says the girl who rang my bell. Another employee, a veteran, has seen four people succeed "out of maybe 50 or 60."

These statistics are heartening. But I still feel I should have eaten the hell out of that doughnut.

Result: Failure.

Health effects: None more lasting than shame.

“Crazy Wings” at Mekong Bistro

March 21, at 7:30 pm

crazywings_mekongbistro

The challenge: Eat 25 "crazy hot" Cambodian-spiced chicken wings dripping in bird's eye pepper sauce and coated in seeds in 15 minutes.

The stakes: $10 and a T-shirt.

At Portland's only remaining Cambodian restaurant, a tucked-away Northeast 82nd Avenue eatery that doubles as a sports bar, I dive into a bowl of steaming crazy wings far too soon. They are too hot to eat—in temperature, not spice.

But you know what? It doesn't matter.

The crazy wings at Mekong are simply sweet-hot fish-sauce wings with balanced spice, pretty much how I'd order them if I was eating for pleasure. The bird's eye pepper heat doesn't linger or build and punish like, say, habanero or ghost pepper.

There are special techniques I've learned for eating wings, both from the internet and local big eater Max Carnage: The "typewriter," the "meat umbrella," the "bone splitter." I don't do any of them. What I do is I eat the wings, one by one, until they're gone, with 26 seconds to go.

My lips sting. My fingers sting at their cuticles. And for the first time, I am a winner. Frankly, even if I'd lost, $10 is a hell of a deal on 25 wings.

"Next time?" says Mekong's server. "Ostrich wings."

Result: Success! I am now the proud owner of a Mekong Bistro T-shirt.

Health effects: Oh. God. It begins at 4 am, when I wake up feeling that parts of me have liquefied. Capsaicin has accumulated within me in such bulk it has transformed my body into an acid kettle. It is like giving birth to a school of angry piranhas, one by one.

The Pho Challenge at Pho Tango

March 23 at 2 pm

Phoillustration_EliseEnglert

The challenge: Eat 2 pounds of noodles and 2 pounds of meat, served in a bowl of pho broth you don't have to drink, in one hour.

The stakes: $29.95 and a picture on the wall.

Pho Tango is a somewhat nondescript mini-mall Hillsboro pho spot with one highly distinctive feature: a gigantic bowl of pho.

When it arrives, the bowl is massive—but the second I see the plate under it, I know what I'm going to do. I pull out all the noodles and beef, slopping them onto the plate in hopes much of the water will evaporate. I eat all the beef immediately, while I can still swallow.

Over time, the noodles dry into a sort of glutinous paste. It is the most tedious meal I've ever eaten—a plate of slowly drying, sticky rice, mildly sweetened with whatever pho broth remains within it, eaten over what seems like an eternity.

I'm done with eight minutes to spare.

When done, I'm left feeling like the kid at a soccer game who doesn't have a mother. We try steadfastly to get the staff's attention. "I finished! I'm done! I did it! Look, ma!"

Eventually our server almost wordlessly wanders over with a camera and a little flag that reads "I DID IT!" and takes my picture. There is no T-shirt. Still, I leave a winner, swollen with rice.

Result: Winner!

Health effects: The simple starches in this challenge make it the easiest to digest. After less than 24 hours, I feel almost human.

Supreme Pizza at Flying Pie Pizzeria

March 25 at 1 pm

supremepizza

The challenge: Eat a 16-inch, approximately 6-pound pizza loaded with meat in one hour.

The stakes: $29.60, the regular price of a 16-inch pizza.

I am afraid of this challenge for a personal reason: Flying Pie's pizza and I go way back, and I do not want to associate this pizza with pain.

At a normal pizzeria, eating a 16-inch pizza would not be difficult. But Flying Pie's slices are so monstrous that a single lunchtime slice will gorge most diners. The dough is finger-thick, the cheese dripping, the sausage a burial mound for multiple pigs. And as with the Mad Greek Deli sandwich, there is enough salt on this thing to mess up a horse.

After 20 minutes, I feel an ever-building pressure against my tonsils as my body ceases to understand the pizza as food and begins to think of it as a toxic assault. Everything slows down.

At Mad Greek, there were cheers; at Pho Tango, there was apathy. Here at the Montavilla Flying Pie, the prevailing mood is that I'm not too bright.

"He ain't gonna make it," says a man in a cowboy hat, who taps me on the shoulder as he leaves.

"Pain is temporary," says a nearby dad.

I died on the final slice, with probably an additional half-pound of stray meat on the platter. The fine people of Flying Pie, in generous condolences, send me out with a T-shirt anyway.

Result: Failure and pain.

Health effects: In what amounts to an egregious tactical error, I visit a beer festival thereafter, reasoning that a few samples couldn't hurt me. I am wrong. I am like an ancient Hebrew caught at adultery, whose punishment is death by stomach rupture as grain expands within. Once I finally reach a chair, I do not move or think or speak for over two hours.

Giant Calzone at Opa Pizzaria

March 28 at 7 pm

calzone

The challenge: Eat a 5-pound calzone in 30 minutes.

The stakes: $27.

The spelling of "Pizzaria" lets you know there's something different going on here: This is a Greek pizzeria, and so the fillings in the calzones are equally Greek. There is gyro meat on pizzas.

The food challenge is sort of a choose-your-own adventure. The massive shell of the calzone is the same, but what's inside the dough is chosen by the eater, with eight options.

I opt for vegetarian. I am becoming, slowly, afraid of meat.

Opa limits winners of its challenge to one attempt a year. "There are people who could do this once a week for a free meal," says our server. "We had to set limits."

On the photo board of winners, the same few people show up again and again. "This lady ate a 7-pound calzone," the server says.

Kindly, the staff allows you to cut apart the calzone and let it cool so you don't singe your mouth. Unkindly, they give you only 30 minutes to eat 5 pounds of thick-ass crust, sauce, cheese, olives, and pepperoncini.

I cut it into itty-bitty pieces, and it's pretty much room temperature by the time we start the egg timers.

The olives and peppers take their sodium toll, and the dough feels unswallowable after the first 15 minutes, but I get painfully close before the challenge ends. There's about a lunch slice of pizza left when I'm done. I'm maybe a half-pound shy.

Screen Shot 2016-04-05 at 4.22.10 PM

The proximity to victory is…painful.

Result: Close is no cigar. But I walked out with a T-shirt. "It doesn't say winner," says the server. "And it doesn't say loser."

Health effects: Am I getting used to this? I'm…eerily fine. My body has become accustomed to this bizarre rhythm of bingeing and fasting. But the next day, two angry zits appear on my face. I am unhealthy. And I am starting to measure all food in pounds.

GoGo Burgers at GoGo Burgers

March 31 at 6 pm

(Rachael Renee Levasseur)
(Rachael Renee Levasseur)

The challenge: Eat two gigantic, towering four-patty burgers, plus 2 pounds of french fries, in an hour.

The stakes: $40.

Somehow I never knew this place existed. Gogo is a Vietnamese burger shop in Aloha that also serves pho, and used to be a Mongolian grill. It now makes stacked multi-patty burgers and offers a giant condiment bar.

"You go for it!" shouts a man from the kitchen as I pile into the foot-tall burgers, each stacked with four half-pound beef patties and much, much bacon, lettuce, tomato and onion. Even sauceless, the burgers are pretty damn nice. And I get through them both in about 40 minutes.

The fries, though, are trouble.

By the time I get to the fries, they are 2 pounds of cold, salty and oily mass that offers little incentive to continue. The mush accumulates in my cheeks, refusing to pass the gullet.

For the first time, I raise the white flag, with nine minutes and a pound of fries to go.

(Rachael Renee Levasseur)
(Rachael Renee Levasseur)

At Gogo, the hourlong eating challenge reveals its fundamental human character: loneliness. It makes me feel so lonely to eat like this, wrapped up in a titanic struggle whose point could never be expressed to anyone. Around me there is normal life, normal conversation—marriage, jobs, family.

And here I am, as depressed as I'd ever been…chewing potato.

Result: Failure is becoming the new normal. Also, I am losing so much money. Think of the wonderful meal I could have had for $40 somewhere else.

Health effects: This is just the new me, walking around with a food baby, retaining so much water you'd swear I was actually pregnant.

The Steak at Sayler’s Old Country Kitchen

SaylersSteakhouse_steak_RachaelReneeLevasseur

April 2 at 1 pm

The challenge: Eat a 72-ounce steak, plus all the trimmings, in one hour.

The stakes: $65 and a T-shirt.

The Mad Greek Deli's challenge may be the most insane in town. But the one at Sayler's Old Country Kitchen is the most famous.

Since 1948, this hulking East Portland steakhouse—it looks like the lobby of a Red Lion—has offered a free meal to anyone eating an uninterrupted 4½ pounds of boneless, no-trim beef, accompanied by a nonsensical array of sides: two each of pickles, olives, carrots and celery, a piece of bread, 10 french fries, an onion ring, and a little bowl of ice cream.

The challenge is a chance to avenge my Uncle Rick, who attempted to eat the steak in 1973 when he visited Portland for the East-West Oregon Shrine All-Star football game. He made it through only two-thirds; the Shriners picked up the tab.

I'm allowed to eat the salad early—probably a means of tiding me over because it takes almost an hour to cook a 72-ounce steak medium rare. Next to me is a man eating a 40-ounce steak he says lasts him three meals. He wishes me good luck.

(Rachael Renee Levasseur)
(Rachael Renee Levasseur)

But you know what? I may struggle with bread, chewing endlessly, and I may give up in the face of french fries. But meat is meat, and I like it. Some primal, pre-civilization impulse keeps me chewing. After trimming around the hard-to-swallow well-done bits on the outside, when I am down to about 24 ounces of mostly red meat, I know that I have won.

Upon downing my mostly melted bowl of ice cream and cleaning up the weird parts for good measure—with two minutes to spare—I finally understand why anyone would undergo the pain of an eating challenge. It is an enormously satisfying accomplishment, if also egregiously wasteful in ways I should probably recognize.

Along with a T-shirt proclaiming "I ate the WHOLE Thing," I receive two little white numbers with adhesive on the back.

(Rachael Renee Levasseur)
(Rachael Renee Levasseur)

On the big board that greets all visitors to Sayler's, I change the number of men who have succeeded in eating the steak from 639 to 640—satisfied in the knowledge that I had won, and that I would never have to do anything like that ever again.

Result: Success, sweet success, and family pride.

Health effects: A sense of well-being doctors could never find in their fancy charts.

Portland-area challenges that no longer exist or don’t offer free meals.

Balls of Fire at Salvador Molly's

These habanero hush puppies are a mouthful of hot glass on the way in, and an amusement-park version of Crohn's disease on the way out. If you eat them, you get nothing but pride and a picture on the wall.

Diablo Burrito at Allan's Authentic Mexican Restaurant

Once upon a time, this spicy burrito was free if you ate it in 10 minutes. Now you get free burritos for a year, but only if you beat some nutty record set by a woman from Nebraska.

The Behemoth Burger at the Ram

The Behemoth contains Anaheim peppers, American cheese, cheddar cheese, horseradish-chive havarti cheese, caramelized onions, lettuce, pickle chips, mushrooms, bacon, ham, corned beef and tomato. It costs $25. There is no reason to eat it—it costs more than the T-shirt you get for enduring it.

El Jefe Wings at Fire on the Mountain

These habanero chicken wings are a mouthful of hot glass on the way in, and an amusement-park version of Crohn's disease on the way out. If you eat them, you get nothing but a shirt and a picture on the wall.

Five-Pound Poutine at the Original Dinerant

The challenge has been discontinued. You could probably still order 5 pounds of gravy fries and eat them for an hour. But I don't know why you would, and you don't get anything if you do.

The Marine at Killer Burger

This serrano-habanero-ghost-pepper burger is off the menu. It hurt people. People threw up. Their faces swolled up. It burned fingers. It was the only Killer Burger burger that might actually kill people. Some things are too damn hot to eat, and this was one of them.