You Can't Lose Them All

THE FALL OF TROJANOWSKI

Before we get into my stories about the seedy underworld of gambling, here’s a story about how I met my wife. A risky adventure that led to the only real sure thing in my life.

Back in the spring of 1999, my friends were throwing our buddy Donick a bachelor party in Mexico. The plan was to rent a mansion in the hills of Puerto Vallarta. I didn’t drink, so I would watch my pals guzzle tequila all weekend and, at the same time, pray the satellite dish would kick in so I could see the Final Four game between Duke and Michigan State.

I had very little money back then but somehow was able to bid $8,000 on Duke on credit in what is referred to as a “Calcutta pool.” This is where a bunch of people bid on teams and you get money for every round your squad advances in the NCAA tournament. As a result, Coach K’s team reaching the Final Four was a good thing for me.

So a bunch of us flew to Mexico for a weekend of debauchery. Puerto Vallarta is beautiful and the fellas got hammered and I was able to watch a scrambled signal of the game on satellite. Elton Brand dominated and the hated Blue Devils made the finals, which meant I was guaranteed to make money off of money I didn’t have.

Isn’t this a romantic story so far?

An even better call was heading out with the bachelor party later that evening to a local bar called Carlos O’Brian’s (a name we would later bestow on our family mutt).

It was a wonderful scene. A bunch of well-to-do Hollywood dudes buying shots for the rest of the bar, which happened to be made up of mostly attractive women. My friend Daniel was handing out lemon shots; Adam Carolla was getting recognized as the host of his popular MTV show Loveline. My cousin Jimmy was there, and—having given Adam his start in show business—this was an ironic scenario where Adam was getting celebrity love and Jimmy wasn’t. Suddenly, after a solid hour of Jimmy being ignored, a beautiful young woman in a red dress approached him.

Everyone laughs at Jimmy.

She didn’t realize what a back-handed burn she had just delivered. We all had a good laugh about it, and I knew right away that this was the woman I would spend the rest of the evening with. Melissa Trojanowski was on spring break with her friends from Wisconsin. With a name like Trojanowski, there was only about a 170 percent chance she would hail from the Dairy State. After making small talk with her, I found out that Trojanowski was a grad student at Madison staying with her two friends in a Hyatt in the heart of Puerto Vallarta. I barely got this information out of her before my friend Daniel announced that he was rounding up several groups from the bar to come party with us back at the house. In a master stroke of debauchery, Daniel lined up a bunch of cabs, loaded groups of women into them, and shifted the festivities to the rented mansion.

Trojanowski and I continued our conversation there and even played tennis on the mansion’s outdoor court. I didn’t let her win, mainly because I’m a competitive idiot, but she didn’t seem to mind and, in fact, apologized for hitting the ball into the net for most of the match.

I liked her more and more as the evening went on and even managed to sneak a kiss in when no one was looking. Eventually, Trojanowski and her friends left and that, I felt, was that.

Jimmy and my buddies were annoyed with me.

“How did you not get Trojanowski’s phone number?”

“You finally meet a woman who is not repulsed by you and you just let her go?”

The way I saw it, I lived in California, she lived in Wisconsin. I had just had a miserable time wrapping up a long-distance relationship and didn’t have the stamina to start up another one. I’d be satisfied getting to first base with a nice lady every few years in a foreign country.

Fortunately, us not being meant to be wasn’t meant to be.

A couple months later my friend Matt Silverstein, one of the Man Show writers, was getting married in Chicago.

That’s when my good pal Tony approached me with the bet.

“If I find her phone number, will you take her to the wedding?”

Seemed like not a lot of downside to this bet, so I agreed.

All we knew was Trojanowski’s last name and the fact that she attended grad school at Madison. The Internet was fairly new, so without Facebook or Instagram this was going to be a wild-badger chase.

Somehow, Tony got in touch with the university and used his magic powers to convince the bursar, or whoever, to give him the phone number. That number was then placed on my desk about twenty minutes after the “bet” was made.

Milwaukee was a cheese block’s throw from Chicago, so this could actually happen. I called Trojanowski and told her that I wasn’t stalking her—always a solid way to begin a conversation—and invited her to the wedding, which was a few weeks away. She seemed weirded out and said she’d get back to me later in the week.

I figured I was a 7/1 long shot at this point. This bet was one well-timed excuse away from being bust. Anything would’ve worked. The smart money was on “Sorry, I forgot my uncle Ray is playing lead accordion at the local polka festival that night.”

Much to my surprise, Trojanowski didn’t wait a few days but actually called back in a few hours. “I would love to go to the wedding” was not what I was expecting. I was stunned.

So we went to the wedding, had a great time, and proceeded to alternate flying to each other’s hometowns one weekend a month for a year until she graduated with a master’s in social work and agreed to settle down with me in my cousin Jimmy’s basement. (I know: How?… Why?)

Melissa Trojanowski was everything I could want in a wife and more. I popped the question and she agreed to walk down the aisle to the Fox NFL Sunday theme song.

She knew that gambling and my love for sports were a tremendous part of my life. We honeymooned in Kauai where every morning I’d run downstairs to the business center of the hotel to check on Asian soccer scores. I had a theory that I would profit if I parlayed seven or eight big favorites together to get even money. Yup, this on my honeymoon. The theory, by the way, proved to be faulty.

Now, that kind of behavior would’ve urged almost any other woman to seek an annulment. Not Trojanowski. She took everything in stride.

A couple years after my Asian soccer parlay phase—which ended up being a losing proposition, believe it or not—we planned on having our first child. Anyone who’s been through this knows there can be a lot of preparation involved. The mother-to-be has to figure out when she’s ovulating. She has to pee on a stick to see if she’s pregnant. In solidarity, I would also pee on a stick, by the shed in the backyard. I figured either we were in this together or we weren’t.

We were in full baby-making mode in the fall of 2004. At the same time I was starring in hidden camera comedy bits for Jimmy Kimmel Live! We’d shoot these in Las Vegas, because, at the time, the state of Nevada deemed it legal if one party had knowledge of the recordings. Another reason Nevada is the greatest state in the universe.

We would typically camp out at my friend Ken’s house and screw with delivery people. It was an absolute blast. Didn’t seem like work at all. We made people set up bouncy houses in the living room, had pizza delivery guys participate in wrestling matches, asked locksmiths to help me break into a safe, and so on. A two-day shoot would yield seven or eight comedy bits.

That particular week I shot in Vegas on Thursday and Friday and planned to stay through Saturday night to attend the Oscar De La Hoya–Bernard Hopkins fight at the MGM. I bet a lot of money on Hopkins (a 2-to-1 favorite) and figured it’s always more fun to lose in person.

As I was finishing up the hidden camera bits on Friday, I get a call from Melissa. (She had mercifully ditched the Trojanowski name at this point.)

“Come home, I’m ovulating.”

An interesting surprise. Back at the turn of the century, you couldn’t find out if you were ovulating by asking Siri. You had to make your own fertility calendar out of beets.

It was a pain in the ass to get back to Los Angeles on such short notice, especially with my weekend plans, but you can’t just take months off from the pregnancy quest, so I jumped on a Southwest flight and met Melissa at an Outback Steakhouse by the Burbank airport. After sharing a Bloomin’ Onion and Kookaburra Wings, we made relations in our bed, then I jumped on a plane and flew back to Las Vegas to witness Bernard Hopkins KO De La Hoya with a kidney punch.

This frantic fertility quest worked out. Nine months later we had our first son. As far as names went, we could’ve gone with Oscar or Bernard to pay tribute to the fight. Or maybe throw Outback Steakhouse a bone. “Barbie” or “Ribeye” Iacono kind of had a ring to it. Instead, we got lazy, breezed through the A’s in the book, and settled on Archie, which happens to be the name of my favorite TV character of all time: Archie Bunker.

One month into Archie Iacono’s life, I was scheduled to appear on Jimmy Kimmel Live! for my birthday to present a hidden camera bit I had shot at a jewelry store.

When I got to the couch, Jimmy surprised me by introducing my childhood crush pop star Debbie Gibson. I was infatuated with Debbie Gibson as a sixteen-year-old. Try as I might, I just couldn’t shake… her love. Debbie’s poster hung in my room right next to Genesis, Rowdy Roddy Piper, and Huey Lewis and the News. That was my pubescent Mount Rushmore.

Debbie grew up a few towns over from me and was the same age. I remember going to the Jones Beach Theater with my friend Allison to see her in concert. We had the worst seats. Our backs were literally against the back wall. I brought a sign that said “Kiss Me, Debbie—It’s My Birthday.” So corny, but it actually didn’t matter, since being in the last row in the upper deck, Allison and I were the only ones who could see the sign.

And now here we were, twenty-eight years later to the day, and Debbie Gibson was singing “Lost in Your Eyes” while gazing into mine. It was a ridiculous scene. I thought it would be funny to just get up and leave, but I felt bad that she had come all the way out to do this, so I stayed and let the embarrassment rush over me.

A few miles away, Melissa was watching the East Coast ABC feed at home. She was super-hormonal, having just given birth to Archie, and was very upset about this faux birthday date. But as part of my birthday gift and because she’s a great lady, Melissa didn’t let me know until years later how upset she was. Debbie probably wasn’t thrilled with it, either.

When our second child was born, I bugged Melissa to come up with a silly name. We both liked Jack for a first name and I had the idea of Tripper for his middle name. What a way to honor John Ritter, the late great comedic actor. Ritter played Jack Tripper on Three’s Company. He had passed away a few years earlier and was widely known as one of the nicest guys to ever step foot in Hollywood, let alone the Regal Beagle.

“Jack Tripper Iacono” had a ring to it, but not a ring my wife was fond of. (At this point she was skeptical about the one on her finger, too.)

So we went with my backup plan: “Jack Romo Iacono.” Cowboys quarterback Tony Romo was my adult idol. It’s weird: I have a problem with anyone over thirty-five years old wearing a jersey with a current player’s name on it, but naming your kid after someone younger than you? Totally fine. Besides, Romo hadn’t won anything. I figured it’s easy to name your son after Joe Montana or Wayne Gretzky, but an athlete might be extra-inspired to achieve greatness if he or she hears people are saddling their spawn with their name. Melissa reluctantly agreed and we went with Jack Romo.

Melissa Reluctantly Agreed should’ve been the title of this book.

Melissa has witnessed me pull out my gambling tally sheet tens of thousands of times during meals, recitals, communions, bar mitzvahs, funerals, and any inappropriate time you can imagine.

She has endured me bringing a miniature TV to her best friend’s wedding. To my credit I kept it hidden underneath our table, illuminating the room so that all in attendance could only surmise that there was a spaceship landing by our feet.

She has handled my gift for flatulence with dignity and tolerance.

She has dealt with my insane family for more than twenty years. From cutting my father’s toenails to wiping my autistic sister’s rear end, caring for the Iaconos has not been a walk in the park by any means.

And she lets it all slide with a head shake and a smile that could brighten up a Malaysian cave.

Melissa Trojanowski is an absolute saint—and not the kind that cost me $28,750 by blowing the 2019 NFC championship game. The holy kind.

The only thing I did right by her was allow her to change that horrible last name. Aside from that, I don’t deserve her. It might be the case that no one does. She’s a –10,000,000,000,000 lock to advance to heaven. And that’s the easiest bet there is.