Chapter Summaries

1.Red Bull Flugtag and The Flying Ditkas – As part of its marketing and branding strategy tied to extreme sports, Red Bull created the “Flugtag.” German for “flying day,” the Flugtag is a contest in which teams of up to five people construct home-made, human-powered flying machines. Perched on a long ramp, high above a body of water, they then attempt to launch these flying machines – whether truly flight-worthy or not – to see who can travel the farthest before crashing into the water below. This chapter tells the story of how several friends and I beat out hundreds of applicants to compete in the Red Bull Flugtag in Chicago. Over the course of four months, we come together as a team to represent the city of Chicago and one of its greatest folk heroes, “Iron” Mike Ditka. Along the way, we become minor celebrities around town, appearing on magazines, morning shows, and social media. Our saga culminates with a detailed and hilarious account of the first and only flight of Ditka Airship I before 75,000 assembled fans along the Lake Michigan beachfront. Following our attempt to slip the surly bonds of Earth and touch the face of Ditka, we have the chance to share our experience with Da Coach himself.

2.Marathon – For much of my early life, it’s safe to say I wasn’t exactly the paragon of physical fitness. I viewed running as something to be avoided at all costs, akin to a form of corporal punishment. Maybe I had spent too much time listening to my brother, who was anti-running for evolutionary reasons – his theory being that nature had made him big enough to stop and kill anything that might be chasing him. As I got older, I worked hard to develop a better nutritional and exercise regimen that included running. Completing a marathon was the ultimate test for me to prove to myself that I had turned over a new leaf. After all, the first guy who ran one died! This chapter recounts the history of the modern-day marathon, along with my own personal struggles with running. It details my preparation to run a marathon and builds up to a mile-by-mile account of the race itself. It then concludes with my reflections on the race and its unexpected aftermath.

3.The Playboy Mansion – When I set out to write this book, I was a single, thirty-something guy who had been navigating my way through a string of short-term, superficial relationships. Perhaps cliché, but why not take advantage of this situation by partying with Hugh Hefner at the Playboy Mansion? This chapter tells the story of how I got into a party at the Mansion and provides a behind-the-scenes view of this secret world, from the Playmates to the Grotto to Hef himself. Along the way, I meet a menagerie of characters, undertake a late night adventure across Los Angeles, and finally begin to come to grips with my emotional need for something more meaningful in my life.

4.St. Patrick’s Day, Dublin – With the first name Liam, it’s safe to say that St. Patrick’s Day is a big deal to me. At the age of 22, a St. Patrick’s Day adventure that might as well have been conceived by James Joyce spawned the Hurlin’ o’ the Green, an annual party I have hosted ever since. As part of The Best Year Ever, I decided to take the Hurlin’ on the road and celebrate St. Patrick’s Day in Dublin. This chapter provides a historical view of St. Patrick and his feast day, contrasted with a modern day pub crawl across Dublin – with all of its associated hijinks and ballyhoo.

5.The Pope and St. Peter’s Basilica – I was raised a devout Catholic, attending Catholic school and celebrating mass several times per week until I left for college. Since then, I had joined the legion of more relaxed Catholics, still believing but not necessarily actively practicing my faith. Within this chapter, I travel to Rome during Holy Week to celebrate Mass in St. Peter’s Basilica with Pope Benedict XVI. I tour the religious marvels of Vatican City and Rome, the eternal city. And a special encounter with the Pope leads me to reflect on my own relationship with the Almighty.

6.Red Sox-Yankees and the Green Monster – I lived in Boston for three years while attending Harvard Law School. That period was the pinnacle of my academic career, which I then parleyed into a successful professional career. But like many of my classmates, I now questioned whether it was all worth it. Within this chapter, I travel back to Boston for my 10th year law school reunion and take in a Red Sox-Yankees game from atop the famed Green Monster. Part inside baseball, part The Paper Chase, this chapter provides an account of my experiences at Harvard and the reflections of my classmates and me one decade later – all set against the backdrop of a thrilling installment in baseball’s greatest rivalry.

7.St. Andrews, The Old Course – I grew up in Flint, Michigan, a city that became infamous almost 30 years ago due to Michael Moore’s documentary Roger & Me, which depicted it as the poster child for urban decay at the hands of evil General Motors. More recently, it was again in the headlines for a water crisis spawned by bureaucratic negligence of historic proportions. But to those of us who grew up there, Flint was just a typical Midwestern city; and one that was famous for something else – its own PGA golf tournament. The Buick Open sparked an interest in golf that grew in me over the years. I blossomed into an enthusiastic amateur who has traveled the world to play the game. In this chapter, I travel to the Home of Golf to play a round on the Old Course at St. Andrews. A shot-by-shot account of a round on the Old Course provides an opportunity to describe the history of this famous course, as well as a glimpse into the inner monologue and full spectrum of emotions experienced by a golfer on its links. I fully validate Bobby Jones’ maxim that “Competitive golf is played mainly on a five-and-a-half-inch course… the space between your ears.”

8.Lord Stanley’s Cup – Just days following the bankruptcy of General Motors, another nail in the coffin of a moribund Michigan economy, the Detroit Red Wings took the ice with a chance to win their second-straight Stanley Cup.This chapter delves into Detroit sports culture and the resilient, blue collar mindset that has seen the region through tough times. I follow the Red Wings through the Stanley Cup finals as the team attempts to repeat as winners of the oldest trophy in sports and reverse the narrative of Detroit as a dying city. A cameo by Christopher Walken highlights some of the unexpected twists and turns that take place during this quest for the Cup.

9.The World Series of Poker – At the height of the no-limit, Texas hold-em poker craze, I travel to Las Vegas to compete in the World Series of Poker. This chapter provides an account of what it’s really like to play against the game’s best – separating the curated myth of what you see on television from the cold hard reality of high-stakes poker. Much like the St. Andrews chapter, the reader gets to follow every hand I play and my thought process along the way – including the imagined backstory on each of my tablemates that played a not insignificant role in my decision-making.

10.The Running of the Bulls, Pamplona – Because no adventure narrative is complete without an event that risks life and limb, I travel to Pamplona to run with the bulls during the Festival of San Fermin. This chapter describes the often misunderstood history and logistics surrounding the Running of the Bulls each July. I provide a detailed account of the “Encierro” – the bulls, the set-up, the different sections of the route, and ultimate risks involved. The chapter climaxes with my actual run with the bulls, followed by that evening’s bull fight in the arena. To highlight the potential for danger, the first fatality from the running since 1995 occurs during my days in Pamplona.

11.Michigan-Notre Dame – My father was a poor Irish kid from New York City. His life was changed forever when he received a scholarship to play football for the University of Michigan. Michigan football was woven into the fabric of my family growing up, a form of religion to me. Within this chapter, I partner with the Michigan Children’s Hospital to get on the field for a Michigan-Notre Dame football game and hold up the famous M Club banner under which the team runs when taking the field. Along the way, I reflect on the highs and lows of my Michigan football “faith” and the lasting linkage it provides to my late father and my own aspirations as a parent.

12.Spicy Chorizo, Abe Lincoln, and the Big Red Machine – I sometimes refer to this as the “un-chapter” because it almost didn’t happen. It started out with an attempt to run with the Famous Racing Sausages during a Milwaukee Brewers game. But ironically, this was the sole event at which I was unsuccessful during the year. Meet God’s representative on Earth = no problem. Run in a foam sausage costume during a baseball game = no way. Faced with this cruel rejection, I search about for a worthy replacement event and end up throwing out the first pitch at a Cincinnati Reds game. All while masquerading as Cesar Geronimo. I somehow make sense of it all.