

A converted defensive lineman who forged a Pro Bowl career at guard through sheer athleticism and a relentless, blue-collar work ethic.
Kyle Long’s football narrative is one of dramatic reinvention. The son of Hall of Famer Howie Long, he initially followed a more chaotic path, playing baseball and bouncing between colleges as a defensive end. It was only at the University of Oregon that he made the switch to offensive line, a move that unlocked his prodigious potential. His raw power, surprising agility, and fierce competitive streak made him a first-round pick for the Chicago Bears in 2013. Long didn’t just live up to the pedigree; he carved his own identity, earning three consecutive Pro Bowl selections from 2013 to 2015. His playing style was a spectacle of controlled violence, often seen driving defenders far beyond the line of scrimmage. While injuries ultimately shortened his career, Long’s peak demonstrated a rare blend of elite genetics and self-made grit, establishing him not merely as a famous son, but as a dominant force in his own right.
1981–1996
The first digital natives. Grew up with the internet, came of age during 9/11 and the 2008 crash. Highly educated, deeply indebted, slower to marry and buy houses. Redefined work, identity, and what it means to be an adult.
Kyle was born in 1988, placing them squarely in the Millennials. The events that shaped this generation — the internet revolution, 9/11, and the 2008 financial crisis — shaped the world they entered and the choices available to them.
The biggest hits of 1988
#1 Movie
Rain Man
Best Picture
Rain Man
#1 TV Show
The Cosby Show
The world at every milestone
Pan Am Flight 103 bombed over Lockerbie
European Union officially established
September 11 attacks transform the world
Indian Ocean tsunami kills over 230,000
Twitter launches; Pluto reclassified as dwarf planet
Michael Jackson dies; Bitcoin created
Royal wedding of Harry and Meghan; Parkland shooting
He played only five games at offensive tackle for Oregon before being drafted in the first round as a guard.
Long was also a talented baseball pitcher in high school and was drafted by the Chicago White Sox in the 23rd round in 2008.
He and his brothers, Chris and Howie Jr., are the only trio of brothers to all be selected in the first round of the NFL draft.
He publicly announced his retirement from the NFL via a heartfelt letter on Twitter in 2020.
“I gave the game everything I had, and it gave me more than I could have ever imagined.”