Simon Dawkins
A late-blooming footballer who traded England for Jamaica's national team, then seamlessly pivoted to coaching in the American lower leagues.
Born 1987 (age 39)·Jamaican footballer·Birthday: December 1·Millennials
Biography
Simon Dawkins' career is a story of patience and reinvention. A technically gifted midfielder in Tottenham Hotspur's academy, his path to the first team was blocked, leading to a series of loan spells that never quite ignited. His breakthrough arrived unexpectedly in California, with a loan to the San Jose Earthquakes in MLS. There, his clever passing and driving runs made him a fan favorite and proved he could thrive as a professional. This form earned him a call-up to the Jamaican national team, for whom he qualified through his father, and he became a crucial part of their squad that reached two consecutive CONCACAF Gold Cup finals. After stints back in England and the US, injuries began to take their toll. Rather than fade away, Dawkins immediately stepped into coaching, first as a youth coach at his former club San Jose and then, in a bold move, as the interim head coach for USL Championship side Monterey Bay FC in 2024, demonstrating a sharp football mind ready for its next chapter.
Millennials
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.
Simon was born in 1987, 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.
#1 When Simon Was Born
The biggest hits of 1987
#1 Movie
Three Men and a Baby
Best Picture
The Last Emperor
#1 TV Show
The Cosby Show
Simon's Life & Times
The world at every milestone
1987Born
Black Monday stock market crash
Gas: $0.90/galHome: $72,400Min wage: $3.35/hrPresident: Ronald Reagan"Walk Like an Egyptian" — The BanglesBest Picture: The Last Emperor
1992Started school
LA riots after Rodney King verdict
Gas: $1.13/galHome: $84,300Min wage: $4.25/hrPresident: George H.W. Bush"End of the Road" — Boyz II MenBest Picture: Unforgiven
2000Became a teenager
Y2K passes without incident; contested Bush-Gore election
Gas: $1.51/galHome: $119,600Min wage: $5.15/hrPresident: Bill Clinton"Breathe" — Faith HillBest Picture: Gladiator
2003Could drive
US invades Iraq; Human Genome Project completed
Gas: $1.59/galHome: $146,000Min wage: $5.15/hrPresident: George W. Bush"In Da Club" — 50 CentBest Picture: The Lord of the Rings: The Return of the King
2005Could vote
Hurricane Katrina devastates New Orleans; YouTube launches
Gas: $2.30/galHome: $167,500Min wage: $5.15/hrPresident: George W. Bush"We Belong Together" — Mariah CareyBest Picture: Crash
2008Turned 21
Barack Obama elected first Black US president; financial crisis
Gas: $3.27/galHome: $153,100Min wage: $6.55/hrPresident: George W. Bush"Low" — Flo RidaBest Picture: Slumdog Millionaire
2017Turned 30
#MeToo movement; solar eclipse crosses the US
Gas: $2.42/galHome: $195,000Min wage: $7.25/hrPresident: Donald Trump"Shape of You" — Ed SheeranBest Picture: The Shape of Water
2026Age 39 today
Gas: $3.91/galPresident: Donald Trump
Key Achievements
- Earned over 20 caps for the Jamaica national team, helping them reach the CONCACAF Gold Cup final in 2015 and 2017.
- Won the MLS Supporters' Shield in 2012 as a key player for the San Jose Earthquakes.
- Scored a memorable solo goal in the 2015 CONCACAF Gold Cup semifinal to help Jamaica defeat the United States.
- Served as interim head coach for USL Championship club Monterey Bay FC during the 2024 season.
Did You Know?
He was teammates with global star Gareth Bale during their time together at Tottenham Hotspur's academy.
He played for Derby County in the English Football League Championship after his time in MLS.
His middle name, Jonathan, is shared with his father.
He holds both British and Jamaican citizenship.
“Sometimes you have to go a different route to find where you fit.”
