Late on Tuesday night, Steve McClaren quit as manager of the Jamaica national team minutes after his side failed to take the last automatic World Cup qualifying spot from CONCACAF. Jamaica were beaten to the spot by tiny Curacao, who became the smallest nation to ever qualify when they held Jamaica to a 0-0 draw in Kingston.
"It is the responsibility of the leader to step forward, take accountability and make decisions in the best interests of the team," he said in typically frank fashion as he announced that he'd be stepping even though Jamaica can still make it to the World Cup via the inter-continental playoffs in March 2026.
"Sometimes the best thing a leader can do is to recognise when a fresh voice, new energy and a different perspective is required to move this team forward."
ESPN takes a look at the highs and lows of McClaren's intriguing career on the sidelines.
The highs
The Treble in 1999
He wasn't the manager, but as assistant to Sir Alex Ferguson, McClaren played a key role in Manchester United's epic treble in '99. He had joined halfway through the season, replacing the well-liked Brian Kidd, and was acclaimed for his role in shaping the tactics that powered United to the league, FA Cup and UEFA Champions League titles in his first season. "For me, it was certainly the toughest but the most memorable five months in my career," he would say later.
In each of his three seasons as Ferguson's assistant, he would win the Premier League title.
Unprecedent success at Middlesborough
In his first season as head coach, McClaren guided Middlesborough to the FA Cup semifinal, beating former employers Manchester United en-route, before guiding them to League Cup glory in 2003-04. It was the club's first-ever title and guaranteed them European football for the first time in their 128-year history, while McClaren became the first English manager to win a major tournament in England since Brian Little in 1996.
The following season he finished seventh in the league, the club's highest finish in the first division since 1975, before following that up with guiding the club to the UEFA Cup final in 2005-06. It was the first time an Englishman had coached a club to a major European final since Sir Bobby Robson in 1997.
He had plenty of detractors at the time for his 'dour' style of play, but he remains the most decorated manager in Boro history.
Winning the Eredivisie with Twente
McClaren joined Twente at the lowest point of his career after being sacked by England (more on that later) but was an instant hit in the Dutch league. He guided them to second in his first season, got them to the KNVB Cup final, and got them out of the group stages of the UEFA Cup for the first time in 30 years.
The next season he went one better and led them to their first ever Eredivisie title, climbing to the top of the league in October and staying there despite immense pressure from giants Ajax. For the win, he was awarded the Rinus Michel Award for Dutch manager of the season as he became the first Englishman to win a top-division title as manager since Sir Bobby Robson with Porto in 1995-96.
McClaren would say, "Winning the Carling Cup with Middlesbrough was special, but this is pretty much right up at the top of anything I've ever done. To win a championship in a foreign country with foreign coaches, I think it's made me stronger."
The lows
Jamaica lose out to Curacao
We start with the latest, and Jamaica's inexplicable loss in what is already one of the great stories of the 2026 World Cup. McClaren had made a solid start to his time with Jamaica, as they won their first two games without conceding. A loss away to Curacao and a draw to Trinidad and Tobago, either side of beating Bermuda, though, meant they needed to win their last match against Curacao on Tuesday.
They had 60% possession on the night, 13 shots and 4 'big chances' but simply couldn't break down the underdogs' defence.
England miss out on the Euros
McClaren made several bold moves as England manager, including dropping senior statesmen David Beckham, Sol Campbell and David James as he looked to take England in "a different direction." He started qualification for UEFA Euro 2008 with two wins before stumbling, with England scoring just once in the next five matches and that eventually led to a situation where they needed to avoid a loss to already qualified Croatia to qualify for the summer tournament.
They lost 3-2 at Wembley, in a match where his selection decisions were heavily criticised, and that meant England missed out on a major tournament for the first time since the 1994 World Cup and missed out on the European Championships for the first time since 1984.
The news of his sacking the next day was predictable as 'wally with a brolly' headlines were written. His tenure remains the second shortest for a full-time England manager: he managed 18 games (9W, 4D, 5L) across 16 months.
Early dismissals at Wolfsburg, Nottingham Forest and Newcastle United
After his success with Twente, McClaren joined Wolfsburg to become the first Englishman to take charge of a Bundesliga club. He started poorly, losing the first three league games and a series of poor results meant he was sacked in early February 2011. Later that year, he joined Nottingham Forest but resigned after winning only eight points in his first ten games in charge in the Championship.
In 2015, he signed a three-year deal with Newcastle United. Here again, he started poorly. It took him nine games to register his first win with the club, but things didn't take a turn for the better from there. He managed them in 31 games with a poor 7W, 6D, 18L record - the 22.58% win percentage is the lowest he's ever had as manager (It was 29.17% at Wolfsburg and 23.08% at Forest).