The Mutesa II Stadium at Wankulukuku thrummed with anticipation, the air electric, the stands a sea of red.
A teenage Phillip Obwin, then a Kibuli SS student in 1993, was about to become theirs – a Red Eagle of Express, little knowing he’d one day don Villa’s blue, igniting passions and defying norms.
His boots, barely worn, carried the dreams of a boy from Buganda Road Flats.
This was no ordinary arrival. It marked the start of a career that wove through Express, SC Villa, URA, Nalubaale, and the Uganda Cranes, leaving a legacy of triumphs, controversies, and quiet resilience.
Decades later in a Kampala studio, Obwin sat across from me, Villa badge on his chest, voice steady but heavy with nostalgia.
This was The Game of Life – and ‘Phillo’, ‘Capi’, ‘Bollie’ unraveled a story of sacrifice, duty, and the dignity of work.
A rivalry’s reluctant renegade
Kampala, 1996: the city teetered on the edge of a football ‘world war.’ Obwin, Express’ most dependable defender, had chosen to cross to SC Villa, his boyhood love.
From then on, the Red Eagles faithful, scarves aloft, branded him a traitor, their chants of ‘Judas!’ echoing through Wankulukuku, Nakivubo and the Masaka Recreational Ground stands.
The blue end, in contrast, sang his name, hailing their returning son. ‘Villa was home, where my heart lay,’ Obwin told me, clad in Villa’s blue, voice steady.
But the move was a saga of defiance and division. Express officials, citing local football rules, blocked the transfer after Obwin’s starring role in their 1995 league and cup double.
For six months, he trained with Villa, refusing to play for Express, his resolve as unyielding as his tackles.
‘It never crossed my mind to leave Express,’ he convinced, ‘until Hajji Omar Ahmed Mandela said, ‘You boy, I want you. Are you ready to come and play for us?’ I said yes.’
Negotiations faltered, Express clinging to their star man, Villa demanding their prize.
Pubs from Wankulukuku to the city centre buzzed with heated arguments. Some called Obwin a mercenary, others a dreamer chasing his roots.
As a Cranes mainstay, his absence risked national team harmony, forcing Fufa to intervene.
After tense talks, Express relented, accepting Villa’s Shs6m offer – a decent fee then, given the circumstances.
Obwin was free, but the city’s divide deepened, Villa Park’s blue flags clashing with Express’s red fury.
In the derby matches between the two sides, every Obwin tackle drew the Red Eagles roar of fury, but once in a while a fan’s cry – ‘You were ours, Bollie!’- cut through the noise, a reminder of the bridges burned.
‘I’d served Express well,’ he said, unapologetic. ‘I won titles. It was time to experience Villa.’
As a child in Buganda Road Flats, Obwin had sneaked into Nakivubo to worship Villa’s giants – Ronald Vvubya, Magid Musisi, Paul Hasule.
‘I supported Villa from primary school,’ he said, eyes alight. In S1 at Old Kampala, coach Stephen ‘Jesus’ Mulinde spotted his talent.
‘He said, ‘You’re coming to Villa,” Obwin recalled. ‘I was terrified – a barefoot kid, playing with those legends? I refused.’
Fate pivoted in S5 at Kibuli SS. Mulinde asked why he’d shunned Villa. ‘I was afraid,’ Obwin admitted. ‘He said, ‘Now I’m taking you to Express FC’. I said yes.’
In 1993, under David Otti, Obwin joined Express, arriving about the same time as Edward Kalungi and Joseph Mutyaba.
He joined stars like Isaac Nkaada and George Ssimwogerere, who embraced him.
Obwin recalls with pride facing and containing KCCA’s Sam Simba in his early days at Express. ‘I was a kid, but I remember we won that game 1-0.”
By 1995, he’d won the league in his first season with Express, a Uganda Cup, and then a League and Cup double, reaching the Caf Champions League semi-finals, only to fall to Orlando Pirates.
‘We lost 1-0 in South Africa, drew 1-1 at home,’ he recalled. ‘Nakivubo was packed and we were winning with just a few minutes left.
‘But Gavin Lane’s header slipped through Abu Kigenyi’s legs. We thought he had handled the ball, but the ball was in the net.’
In 1998 after two years away, Express lured him back from Villa thanks to the Red Eagles rather controversial and influential manager Kassim Buyondo.
‘They wanted me,’ Obwin said. ‘Buyondo laid out the offer, and I returned.’ The Red Eagles faithful forgave him, but in 2001, Villa called again, under Milutin ‘Micho’ Sredojevic.
‘Hajji Mandela came back,’ he laughed. ‘I didn’t negotiate much. I decided.’ These back-to-back switches – Express to Villa, back to Express, then Villa again – set Kampala’s football culture alight.
As Villa launched Micho’s four-in-a-row title winning reign, the love-hate relationship between the two clubs only intensified, always sparking wild cheers from the blue stands and jeers from Express’s red wall.
Roots and resilience
Obwin grew up in Buganda Road Flats, where the ground where Kisozi House sits was his playground.
With three brothers and a sister, football was life. ‘We played barefoot, for fun,’ said the Shimoni Demonstration School pupil at the time, conjuring dusty pitches and laughter.
His father, a civil servant, and mother, a housewife, kept the family grounded, but tragedy struck early.
Obwin’s mother passed away when he was young, followed by his father during his A-levels at Kibuli SS.
‘I was in Sudan with Express, my first trip abroad, when dad died,’ he said, voice softening. ‘It was my first flight. I came back to the burial.’
Orphaned, Obwin became a father figure to his sister. The family had to leave the flats after his father’s death.
Express chairman at the time, Hassan Bulwadda, had offered him a house in Muyenga, but his siblings scattered – his sister going back to Kayunga, their parents’ village home, his brothers to friends’ homes.
‘I had to bring her back,’ he said. ‘A fan, a married man I trusted, housed her. I paid her fees while playing.’
His sister, now married with a family, calls him ‘Dad,’ a testament to his sacrifice. ‘She knows what I did,’ he said, pride in his eyes.
This duty shaped his choices. In 1995, a Nairobi-based football agent arranged trials at Portsmouth in the UK for Obwin and Fred Tamale.
‘Express was playing the Hedex Cup, and officials didn’t want us to go,’ he recalled.
‘The agent said, ‘They won’t wait. You’re not a known player.’ So I disappeared.’
Obwin stayed a week in Nairobi, then flew to England – with Tamale arriving way later, only for both to miss Portsmouth’s pre-season.
‘We trained for three days,’ he said. ‘They said, ‘We’ll contact you’ – a polite way of saying they wouldn’t take us. It was a punishment for arriving late.’
A later offer from a Turkish club faltered over Express’s high transfer fee. ‘If they’d asked for less, maybe I’d have made the move,’ he mused.
A former teammate urged him to remain in the UK, but he returned for his sister. ‘I promised to be there for her, to pay her fees,’ he said. Duty trumped ambition.
Glory days and controversies
At Express, Obwin won a league in his first season (1993), Uganda Cup (1994), and the league and cup double (1995).
They even reached the Caf Champions League semi-finals, falling narrowly to eventual winners Orlando Pirates.
At Villa under Milutin ‘Micho’ Sredojevic, he won a Uganda Cup and four consecutive league titles from 2001 to 2004. ‘Micho brought systems,’ Obwin said. ‘He taught us formations, how to think faster.’
But his name is also tied to the infamous 22-1 demolition of Akol FC in 2003. Allegations of match-fixing have never gone away.
‘Akol was weak,’ Obwin said, guarded. ‘They barely fielded 11 players. We were flying.’ He himself scored in that rout.
Although the result was later nullified, it was still in Villa’s favour as some of only nine Akol players that turned up for the beating were unregistered.
Cranes highs and unfulfilled promise
A versatile defender, Obwin captained every club he played for – and the Cranes.
‘I was never a substitute unless injured or carded,’ he said. His finest moment came in 2002, scoring the winner against Ghana at Namboole in a 2004 Afcon qualifier.
‘Beating a team of stars like Stephen Appiah and Sammy Kuffour felt good.’
Yet Nations Cup qualification eluded him. ‘We had talent,’ he said, ‘but the organisation was awful.’
From sleeping on carpets before losing 6-0 to Tunisia to the chaotic 2003 ‘juju’ clash with Rwanda, Uganda repeatedly fell short. Cecafa titles in 1996 and 2000 offered some consolation.
The final chapters
At URA, Obwin won the Uganda Cup (2005) and two league titles (2006, 2007). In 2008, Nalubaale offered a life-changing sign-on fee.
‘That money bought six acres in Bombo, built my house, started rentals,’ he said. But the club collapsed soon after.
He returned to Express for the last dance in 2010, but unpaid wages and family responsibilities pushed him into retirement that same year.
Life after football
Obwin invested wisely but insists he must keep working. Today, he is a distribution assistant at Nation Media Group (NMG).
‘Some say it’s not a job for a Cranes captain,’ he shrugged. ‘But no job is less. The maid, the driver, the digger – they’re all important.’
His children are his drive. Two attend King’s College Budo and Nabisunsa, others are in primary school. ‘That’s why I continue working,’ he said.
The quiet gentleman
For all his achievements, Obwin wears humility like a second skin. At NMG, some colleagues were shocked to discover the driver among them was the former Cranes captain.
On the streets, fans call out his name. ‘It’s awkward,’ he admitted. ‘They know your name, but you don’t know theirs. You smile, pretend you do.’
His lesson to the next generation? ‘Tell your truth. Your story might inspire someone.’
Phillip Obwin’s story is not just about football, but resilience, duty, and the dignity of work. Catch Obwin’s full story on The Game Of Life with this writer on YouTube.
Fact file
Full name: Phillip Obwin
Nicknames: Phillo, Capi, Bollie
Age: 49
Express FC: 1993-1996; 1998-2000; 2010
– Titles: League (1993); Uganda Cup (1994); League and Cup double (1995)
– Caf Champions League semi-finalist (1995, lost to Orlando Pirates).
SC Villa: 1996-1998; 2001-2004
– Titles: Multiple league titles (four-in-a-row 2001-2004 under Milutin ‘Micho’ Sredojevic); Uganda Cup
URA FC: 2005-2008
– Titles: Uganda Cup (2005); League (2006, 2007).
Nalubaale FC: 2008-2009
– Notes: Life-changing sign-on fee funded Bombo investments; left after owner vanished, player strike
International Career: Uganda Cranes (1994-2004)
– Key Highlights: Scored winner in 1-0 victory over Ghana in 2002 (2004 Afcon qualifier, Namboole)
– Won Cecafa titles (1996, 2000)