Simon Woolley speeds past with a smile and a handshake to take a call before we start. I arrived early and am waiting on a chair outside Woolley’s office, feeling like I am back in secondary school. The Principal’s Office is in the Neo-Gothic extension to the original Homerton College buildings from 1876. The serene garden, trees and hedges in front of the building separate us from the busy main road into the centre of Cambridge.
As we make our way into his office, he explains that a student is organising an event, but that there’s been a misunderstanding with one of the speakers about fees. Woolley is negotiating on the student’s behalf. For him it’s an example of the activist approach he’s bringing to the 257-year-old institution and the message he is giving students. “I want you to feel that you’ve got a sense of purpose, not just for yourself, but for society,” he said.
Around Woolley’s office are a selection of black artworks and framed photographs from his 30-year career as an activist, first with the democracy campaign Charter 88 and then as a founder of Operation Black Vote (OBV). OBV and Woolley as its leader are credited with transforming the British parliamentary landscape from an overwhelmingly white institution and persuading political parties across the spectrum to actively seek the support of black and minority-ethnic voters.
Woolley brings my attention to a photo of the civil rights leader Jesse Jackson, who came to Homerton to receive an honorary fellowship and who was Woolley’s mentor for years. “I would watch him go into an auditorium of 5,000 people, and he would walk on stage,” he says. “The first thing he would do on stage is tell the crowd, ‘this didn’t just happen. A lot of people put it together.’ And he would say, ‘can I get the organisers to please stand up?’ And you bring them on stage. And then he would say, ‘can I get the auxiliary staff on stage to take a bow?’”
Woolley’s education and life are hardly those you might expect of the principal of a Cambridge college. Born Christmas Eve 1961, Woolley was taken to an orphanage at age two by his mother, Lolita, a nurse originally from Barbados, who had been separated from her husband when she had a brief relationship with Woolley’s father. Young Simon was adopted and raised by a white working-class couple, Phillis and Dan Fox, in Leicester, together with Mick, an older black boy they had adopted before and who became Simon’s brother. “My mother was an incredibly warm woman, incredibly giving,” he says. His adoptive father worked long hours and passed away suddenly when Simon was 14. “I never spoke to my dad, I just knew his love.”
Working-class life in Leicester meant that you had to hustle to survive, Woolley explains. His mother cared for other local kids, providing what we might now describe as an informal breakfast club and after-school club. She was often paid in-kind, and by one parent in homemade clothes of extremely variable quality that Simon and Mick would have to wear. When he was older, 11 or 12, Woolley would tout tickets to local football games. “I’d give my mum some money, and then we would go out and buy some clothes. The money that we got gave us immense self-worth and pride that we were the architects of our success.”
The hustle is a life skill and one that Woolley is proud to have taught his son. “When he went to his senior school, he was buying and selling sweets,” he recalls, adding that a teacher complained, incorrectly, that this was “extortion”. That experience didn’t put Woolley’s son off from moving into trading trainers, NFTs and now, as a 20-year-old economics student, crypto. “I was worried in the last ten years that I’d be edging to middle class,” he said, “and when you’re middle class, I think it’s a challenge to impart the hustler spirit to your children, because most hustles come from an absolute need.”
Woolley loves clothes and, when we meet, is wearing a smart suit jacket over a dark turtleneck. “Black people would not have the luxury that Dominic Cummings had to walk into the gates of Downing Street looking like a tramp,” he says. “If a black person looked like him, they would be arrested, tasered.”
“I think being working-class too, the other thing that we were acutely aware of – and I think a lot of people are, in no small measure – that having money and looking good meant that you could be less disrespected, not quite sure more respected, but definitely less disrespected,” he adds.
It was also growing up in Leicester in the 1970s that brought Woolley to understand and experience racism. “You knew you were black, you knew you wanted something, but you knew that people didn’t like you because of the way you looked, and you had to invent your own pride, black pride, on your terms,” he says.
During this period, Leicester had an influx of East African Asians, mostly from Uganda where they had been expelled by the British-backed dictator Idi Amin. The arrival of the new community had a profound impact on race relations in the city. “White groups would say, ‘you’re like us’ and we wanted to accept that, shamefully,” he said. In one incident from the time, Woolley witnessed an elderly Sikh man being savagely beaten by white skinheads.
After leaving school, he went to work as an apprentice in a garage and then into an advertising sales in London. By his mid-twenties, he had made enough to buy two flats.
“I say to my son, who’s now 20, ‘having money, is not about being flashy. It’s about the luxury for horrible people not to have agency over you. And if you’re black or brown, if people have agency over you, it’s the most undignifying, humiliating reality,’” he says. He recalls one incident early on in London when he was told to leave a flat by a racist landlord and another when he went to ask for a £100 overdraft and a bank manager looked him up and down and refused.
Not one to stray far from the hustle, Woolley was also drawn to the ticket touting scene in West London, seeing and admiring the touts working their way through the theatre set. “I loved their vernacular, the language. I loved their sharpness,” he says. “The tragedy for most of them was that they found it difficult to find a pathway out on the street to so-called respectability.”
Woolley still felt something was missing from his life. “[I] felt less than, because I didn’t have a degree if I didn’t have an A-Level,” he remembers. Eventually at 27 he quit his sales job, drove his Volkswagen Polo up to Epping College and asked to begin studying for A-Levels. “They looked at me, and they could see that I wasn’t 17,” he says. They put him on an access course, for older students, instead. From there he went to the University of Middlesex.
After university Woolley joined Charter 88, the constitutional and democratic campaign organisation launched in a special edition of the New Statesman with the involvement of then editor Stuart Weir. Charter 88 called for a written constitution, open government, electoral reform and devolution.
In 1996, he set up up Operation Black Vote (OBV). OBV builds the political power of black and minority ethnic communities and directs that towards securing better representation. It was in this role that Woolley unleashed his hustler talents on an incredibly white political establishment. “I’d call the Prime Minister’s office and say, ‘look, the shadow prime minister’s coming to an event, and so Lib Dems and the Conservatives are coming, they both said, ‘yes’, we’re going to leave an empty chair for you if you don’t come.” It proved an effective strategy at opening doors for a small organisation largely run on good will.
OBV’s strategy was always to work across the political spectrum, rather than associating to the Labour Party, historically the party that most ethnic minority voters supported. Woolley and fellow activists calculated and highlighted the constituencies where the majority of the sitting MP was less than the number of black and minority ethnic people and ran electoral registration campaigns.
“We convinced the Conservatives, through every single leader since John Major, that they could have some political skin in the game if there’s greater representation,” Woolley explains. OBV ran mentoring programs that placed aspiring politicians with elected representatives, giving them a valuable step up. Notable alumni of the mentoring schemes include Helen Grant, Clive Lewis, Marsha de Cordova, Tan Dhesi, Baroness Sayeeda Warsi and Marvin Rees.
30 years on from the founding of OBV there are 90 “BAME” members of parliament representing Labour, the Conservatives, Lib Dems, and Independents. It’s a big success, but one that reveals of the shortcomings of representation.
“Whilst we changed the colour, we didn’t change the nature of British politics, which in some ways has worked against us,” Woolley says. “Now, particularly the Conservatives, but also today, in the Labour front bench, you’ve got black and brown people doing awful things to other black and brown people.”
“The idea that you can’t belong to this country for 20 years, goes against everything that we should stand for,” he says, referencing one of the policies announced by Home Secretary Shabana Mahmood to restrict immigration and asylum rights, justified in part as a response to rising racism.
“It’s a bit shameful that I spent most of my adult life fighting for black and brown people to be in the highest places in the land, only for them to use their racial identity as cover to implement policies that undermine being black or brown in this country,” he says. Woolley adds that Mahmood, Priti Patel and Kemi Badenoch have all implemented “racist policies” while claiming they could not be racist, but admits he thought this “would be the preserve of the Conservatives”.
Ironically, it was a Conservative Prime Minister, Theresa May, who appointed Woolley to the House of Lords as a crossbencher in her resignation honours. At OBV, Woolley cultivated links across the political spectrum and this eventually led him to serve as an unpaid advisor to the Race Disparity Unit (RDU) set up under the May government. The purpose of the RDU was to audit and publish information on race equality across government services, and then to challenge those departments to “explain or change” why racial disparity was present in those services or policy areas. However, when Boris Johnson became prime minister, he replaced many of the people working with the RDU, including Woolley.
For the moment, Woolley is focused on changing Homerton College. “On my door, you won’t see ‘Lord Simon Woolley’ you’ll see Simon,” he says. In his first few days in the role, he insisted on spending time understanding how the cleaning, maintenance and gardening staff worked. “I remember being in the canteen. This is in the Great Hall, it’s like a Harry Potter Hall, and they [students] would come in and they would be nudging each other, ‘we’re being served by a Lord!’” he said.
In a call back to the example set by Jesse Jackson, Woolley will call out by name and thank each member of staff at the end of every formal dinner, because they value the praise and because of the example it sets to the 300-odd people in the room. “I want the students to, above all, leave Homerton College with a great sense of what decency looks like and how it’s not just given as charity. It’s about how you are, how you interact with people on a daily basis,” he said.
Woolley has three years left in his term of office. He is the first black man to lead a Cambridge college. “I’m probably one of the most scrutinised heads of houses in Oxford or Cambridge with bear traps everywhere. It comes with the territory,” he said. I ask him if he feels a pressure to succeed. “I reverse that,” he says. “So it’s the pressure not to fail, and that’s tough. And then when I get out of that malaise, I revert to ‘just be you’, the rest will sort itself out.”
[Further reading: Keir Starmer, the tragic matador]
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