The letters sent by Rudy Cline-Thomas to the NBA ran into double figures, all but one of them posted without reply. A student at Providence College in Rhode Island, his senior year was about to start and he hoped to fill the summer before it with an internship. Basketball floated his boat.

Reebok had drawn his attention too and a stint of work experience with the sportswear giant was easier logistically. It would be based in Stoughton, within reach of Cline-Thomas’ home in Washington, and after quick correspondence, Reebok invited him in. But the NBA and the lights of New York were what he wanted and at the very last minute, after weeks of silence, the association offered its final placement to him. Cline-Thomas was given 24 hours to accept and jumped on the chance.

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In that instant the door opened to sport and business — two professions Cline-Thomas was equally and highly curious about. His persistence and the break it earned him could, by way of several other enterprises, take him into the boardroom at Leeds United shortly.

The Athletic has learned that as part of the pending takeover of Leeds by 49ers Enterprises, a deal which should complete in the next few weeks, Cline-Thomas is among the candidates for a position on the club’s board of directors, an executive role for a key figure in the investment group funding the acquisition. His appointment, if it materialises as anticipated, will become official once 49ers Enterprises has approval from the English Football League (EFL) for its 100 per cent buy-out.

Cline-Thomas is well known in business circles in the US, a spirited and savvy entrepreneur who worked as a basketball agent soon after graduating from Providence in finance and accounting, and whose business ideas led to him co-founding Mastry Ventures in 2021, a venture-capital firm based in New York. He is a member of the pool of main investors brought together by 49ers Enterprises in preparation for its takeover at Elland Road.

In England his name is less familiar, though Cline-Thomas is believed to have family ties to the city of Leeds. His parents originated from Sierra Leone before emigrating and settling long-term in the USA and Washington, where Cline-Thomas was born.

In America, his father worked in business and through him, Cline-Thomas caught the bug. He had been sent to study at Providence as a Martin Luther King scholar, a scheme created to support prospective students from ethnic-minority backgrounds, and with finance qualifications behind him, his NBA internship in New York in the early 2000s set everything rolling. He would later tell an audience of students at Providence that a tentative step into basketball “changed his life”.

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Cline-Thomas loved the sport but was not good enough to chase a career in it. He knew a player who had been drafted into the NBA, Steve Francis, and Francis — then minus an agent — asked Cline-Thomas if he had any advice about how to manage himself. It made Cline-Thomas think that operating as a basketball agent would be a productive avenue to pursue.

After college he secured himself a job with Williams & Connolly, a Washington-based law firm which had a specific department assigned to representing professional and emerging athletes. The model at Williams & Connolly was different from most player agencies. Whereas the typical agency charged sportspeople a contingency fee — effectively a cut of contractual or commercial deals they helped to negotiate — Williams & Connolly charged by the hour, making itself and its guidance more accessible. When Cline-Thomas joined, Grant Hill and Tim Duncan were two of the basketball stars on their books. Cline-Thomas became one of the youngest agents in the NBA.

What helped to shape his future path was his success in vying to represent Andre Iguodala. Iguodala, a four-time NBA winner, was young and on the roster of the Philadelphia 76ers. Competition to sign him to an agency was intense. Cline-Thomas sold himself to Iguodala and when Iguodala moved to Golden State Warriors later in his career, the transfer took him and Cline-Thomas into Silicon Valley, the land where entrepreneurial energy is always white hot.

More and more, Cline-Thomas began to mix in venture-capitalists’ circles and understand the investment potential presented by companies which were newly formed or developing there. He also noticed a prevalent lack of ethnic diversity at the top of those businesses — something he is likely to see in many of the boards that run English football clubs.

Cline-Thomas’ answer was to establish Blueprint, a wealth-management company for basketball players and athletes in general. His intention wasn’t just to look after sportspeople or do everything for them. His aim was to open their eyes to the business world and to give the athletes he worked with, many of them black, opportunities they might not otherwise get.

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Iguodala, a clever and switched-on character, had access to the Warriors’ locker room and team-mates were intrigued about what he was doing. He and Cline-Thomas began investing in different start-up companies, injecting sums from $25,000 (£19,500) up into six-figure sums. A large number of the firms they went for were consumer or tech-based. Zoom was one of those targeted. Other players observed and considered using their money in the same way. In 2017, Cline-Thomas was pictured on the front of Bloomberg Businessweek with Iguodala and Steph Curry, the Warriors’ pin-up.

All three were responsible for launching the Players Technology Summit six years ago, a corporate gathering attended by entrepreneurs and venture-capitalists which looked at guiding athletes, particularly those from the African-American community, into the realms of big business. Cline-Thomas was established in it himself, engaging with Gucci and contributing to the production of a basketball documentary, The Scheme, with HBO.

In 2021 he co-founded Mastry, an investment vehicle in 49ers’ territory, San Francisco, which focused on early-stage initiatives and entrepreneurial ideas in its infancy. Uber was one of the companies it put money into, and it is thought that Cline-Thomas’ investment in Leeds is being made via Mastry.

Mastry made headlines in a bigger way in February of this year when it acquired a majority stake in Athletes First, a firm which represents American Football players in the NFL. Cline-Thomas, at a stroke, became chairman of Athletes First, moving to the top of the NFL’s biggest agency.

In the US, his connections to the sporting world are obvious. But in England, and away from Leeds, he has already been involved in another football investment, not unlike the process through which 49ers Enterprises initially bought its way into United in 2018. Last August, a US fund by the name of Argyle Green negotiated the purchase of a 20 per cent stake of Plymouth Argyle for £4million. Cline-Thomas was named among the investors backing the purchase.

Argyle won promotion from League One in the season that followed, claiming the title, and they will share a division with Leeds next term. To comply with EFL regulations and to avoid any conflict of interest as part of 49ers Enterprises’ takeover, Cline-Thomas is expected to cut his ties by disposing of his small stake in Plymouth and gifting it back to the Devon club. It clears the way for Leeds to install him as a director.

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Even with Leeds relegated and outside the Premier League for at least the next 12 months, the executive role at Elland Road will provide a new level of exposure for a man who is not known for courting personal publicity. 49ers Enterprises aims to drive Leeds back into the Premier League quickly, a competition with a profile like very few others around the globe, and with the prospect of securing a board position below that of chairman-to-be Paraag Marathe, Cline-Thomas is in new territory again.

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He might pinch himself when he walks into the club’s stadium for the first time, remembering the genesis of his career: letter after letter, banging on the NBA’s door, refusing to be stonewalled or take no for an answer.

(Top photo: David Paul Morris/Bloomberg via Getty Images)