Landon Emenalo’s second professional contract, which commits him to Chelsea until 2031, will be celebrated as joyfully in Baltimore as it is in Cobham.
That is where his older brother Seb, 19, is playing as a freshman guard for Loyola Maryland Greyhounds, a Division I college in the NCAA basketball system. The two eldest sons of Michael Emenalo, former Chelsea technical director and Nigeria international footballer, are on twin sporting tracks that could, in the best-case scenario, lead them to become the first siblings ever to play in the Premier League and the NBA at the same time.
An ocean and several time zones separate the two brothers, but according to sources familiar with Landon, 18, and Seb — who, like all of those spoken to by The Athletic for this article, asked to remain anonymous to protect relationships — they remain as close now as they were growing up in the Emenalo household in leafy Surrey. Back then, there was a natural dynamic to their play: Landon with the instinctive talent for striking the ball with his feet, Seb with the unusually large wingspan and aptitude for catching it in his hands.
It was Seb who joined Chelsea’s academy first as a goalkeeper, the position his mother Erin had played for the University of Portland and then for the Washington Freedom in the United States’ first women’s professional sports league. Landon, who entered Cobham as an under-8, took after his father as a versatile player who could operate in the back line or in midfield.
Sport was not compulsory for either boy; education was always the priority, with football and American sports regarded by their parents as a healthy antidote to boredom as well as an alternative to less productive distractions. Emenalo Sr’s career ensured that football was always part of their environment, and on their visits to Cobham, they gained early exposure to the commitment and mentality of elite athletes.
The drive to take sport seriously came from within. Landon fell in love with football quickly and voiced his readiness to play for Chelsea to his family before he had even tried out for an academy spot. Seb’s relationship with the sport was different, and during his time at the ACS International School in Cobham, it was basketball that began to command his interest.
Interest morphed into obsession in the summer of 2017, when Seb watched LeBron James lead the Cleveland Cavaliers back to the NBA Finals and found his sporting idol. A few months later, the Emenalo family moved to Monaco when Michael resigned as Chelsea technical director and became sporting director at the Ligue 1 club. Landon accompanied him, joining Monaco’s academy, but Seb instead took every opportunity to strike out on his own and play basketball.
When they returned to England two years later, Seb quickly got involved in competitive local basketball, representing Surrey Rams and Thames Valley Cavaliers. Landon and Chelsea’s academy had mutual interest in a reunion, but he could not immediately register at Cobham. In an attempt to stay sharp and maintain his fitness while he waited, he played for a local amateur team — and ended up on the receiving end of a tackle that ruptured his anterior cruciate ligament.
If the surgery and lengthy rehab process that followed were not mentally challenging enough, Landon then suffered from Osgood-Schlatter’s pain in both knees as he went through a growth spurt. Chelsea stuck with him throughout, and the signing of his scholarship contract in July 2024 provided emotional confirmation that his physical problems were behind him.
By then, Seb’s love affair with basketball had taken him to the other side of the world, to the NBA Global Academy in Canberra, Australia. There he spent two years honing his skills and growing, both in maturity and quite literally: he now stands 6ft 6in tall with a rangy, flexible frame that is well-suited to a modern basketball guard. He also did well enough athletically and academically to earn a scholarship to Loyola Maryland, committing to the Greyhounds last summer.
Landon is significantly shorter than his older brother (he is listed as 5ft 11in), but carries himself with a poise and presence beyond his years.
He was fast-tracked into first-team training by Mauricio Pochettino shortly after his 16th birthday in January 2024, and made the substitutes bench on several occasions under Enzo Maresca, most notably Chelsea’s 2-1 win over Liverpool at Stamford Bridge in October. It was no surprise to see him involved in Liam Rosenior’s first training session as head coach in January.
“Landon is a very good footballer,” John Terry said during a live-streamed fundraiser for his foundation on Whatnot last year. “I think he plays for the first team and comes through. He currently plays left-back, he’s not a left-back, he can play left centre-half, he prefers to play in midfield as a six. A big future, a really good player.
Terry’s public praise caught Landon by surprise. Kind words mean more from a club legend, and particularly one who still pays such close attention to the academy talent coming through Cobham. It chimes with his own belief that he is ready for first-team football, but he is prepared to be patient in order to earn that opportunity at Chelsea. Along the way, he will have a firm decision to make about his international future; he has represented England and United States at youth level, and is also eligible for Nigeria.
Seb, who has played basketball for Great Britain at under-18 level, is similarly grounded. As a freshman role player at Loyola University Maryland, the 2026 NBA draft is not a realistic option. He knows his development is likely to be a more gradual process of earning the trust of his coaching staff and team-mates, with the aim of developing his on-ball scoring and playmaking.
There are few sporting environments in the world more competitive for a young athlete than Chelsea’s academy or NCAA Division I basketball. Just by making it to this stage of their respective journeys, Landon and Seb have already distinguished themselves as exceptional young talents, but their ambitions are far from satisfied. If they achieve them, the Emenalo family’s proud sporting pedigree will scale historic new heights.
