Second-year Michael Jolaosho is a versatile player capable of performing in the centre of midfield or as a centre-back. He scored his first Southend United goal when appearing for the Under-23s against Swindon Town in October 2026.

A strong presence in the centre of the park, capable of holding off opponents to build attacks, he showed leadership qualities when asked to captain the Under-17s for periods of 2025/26. Dual-registered with Isthmian League North Division outfit Concord Rangers, whom he helped to lift the Under-18s County Cup in 2026