Oostenders: Zech Medley’s unconventional path to York
From the bench with Bukayo to Bromley via Belgium
York’s transfer business went up a gear last Friday with the announcement of four new signings. One of the new recruits is 25-year-old defender Zech Medley: what qualities will he bring to the club, and what might we learn from his interesting career trajectory so far?
The first thing that jumps out about Zech Medley is his size: at 6ft 5, he strikes an imposing figure. Given his height, it’s no surprise that having started out as a winger in the Chelsea academy, Medley’s favoured position evolved first to left-back and eventually centre-back, where he has played most of his football since. He was highly rated as a youth prospect, making 8 appearances for England U16s alongside other talents from his age group including the likes of Marc Guehi, Phil Foden and Harrison Male, who was in goal for the Young Lions for Medley’s debut against Japan.
At the age of 16, Medley made the move across London to Arsenal where he signed his first professional contract. In 2017/18, he broke his way into the Arsenal U23 side and helped them win the PL2, then the following season caught the eye of then-manager Unai Emery enough to be included in the first-team squad. Medley made his debut in a Europa League tie against Vorskla Poltava, coming off the bench to play in front of Petr Cech in goal as the Gunners saw out a 3-0 win - another notable debutant for Arsenal that night was Bukayo Saka.
With first-team opportunities limited, though, Medley was sent out on loan to League One Gillingham in 2020/21 to gain greater experience of senior football. After 18 appearances for the Gills, he was recalled by Arsenal then sent on another loan to Kilmarnock for the remainder of the season. He scored his first goal in professional football at Killie, but couldn’t prevent their relegation from the Scottish Premiership that season.
Medley departed Arsenal in summer 2021 in search of regular first-team football, moving to Belgian Pro League outfit KV Oostende. He did play a decent amount of football there, making 66 appearances across three seasons and even occasionally being used as an emergency forward, but it was a difficult time for the club due to the off-the-pitch troubles. With the owners struggling to keep on top of mounting debts, Oostende were relegated from the top flight in 2023, then a year later the club was declared bankrupt and dissolved, leaving Medley seeking new employers.
At this point, Medley returned to the English game, joining League Two Fleetwood Town on a two-year deal, but his time there got off to a nightmare start as he suffered a ruptured Achilles in his fourth appearance. The injury kept him out of action for almost the entire season, only returning for a handful of games in April. The 2025/26 season saw him get more regular playing time for the Fishermen, occasionally playing at left wing-back rather than his more typical centre-back role.
Following the exit of Fleetwood manager Pete Wild in January, Medley made a surprise loan move to League Two pace-setters Bromley, reuniting with boss Andy Woodman who he had worked with in the Arsenal youth setup. His debut at centre-back earned positive reviews, and while he was in and out of the team after that, he played a part in helping the Ravens secure the League Two title ahead of higher profile clubs. With his contract at Fleetwood expiring this summer, some expected Medley to make a permanent move to Bromley: the hosts of the From Bromley With Love podcast expressed a desire to see him return, citing his versatility and ability as reasons why he could step up to League One with them, while expressing some doubts about his consistency.
It’s the Minstermen who have secured Medley’s signing, though, so where might we expect him to fit in? It seems likely that he will primarily compete with Mark Kitching for the left-sided centre-back spot. As a physically imposing defender who is also comfortable bringing the ball out of defence, he fits the profile City have looked for in these positions previously, and as a left footer he would add balance to the back three if played there.
While Medley has played at left-back and left wing-back on occasion, Stuart Maynard tends to prefer more attacking options at left wing-back, prioritising attacking threat and crossing ability. Medley’s heat map from a recent game for Bromley against Cambridge shows most of his touches coming in his own half, which is more similar to Kitching for York last season than players such as Ben Brookes or Alex Newby who were used at wing-back. It may in fact be more likely that Kitching could move out to left wing-back if Medley starts on the left of the back three.
Medley will be hoping for better luck with his move to York, after Oostende’s financial troubles marred his spell in Belgium and injury derailed his time at Fleetwood. His potential is clear, and at 25 he should be ready to enter the prime of his career. He may need to adapt to a new playing style, with City’s possession-heavy system differing from the more functional or direct approaches taken by Pete Wild’s Fleetwood and Andy Woodman’s Bromley. But, as a player honed in an Arsenal youth system that placed great emphasis on technical skill, this style may bring out the best in him.