Hibernian is actively searching for left-wingback options this summer, a surprising move given that this position has been a strength in the squad. With Nicky Cadden and Jordan Obita both out of contract next summer and having dealt with injuries during the 2025/26 campaign, the club is in need of a succession plan. Cadden will celebrate his 30th birthday in September, while Obita turns 33 in December, making it essential for Hibernian to find capable replacements. The club is looking for players who can operate effectively as both left-backs in a four-man defense and left-wingbacks in the favored 3-5-2 formation under manager David Gray. In the latest edition of the Hibs Observer's Scouting Scotland series, five potential candidates have been highlighted. Two of these prospects hail from England's Premier League 2, while another two have shown promise in the Scottish Championship. The fifth player is a former SPFL defender currently making waves in Northern Ireland. One notable name is Henry Fieldson, a 20-year-old free agent from Queen's Park, who has attracted attention after a successful season in the Championship. His versatility and strong performances make him an appealing option for Hibernian as they look to bolster their left-wingback position.