David Webb has been crowned Southend United’s greatest manager of all time, securing 44% of the vote in a fan poll. The former Shrimpers boss, who led the club to historic promotion in 1989/90 and a brief stint in the second tier, remains a beloved figure at Roots Hall. Next fixture: vs Eastleigh (at home, 2027-02-16) (13th in the table).
How did Webb achieve legendary status at Southend?
Webb’s legacy is built on two unforgettable seasons. In 1989/90, he guided Southend to promotion from Division Four, culminating in Ian Benjamin’s legendary goal at Bury. The following season, the Shrimpers defied expectations by reaching the second tier for the first time in their history, even topping the table briefly after a 4-0 win over Newcastle United on New Year’s Day.
Why do fans still adore Webb today?
Despite mixed memories of his departure, Webb’s impact endures. He recalls the “tempestuous” relationship with Vic Jobson but cherishes the unwavering support of the fans. “It was the best time of my managerial career,” he said. “The fans were always good to me.” His team, featuring stars like Chris Powell and Peter Butler, remains etched in Southend folklore.
What could have been for Southend under Webb?
Webb’s biggest regret is falling short of the top flight. “I always have that thought about not being able to do that last little bit,” he admitted. Yet, he remains hopeful his son Daniel, now in management, might achieve what he couldn’t. Webb’s era remains a golden chapter in Southend’s history, a reminder of what the club can achieve at its best.
