[5][b] Other signings included goalkeeper Charles Cotton from West Ham, outside right Arthur Holden from Portsmouth, and centre-forward Harold Halse from Wanstead, plus players from Southend Athletic, Grays United, South Weald and Leigh Ramblers.
While the fraud squad investigated, Robert Maxwell and Ken Bates stepped in, at Jobson's request, to lend the necessary money to the club to repay its Christmas savers.
On New Year's Day, 1992, the club briefly topped the Second Division but their dreary late season form stopped any hopes of a unique third successive promotion that would have given them a place as a Premier League founder member.
David Webb left Yeovil Town and was appointed the new manager, signing players Darryl Flahavan, Leon Cort, Tes Bramble and Mark Rawle.
This was the last professional appearance of Shaun Goater; fans from his former club Manchester City came to give him a special send-off at the end of a long and distinguished career.
Southend had injuries to strikers Billy Paynter and Lee Bradbury while Matt Harrold was cup tied so boss Steve Tilson partnered Gary Hooper up front with Freddy Eastwood.
On their return to League One Southend had bolstered their squad, adding Striker Charlie MacDonald, Winger Tommy Black and centre midfielder Nicky Bailey to their ranks.
Despite the sale of Freddy Eastwood, Southend finished sixth in League One at the end of 2007–08 much to the thanks Lee Barnard, a January signing from Tottenham Hotspur, scoring 9 goals in 13 games, thus qualifying for a play-off place against Doncaster Rovers.
Manager Steve Tilson was delighted to bring Freedman to Roots Hall adding some much needed experience to Southend's forward line, something The Blues had been without since the retirement of Shaun Goater.
Tilson also signed goalkeeper Steve Mildenhall from Yeovil Town as his new number one following the departure of Darryl Flahavan and the shot stopper became a firm favourite with the Southend fans.
A dismal run of just one win in 2010 left Southend deep in trouble at the wrong end of the table, relegation was confirmed on 24 April 2010 away to Oldham despite twice coming from behind to earn a 2–2 draw.
The Guardian reported "A previous high court hearing was told that HMRC originally presented a winding-up petition for a tax bill of £690,000, but applied to have the club put into administration when the debt became larger.
[28] Southend chairman Ron Martin claimed that he was refusing to pay because the initial tax bill of £2.1 million was overpaid, the winding up petition was adjourned for 28 days.
The club mounted a more serious challenge the following season, spending 11 weeks at the top of League 2, owing to the goals and form of Ryan Hall, Kane Ferdinand and Liam Dickinson.
[48] On 2 March, Martin confirmed Southend was under an EFL transfer embargo due to an unpaid tax bill,[49] while February's wages to players were not paid on time, resulting in further PFA involvement.
[56] On 2 April 2020, during the COVID-19 pandemic in the United Kingdom, Southend put "several staff and some players" on furlough (temporary leave) under the UK Government's emergency job retention scheme.
Phil Brown returned as manager[66][67] but could not rescue the situation; Southend suffered a second successive relegation on 1 May 2021 with a game to spare despite a 2–1 victory at Barrow, dropping out of the Football League after 101 years.
After members of staff were late receiving their October 2022 salaries,[91] the Shrimpers Trust and shirt sponsor PG Site Services each loaned the club £40,000,[92] a gesture described by CEO Tom Lawrence as "humbling".
[99] In a 25 January 2023 statement, Martin could not "outline precise timings" regarding the bridging finance;[100] he was later reported to be seeking a £5M loan to pay debts including £1.4M in unpaid tax owed to HMRC.
[105] On 10 February 2023, St John Ambulance stopped providing first aid staff at Southend home games because of outstanding fees,[106] forcing the club to find alternative medical cover ahead of an FA Trophy tie with York City.
[123] Three companies, including PG Site Services and Engie Power, were also involved in the petition regarding a £275,000 debt,[124] but the hearing was adjourned to 12 July 2023, giving Martin more time to sell the club.
[135] While players were eventually paid, manager Maher and other backroom staff remained unpaid three days before the winding-up hearing, while club sale discussions were reportedly being held up by the stadium side of the transaction.
[155] With a matchday squad of just 15 players due to the club's transfer embargo, Southend won their opening two games of the season, beating Oldham Athletic[156] and Dagenham & Redbridge,[157] but lost the next two.
The Shrimpers Trust Board expressed interest to the fund in bringing "ownership of the freehold of Roots Hall Stadium and its facilities into the hands of those who value it most – our local community of Southend-on-Sea".
[177] The club signed former West Ham goalkeeper David Martin to make his immediate debut, with Portuguese midfielder Mauro Vilhete one of just two substitutes,[178] as Southend won 2–0.
[195] The club would remain at Roots Hall, with the 500 homes once planned for the site now transferred to Fossetts Farm[196] (a move agreed by Southend's council in early November).
[202][203] However, on 8 March 2024, Southend CEO Tom Lawrence said final completion of the club's takeover could still be a couple of months away, being dependent upon a council review of the housing shift to Fossets Farm,[204] though it later emerged that obtaining the consent of Ron and son Jack Martin's finance partner (CBRE) was also delaying matters.
[211] By 8 May 2024, it was clear the sale would not be completed by mid-May; the council's due diligence over plans for the housing at Fossetts Farm continued, while CBRE had yet to consent to the payment structure for the Roots Hall refurbishment.
[222] While Citizen Housing had not met the council's 21 June deadline, there was sufficient progress to persuade Cowan to continue negotiations about new heads of terms ready for new due diligence.
The bond would remain in place until the COSU takeover was successfully concluded or the club could demonstrate it had sufficient resources to meet its financial obligations for the forthcoming season.