Barnsley's decision to axe Andy Ritchie came under further scrutiny after resurgent Southend cruised into the FA Cup fourth round at Oakwell.
In what must be a first for English football, Ritchie was sacked last November for not spending enough money on new players.
Tykes chairman Gordon Shepherd handed Academy manager Simon Davey the managerial reins, but his decision is looking increasingly ill-fated.
Goals either side of the break from Kevin Maher and Lee Bradbury handed Southend a comfortable victory amid a chorus of boos from the home supporters.
While Southend extended their unbeaten run to six games, encouraging hopes they can beat the drop, Barnsley appear to be sinking fast.
They have won only one of their last 10 games and this uninspiring display prompted choruses of 'One Andy Ritchie, there's only one Andy Ritchie' from the Oakwell crowd.
Ultimately, however, the Barnsley supporters were drowned out by Southend's delirious small band of fans, who can now look forward to a fourth-round trip to Cardiff or Tottenham.
The Shrimpers subjected Manchester United to an embarrassing Carling Cup exit earlier this season before losing in extra-time to Martin Jol's men at White Hart Lane.
Staving off the threat of relegation remains Southend's priority, but they would certainly relish another trip to Spurs.
The early exchanges of this victory were awful and characterised by a series of misplaced and undercooked passes by both sides, but Southend always looked more dangerous in attack.
Freddy Eastwood, whose stunning free-kick earned the famous 1-0 victory against Sir Alex Ferguson's side, flickered into life in the 15th minute.
The Shrimpers frontman, whose goalscoring exploits this seasons have attracted admiring glances from a clutch of higher-placed clubs, outstripped the home defence down the right flank.
A wicked ball across the face of goal was crying out to be driven into the net but Martin Devaney tracked back to avert the danger.
Southend forged ahead, however, in the 22nd minute when skipper Maher was afforded the time and space to curl a delightful 20-yard strike into the top left-hand corner.
It was Southend's first shot on target but Barnsley threatened an immediate riposte when Daniel Nardiello connected with Paul Hayes' left-wing cross but headed straight at Darryl Flahavan.
And the Shrimpers almost extended their lead five minutes before the break when Eastwood narrowly failed to make proper contact with a header inside the six-yard box.
Four minutes later, however, Michael Coulson should have drawn Barnsley level when he broke clear but hit a low shot straight into Flahavan's midriff.
Moments later Hayes found himself unmarked at the far post as Barnsley's fightback gathered momentum.
There remained the lingering suspicion that Southend could clinch a killer second on the counter-attack and that threat materialised shortly before the hour mark.
Alan McCormack jinked his way to the byline and crossed for Bradbury, who took a touch six yards from goal before swivelling to rifle home a left-foot shot.
It should have been worse for Barnsley as Eastwood and Jamal Campbell-Ryce blew further opportunities to pile the misery on the crestfallen hosts.
Teams:
Barnsley Colgan, Hassell, Atkinson, Paul Reid, Heckingbottom,Hayes, Togwell, Howard, Devaney, Nardiello (Richards 65),Coulson.
Subs Not Used: Lucas, Kay, Tonge, Williams.
Booked: Howard.
Southend Flahavan, Hammell, Hunt, Barrett, Clarke,Campbell-Ryce (Guttridge 81), Gower, Maher, McCormack,Eastwood, Bradbury (Harrold 81).
Subs Not Used: Sodje, Hooper, Welch.
Goals: Maher 22, Bradbury 58.
Att: 4,944
Ref: C Oliver (Northumberland).