The Crewe contest saw Labour's 'Tory Toff' campaign backfire into a drubbing of historic proportions. It went so badly that Number 10 disowned the strategy even though the PM's political secretary Fiona Gordon spent at least ten days in Crewe helping to direct the campaign.
Next up was Henley where, while Labour was never going to win, third place was taken for granted. The spending limit for by-elections is £100,000 and with Labour Party finances in crisis, the decision was made to go through the by-election motions while spending as little as possible. This strategy saw Labour come fifth, behind the Greens and the BNP.
David Davis' resignation proved a quandary for the Labour leadership, not least because of its surprise value. Polls insisted that more than 60 per cent of the public support 42-day detention, presumably mostly in Tory areas, yet Davis is a popular local MP.
There was some discussion that maybe Labour should have contested the seat on a civil liberties and security agenda, but to have taken on Davis would have required the full £100,000 spend and would have legitimised his quixotic endeavour.
The most serious contest of all now faces Brown. Glasgow East MP David Marshall is resigning on the grounds of ill health. In 2005, Labour polled 60 per cent of the vote and the SNP attracted the support of 17 per cent.
In normal times it would be inconceivable that Labour could lose the seat, but Alec Salmond is riding high in the polls, Wendy Alexander has resigned her position leaving Labour leaderless in Scotland, and the seat itself has a notoriously low turnout, making it susceptible to a large swing.
In Glasgow East, Brown has no choice but to find the necessary £100,000 and to throw the kitchen sink at this by-election. Labour faces the very real prospect of losing one of the safest seats in Britain and doing so would make his continuing leadership untenable.
Alex Hilton is a Labour parliamentary candidate and founder of political blogs Labour home and Recess Monkey.