I think Brunhilde's was the most painful, for me at any rate. Especially as it was box 13 that had the biggie, and 13 is her lucky number. At filming it seemed she picked the box without realising it was 13, perhaps she just picked the person behind it?? And she was like, Oh m God, what did i do? I didn't want to pick 13! As she needed the money for her daughter, it was even worse. She was really upset afterwards. She deserved so much more

Michael's game has to be up there with the worst, although I felt worse for his wife than him.

I think Tink (deal final offer of £2,900 for an OPL with £15k in her box) could possibly be a contender... and also Sarah from Thursday, simply because her deal came at a time when the banker was in charge anyway... and it didn't contribute to the players' luck.

A few more that haven't been mentioned:

Terri, who just seemed to fall apart and make bizarre decisions as the game went on, saying what she should do then doing the exact opposite, turning down generous offers, taking a crap one and ending up with an OPL.

I've never seen it but Alan's from January '06 sounds pretty awful...completely destroying the board, cutting his losses with a £1k deal then having £5k in his box (which was twice as much as his highest offer!)

Debbie from DDW taking out every red except the £250k, dealing for £15k then having it in her box, for the biggest ever Banker victory.

Bianca underselling a £3k box and being in floods of tears.

Orry's swap, if the extra £1k makes it count as a "red win"...

Of the ones in the poll I think the worst for me were Christine, Stevie and Dot...Dot's was probably the worst overall though, as she seemed so upset at what was happening and was really gutted that she hadn't dealt earlier. Plus she timed it completely dreadfully - taking the 2nd or 6th offers would have made a great game but she pushed her luck too far and then didn't push it any further and ended up with almost the worst possible result. If the £35k had been in her box I think I'd have actually had to kill myself...

(Oh and it's not quite what you were asking for but I found Bunney's red win pretty damn painful...)

Going with that theory, I'm saying Chantelle's 35k win, I was actually willing her to win 1p for being so annoying and so disrespectful towards the really good offers she was getting (and most of the forum now wants to shoot me).....

And another one nobody's mentioned but I found it prettty horrible was Rita from June, dealing for £7,500 after taking out nearly every safety net after the £250,000 and thinking she was going to have it in her box, and halving the lowest deal for the 250k box record. It didn't even feel that good when she didn't have it!

I don't think she was disrespectful towards them at all. She just didn't want to take them!

Anyways, Christine got my vote of the ones you listed, as the mere thought of selling a £100,000 for £6,000 is horrendous, but overall it'd probably be Orry for me. Another I'm very surprised that hasn't been mentioned yet is Kelsie!

If you are classing Orry's win as a red win, then his definitely.

Another one that just struck me: why hasn't anyone mentioned Rachel on Xmas day 06 yet, becuase that was quite horrible - and she had the power 5 in her box, unlike Michael (but at least the deal was a bigger percentage of the one remaining big value, at least she picked the 2 good prizes at the end, and at least she hadn't turned down over 9 times more like Michael) - maybe just everyone's forgotten it thanks to Wrighty's feel-good game a few hours later!

Can't believe I forgot that one!! That's probably second after Dot's for me to be honest.

I thought his wife crying really got on my wick a bit. And Michael was one suprise. I thought ah hes no dealing then he said DEAL

Let's give this a revival

Any contenders from the later years?

I didn't see it but wasn't there in the last year or two (the Box 23 era) where someone no-dealt around £30,000 at 11-box and ended up dealing something like £2,000 and turning down Box 23 which would have got them extra?

That would be Claire from November 2015. She crashed to £2,300 (3 box button offer on 2 blues/£15k) and £15,000 went in the next box plus Box 23 had NOTHING so at least she narrowly avoided a total crash.

She didn't take it that badly from what I saw.

A more painful one from my perspective was £4,450 Matt from May 2014, as he dealt £8,900 at 5 box, missed out of 100k, then lost half his deal to Box 23, and he really felt stupid and beat himself up for taking the wrong gamble there in the end.

Yes that was the one I meant now I've looked it up, I think I got mixed up with another game for the Box 23 - it probably was Jen? who sold the £250k for about £10,000 then turned down 23 and it had DOUBLE in it but no idea how she took it as never saw that game.

Whatabout Esher who swapped away 75k for a 1k I remember the Banker's comments after that game "Self Belief can win you a lot of money but it can also rob you of a lot of money"

I often joke that her game was so painful that it scared Kestral away from the forum, as that was his last commentary and posts until recently.

Think after all this time it's pretty hard to topple Barbara from 2006. One of the few occasions where to this day I believe the contestant is still having major regrets. The 100k was *there*, about to be opened. And it was swapped for absolutely no reason at all, Mally/Mark baseless logic.

Oh yeah, she was forever nicknamed “Swappy Barbara” on here afterwards!

The swap seems to be a thing of the past, don’t think it’s been offered in live play or proveout at all in the new series. I remember them even occasionally offering it at the start instead of the first monetary offer!

I still remember word-for-word her speech after giving it away and taught it to my son as it made him laugh so much I wonder if Barbara realises her legacy 17 years later

It was her decision, alright? There were---th---th---reasons---it's just that her fingers were---there were, it was her decision, OK? Her decision.