Johnny Crossan: £40,000 to Manchester City, January 1965
Sunderland's first big sale of the post-war era came at the beginning of 1965, when inside-left Johnny Crossan was enticed to the blue half of Manchester. 48 goals in just 99 appearances for the red and whites - including 22 in the promotion-winning season of 1963/64 - was enough to persuade City boss George Poyser to part with £40,000 for his services. There, Crossan managed another promotion, this time as captain, but he would never reach the heights of his Roker Park days, as a car crash effectively ended his ability to continue competing regularly at a high level.
Jim Baxter: £100,000 to Nottingham Forest, December 1967
By the time James Curran Baxter arrived on Wearside his best days had passed, yet he still managed to show up each of his teammates with alarming regularity. A relatively unsuccessful spell in the northeast culminated after two and a half years, when Nottingham Forest signed him for a six-figure sum. Forming an off-field partnership with the not very aptly named Gary Sobers - the pair were referred to as 'Drunk and Sobers' - Baxter's drinking grew as his star faded. An ill-fated return to Rangers followed before he retired to a life of alcoholism at the age of just 31.
Micky Horswill and Dennis Tueart: £225,000 (plus Tony Towers) to Manchester City, March 1974
Before he took to making an arse of himself on local radio, Micky Horswill was quite a good little footballer. So good, in fact, that the Annfield Plain midfielder found himself part of a deal whereby both he and FA Cup winning teammate Dennis Tueart wound up at Maine Road, with Tony Towers and a little under a quarter of a million pounds coming the other way. Horswill's time in Manchester was short-lived; he made just 14 appearances before moving on to unremarkable spells at Plymouth Argyle and Hull City. Tueart, however, found himself something of a hero in sky blue, scoring a memorable overhead-kick in the 1976 League Cup Final victory.
Barry Venison: £250,000 to Liverpool, July 1986
A shining light in a bleak period of Sunderland's history, Venison was always likely to move onto bigger and better things, and so it proved when he moved to Liverpool after exactly 200 starts for the Black Cats. There is little doubt here whether it was the right move for him: two league titles, an FA Cup and four Charity Shield wins speak for themselves. Venison then moved back to the northeast, aiding Newcastle in their 1993 promotion, before spells at Galatasaray and Southampton.
Marco Gabbiadini: £1,800,000 to Crystal Palace, October 1991
Perhaps one of the most galling things to come out of Sunderland's relegation in 1991 was the prompt departure of Marco Gabbiadini: fan favourite, goalscorer, Mag-slayer. Palace, fresh from the £2.5m sale of Ian Wright to Arsenal, had money to spend, and Sunderland couldn't afford to turn it down. Gabbiadini's spell in London was brief and miserable, before an enjoyable time at Derby County arrived. From there, he ventured far and wide but, much like Crossan, would never score as many goals anywhere else as he had on Wearside.
Michael Bridges: £5,000,000 to Leeds United, July 1999
It is telling of the cruel luck that befell Michael Bridges that his highest number of appearances for a single club came at Sunderland - with just 84 the figure. 76 of those came at the beginning of his career in his first spell on Wearside, where the showcasing of his raw talent encouraged the rampant money spending beast that was Leeds United to part with £5m for his services. Their decision initially looked a good one, as Bridges fired home a hat-trick on his debut, and 19 in all in his first season at Elland Road. Unfortunately, it was all downhill from there, and Bridges is currently plying his trade in the Australian A-League for Newcastle Jets.
Don Hutchison: £5,000,000 to West Ham United, August 2001
A revelation in a single season at Sunderland, Hutchison's time on Wearside was insanely short-lived. Seeking pastures new and money greater, he moved south to West Ham, for a then club record fee, and promptly saw the bottom fall out of his career. Ligament troubles did much of the damage, and after four years at The Hammers he resigned himself to an ignominious end to his career in the lower leagues.
Dean Whitehead: £5,000,000 to Stoke City, July 2009
Dean Whitehead's sale represents a rare moment of outstanding business for Sunderland in recent years. The midfielder was signed for an eventual fee of £150,000, and sold five years later for more than thirty times the price. Tony Pulis' decision to splash £5m on Whitehead was something of a shock, but he continued to be a reliable presence in the potteries, making over 150 appearances for another side in red and white. He is currently looking for a new club, having been released earlier this month.
Lorik Cana: £5,000,000 to Galatasaray, July 2010
Another one-season wonder, Cana divided opinion on Wearside with his enigmatic (see: crazy) style of play. Something of a liability, he left a year after signing for an identical fee, bound for the fanatics of Galatasaray. Here too, he found fan favour, but also the inside of the treatment room. He moved on to Lazio, where he still remains, but his appearances over the past three years have been infrequent.
Kenwyne Jones: £8,000,000 to Stoke City, August 2010
Jones was unplayable on his day; unwatchable off it. His time at Sunderland was fairly successful, nabbing 26 goals at a ratio just shy of one-in-three. His partnership with Darren Bent was a fruitful one but, when Stoke City offered a club record £8m, the time was right to sell. There he remains, but surely as an unhappy figure. Last season saw him notch just three goals, and ended in controversy as he fell out with teammate Glenn Whelan over an ill-judged dressing room prank which resulted in Jones smashing the latter's car windscreen.
Darren Bent: £18,000,000 (rising to £24,000,000) to Aston Villa, January 2011
Surely no man has gone from universal admiration on Wearside to universal hatred in so short a time. Darren Bent had scored at a rate better than one every other game in his year and a half at Sunderland, before suddenly handing in a transfer request the day after a lackadaisical showing against Newcastle. Within forty-eight hours he was at Villa Park, smiling from ear to ear, his accountants doing the same. Unsurprisingly, he hit the ground running, but the man with England ambitions has long since fallen into a state of disrepair. Usurped by Christian Benteke in Paul Lambert's thoughts, Bent is rumoured to be considering buying the plot surrounding the Villa bench to use as his own living quarters.
Jordan Henderson: £16,000,000 (rising to £20,000,000) to Liverpool, June 2011
The greatest product yet to come out of the Academy of Light, Jordan Henderson was proof of the merits of a good youth setup. Unfairly maligned by some, Henderson was a crucial member of the first-team between 2009 and 2011 - his match winning performance against Wigan Athletic in April of the latter almost single-handedly saved Steve Bruce's men from relegation. The outlandish fee Liverpool paid for him heaped pressure upon his shoulders but, under the guidance of Brendan Rodgers, Henderson is slowly starting to show his undoubted class. It would be of little surprise to see him evolve into an England regular in the coming years.
Asamoah Gyan: £6,000,000 (after a £6,000,000 loan fee) to Al-Ain, July 2012
Returning for the 2011/12 season looking overweight and disinterested, Asamoah Gyan's rapid departure from Wearside saw him quickly lined up alongside Darren Bent in the 'people we don't like anymore' queue. Gyan's first season at Sunderland had been a success, with the World Cup star notching ten goals and showcasing some fairly outrageous dance moves. But, blinking into the middle-east and seeing dollar signs staring back at him, the Ghanaian gave it all up for a payday in the sun (in a way, at least there was some mitigation for this move, even if it was only the weather) and an expensive loan turned into a relatively inexpensive permanent move. Two consecutive league titles have since followed, along with Gyan being the top scorer in the much-lauded UAE Pro-League.