West Ham United were yesterday deciding whether to make a fourth offer for the Birmingham City defender Matthew Upson and whether to make an astonishing £14m attempt to prise the striker Darren Bent away Charlton Athletic before the transfer window closes on Wednesday night.
Upson, 27, is desperate to leave Birmingham and is believed to have made a personal plea to the club's co-owner, David Sullivan, after the Championship club rejected West Ham's third offer last week.
West Ham have bid £4m, £6m and £7.5m for Upson - with Birmingham understood to be holding out for £9m. The defender has 18 months left on his contract at St Andrew's but is adamant he wants to leave. Upson's frustrations have been fuelled by the belief that Birmingham have reneged on a verbal agreement he had with them that he could go, after four years at the club, if an offer of £6m was received.
Yesterday his agent, Barry Neville, said: "Matt is disappointed after having been told he could leave Birmingham for a certain amount - and what has been offered has gone way past that. As to whether he would be interested in a move to West Ham, that can't be answered until a bid has been accepted."
Arsenal, Upson's former club, are believed to be due 25 per cent of any sell-on fee.
West Ham's defensive crisis - Anton Ferdinand, Danny Gabbidon, James Collins and Lucas Neill are injured - has ensured the relegation-threatened club's continued interest in Upson. Executives, and the manager Alan Curbishley, spent yesterday looking at other targets, including the Dutch defender Ruud Knol, who plays for Vitesse Arnhem.
West Ham are expected to inquire about Bent but are not believed to be confident that their former manager, Alan Pardew, will sell to them at any price. Pardew has ruled out parting with his captain, who is injured, and West Ham are understood to have blocked a move to The Valley for Teddy Sheringham.
West Ham had planned to bid £12m for Bent. Some sources at Charlton believe they may sell if a club were to table £17m, although no clubs are expected to go that high for the England international.