Although Chris Wilder believes there is a possibility that Henderson will be allowed to spend a third season at Bramall Lane - two years after Manchester United initially dispatched him to South Yorkshire - the United manager acknowledges it could prove difficult to retain the youngster’s services given his career trajectory.
Having enhanced his reputation as one of the most promising talents in the Premier League last term, Henderson is set for showdown talks with Wilder’s counterpart Ole Gunnar Solskjaer about his future in the North-West. Aged 23, Henderson’s representatives are expected to demand their client is either installed as Old Trafford’s undisputed number one - a position David de Gea has held for nearly a decade - or made available for transfer, with Chelsea among a small army of clubs known to be monitoring the situation closely.
United hope the progress Henderson has made under the tutelage of Wilder and coach Darren Ward, combined with the relationship they have built up with the former England under-21 international, could offer both Solskjaer and the player a third way out of a situation complicated by de Gea’s estimated £350,000 a week salary. Returning to the club where he has kept 35 clean sheets in the past 24 months would guarantee Henderson the first choice status he craves and grant Solskjaer time - given his reluctance to sell - to ease the Spaniard off the payroll.
After setting his sights on representing his country at next summer’s European championships, Henderson knows anything other than regular first team football would effectively end his hopes of persuading Gareth Southgate to select him ahead of Jordan Pickford and Nick Pope.
Speaking before United finished ninth in the table only a season after gaining promotion to the top-flight, Wilder admitted he hoped Henderson’s future will be resolved quickly given the 2020/21 campaign is scheduled to start on September 12.
With Wes Foderingham arriving on a free transfer after leaving Rangers and Jake Eastwood joining Kilmarnock on loan, United - who have been linked with Trabzonspor’s Ugurcan Cakir and Aaron Ramsdale of AFC Bournemouth in recent weeks - are already taking steps to reorganise a department Wilder views as crucial to their hopes of establishing themselves at the highest level. However, with both Cakir and Ramsdale, who started his career with United before being sold for around £1m, both valued at more than 15 times that amount, it seems unlikely that Wilder would be able to strike a deal for either and continue his pursuit of Nottingham Forest defender Matt Cash unless the restrictions placed upon United’s recruitment budget following the Covid-19 pandemic are relaxed. United also have a confirmed interest in Reading midfielder John Swift, given the continued uncertainty over John Lundstram’s position at the club after failing to agree a new contract.