Danny Cowley’s assistant is currently second in the bookies’ running to take over the reins at Plough Lane.
Among the top contenders is ex-Charlton boss Johnnie Jackson, Ipswich under-23s coach John McGreal and former Huddersfield boss Chris Powell.
It comes after Mark Bowen stepped down from his role following the Dons’ final day relegation to League Two.
After being appointed in February, his side failed to win a league match under his tenure - seeing the South London side finish the League One campaign 23rd on 37 points.
The 46-year-old’s appointment would make it an emotional return to Plough Lane for Bassey, who came through the youth set-up as a player with Wimbledon FC.
He then rejoined the Dons in 2002 to see out his final playing days, before announcing his retirement in 2004 due to injury.
After he hung up his boots, the former midfielder would spend the next 15 years as part of the Wombles’ backroom staff - playing a key role in returning the club back to the Football League before departing in 2019.
His return to Plough Lane would also see him link up with former Fratton favourite Lee Brown after he left PO4 during the January window.
Former Wimbledon striker Lyle Tyler recently admitted Bassey had a major part in the Dons’ success, claiming he had a role to play in every signing made by the club.
After a brief stint at Barnet, the 46-year-old joined Cowley’s new backroom set-up last summer as the former Lincoln head coach began an overhaul of his playing squad and coaching staff.
Should the odds speak truth, it would mean Pompey would have to go in search of another replacement of a key figure in Cowley's backroom staff.
The Blues are currently in the process of searching for a new head of football operations, after Roberto Gagliardi departed the role in February.
The Fratton Park outfit targeted Forest Green’s head of recruitment Richard Hughes as their first choice but had the deal scuppered after 11th-hour talks with the Gloucestershire side.
As Pompey continue their search for a new head of football, Bassey’s departure could signal even bigger problems for Cowley this summer.