Kenny Jackett has missed out on adding Joe Newell to his Pompey squad.
The left-sided winger completed a switch to Hibernian on Sunday, signing a two-year deal.
Yet it is understood Jackett had also shown strong interest, keen to bring the free agent to Fratton Park.
Newell played under Jackett during his 40-day spell as Rotherham boss in 2016.
Subsequently, the availability of the 26-year-old following his end-of-season New York Stadium departure alerted his former manager.
However, with Pompey unable to move quickly, Newell instead chose Hibernian ahead of other suitors also including Peterborough and Doncaster.
The former Peterborough trainee made 31 outings in the Championship last season as Paul Warne’s side suffered relegation.
He totalled 150 appearances and netted 15 times for the Millers since joining in August 2015, but the expiry of his contract signalled a summer exit.
Jackett had indictated he would like to reunite with the winger on the south coast, but wasn’t in a position to swiftly complete a deal, thereby missing out.
Pompey last week sealed their first signing of the summer in Shrewsbury right-back James Bolton, arriving on a free transfer.
Meanwhile, Brighton’s pursuit of Matt Clarke continues, with the Blues holding out for £5m from the Premier League club.
Jamal Lowe has also attracted interest, although Millwall and Wigan have each failed with £1.5m bids for last season’s top scorer.
Jackett has been told by owners Tornante he can spend any transfer fees received for his players.