There’s no guarantee that every bit of business conducted in the transfer market will prove a success.
Indeed, for every Colby Bishop, Lassana Diarra, Ricardo Rocha and Gavin Bazunu, there could easily be a Djimi Traore, Theofanis Gekas or Mike Williamson lying unexpectedly in await, too.
There’s no scientific explanation why a transfer can turn sour for one and be a huge success for another.
However, the nature of modern football, with players and managers changing clubs so often, means there's always going to be those who struggle to perform in a short space of time.
Like the majority of clubs, Pompey have found that out for themselves in recent years.
And with another transfer window on the horizon, the pressure will once again be on the Blues to get it right.
But what lessons can be learned?
Well, if the list below is anything to go on, there’s plenty of case studies to refer back to.
Of course, not everyone included is a bad player. It just didn't work out for them at Fratton Park for whatever reason.
The list doesn’t include anybody presently at the club. But let us know if there's anyone you think escaped it who deserves to be on the list from the Michael Eisner era.
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From left: John Marquis, Tyler Walker, Charlie Daniels and George Byers Photo: National World
2. Sylvain Deslandes
The Wolves loanee arrived in January 2018 with the aim of taking the 2016-17 League Two champions to a new level and bolster their new League One status. Yet the defender made just two appearances as he struggled to show the Fratton faithful why he was signed. Left with just 135 minutes of Pompey football under his belt. Photo: Joe Pepler
3. Conor Ronan
The attacking midfielder joined Pompey on loan at the same time as Deslandes from Wolves. In fairness, the then-20-year-old made 17 appearances for Kenny Jackett's side. But he left at the end of the season without really doing much. In fact, no goals or assists were recorded during his short stint at Fratton Park. The Irishman currently plays for the Colorado Rapids in the MLS, Photo: Joe Pepler
4. Louis Dennis
Signed from non-league Bromley on a free transfer, there was little to lose in Pompey handing the forward a chance in the Football League. Yet the step-up proved too much and Dennis left a year later with just eight Blues appearances and one goal to his name. A 41-minute run-out as a sub against Oxford was his only League One appearance. Photo: Joe Pepler