How do Hibs get themselves in a position to challenge for even the minor European places next season? Well, with apologies for cracking the obvious gag, you certainly wouldn’t start from here …
On a serious note, there are good reasons for Hibs fans to feel both excited and just a little terrified by the coming close season. Even if the potential arrival of a new technical director might generate a bit of energy around East Mains.
Because, sure, appointing the right person in the right place – nobody gets to pick the perfect moment in football, so forget about the third element of that mythical trifecta – would represent a start. But any in-depth study of how Hibs have worked the market over the past five years, under five different managers, is guaranteed to create some concerns.
They need a repeat of their greatest hits. Like landing Kevin Nisbet, a future Scotland international who would also turn a tidy profit when sold on. And they’ll need two or three deals of that calibre even to make a top-six finish any sort of certainty. Which means the people making the decisions need to be clear in their goals, clever in their dealings – and completely certain about every decision they make.
Regardless of how many voices participate in the initial filtering process, Hibs cannot afford to make more than one or two mistakes in an extremely busy transfer window. So let’s take a look at their track record, examining some of the hits, misses, slow burners and surprise packages to pitch up at Easter Road since the summer of 2019.
Loan deals are excluded unless they led to ‘permanent’ moves. And we’ve decided to ignore some of the ‘development signings’ made more as punts on potential, than genuine attempts to strengthen the first team. Which leaves us with a selection including:

5. Adam Jackson – Miss
Any debate on this one? A Paul Heckingbottom signing who had worked with the Hibs boss at Barnsley, Jackson played fairly regularly in the Covid-shortened 2019-20 campaign. But never really convinced as a dominant centre-half and was quietly allowed to join Lincoln City after a single season. | SNS Group

6. Marijan Cabraja - Hit(ish)
Cabraja returned to his native Croatia a just a year into his three-year deal, for personal reasons as much as anything football related. He played 26 times for Hibs last season – but eventually lost his place as starting left back to a resurgent Lewis Stevenson. Would have been nice to see him stay longer and compete for game time. Photo: Mark Scates - SNS Group

7. Demetri Mitchell – Miss
It’s never easy for a former Hearts player to become an Easter Road favourite. The fact that Mitchell had once jokingly asked “Hibs, who are they …” in response to a question about the great Edinburgh rivalry didn’t help. But neither did his performances in green-and-white. Arrived January 2022, left January 2023. Without anyone really missing him. | SNS Group

8. Christian Doidge – Hit
Never everyone’s cup of tea, stylistically. But the big man never gave less than his all for Hibs. Signed in the summer of 2019, he scored 18 goals in all competitions before the SPFL suspended the season because of the pandemic in March of 2020. Has scored a couple for Forrest Green Rovers since his January move. Photo: Ian MacNicol