5 – Michael Bostwick
Peterborough United’s reigning Player of the Year dropped a division to join us in July 2017, with Michael Bostwick arriving for an undisclosed fee after 228 appearances for Posh. He added the EFL Trophy and League Two title to an already substantial collection of honours, winning our Player of the Season award in the title campaign. Burton Albion signed him after his departure in 2020, and further promotions followed with Stevenage and Boston United before spells at St Albans City and Bourne Town.
It feels fitting that Michael Bostwick and Harry Anderson are close together, given that they arrived permanently from Peterborough in the same deal, but Bozzy was the signing that really made you sit up and take notice. Here was an established League One footballer dropping into League Two, and it was difficult to imagine a player better suited to what Danny and Nicky wanted to build.
There was a financial commitment and considerable expectation, but relatively little doubt about his ability, which is one reason he falls just outside my top three: this wasn’t an overlooked prospect we developed into something nobody had anticipated. We knew he was a phenomenal footballer, and he delivered on that reputation with performances that made him an enormous figure in our success. Big signings can end up on the wrong sort of list simply because they struggle to justify the expectations attached to them, but Bozzy embraced that responsibility.
We didn’t make money when he left, yet in terms of the statement his arrival made and the contribution that followed, he remains one of the best signings we have secured.
Hard to argue with the list … totally agree with comments about Harry Anderson !