Montgomery was born in Penrith, New South Wales, Australia, and attended Bangor Grammar School and Queen's University in Belfast, where he studied history and politics and edited the student magazine The Gown.
[2] Early in 1999 Montgomery stepped down from the Mirror Group CEO role after some well-publicised running disagreements with the boardroom and the non-executive chairman Sir Victor Blank, and after a period for the company described by some commentators as "crisis-hit".
The acquisition was made in partnership with the American private equity firm and media broker Veronis Suhler Stevenson, part-financed with credit loans.
[5] In 2012, Montgomery formed Local World Limited, and acquired a number of regional papers which were later sold to Trinity Mirror (now known as Reach plc),[6] with Montgomery going on to form a new company called National World.
In 2020, Montgomery's National World company bought JPIMedia, publisher of The Scotsman and The Yorkshire Post, in a £10m deal which also included many other local newspapers.