Even considering the 1899 scheme, I fail to see how he came in for a quick profit. The tax bill and wages alone will have put him 7 figures in the red with no hope of recouping that back.
Additionally, He has openly said his pockets aren’t deep for a football club owner, that’s no secret.
Perhaps he underestimated the job/debts when he purchased the club. After all, something deterred Elliot’s consortium after their bid was initially accepted.