The prevailing narrative here is that the team was actively looking to lose to acquire draft picks. Hugh Jackson was extremely good at losing, so he stayed.
The owner of the Cleveland Browns uses the team to generate more revenue. For NFL teams, performance has little to do with their value or ability to generate additional revenue.
There is no strong financial incentive to win in the NFL, aside from the owner's ego. The Browns' owner's ego is driven by money, and the result shows on the field.
From doing more research about this, it seems they don't want to use the good draft picks, but to sell them on to teams that do want to win.
The draft pick is itself a commodity that can be traded*, so by losing they get a premium commodity, that they can sell on, and by selling their picks they ensure that they continue to lose to get the valuable commodity.
The owner of the Cleveland Browns uses the team to generate more revenue. For NFL teams, performance has little to do with their value or ability to generate additional revenue.
There is no strong financial incentive to win in the NFL, aside from the owner's ego. The Browns' owner's ego is driven by money, and the result shows on the field.