We can be a means to an end - guarantee him first team football where he can develop and perhaps put himself in the window for another move down the road. Very appealing for younger players.
By contrast, there are plenty of players who've gone to bigger clubs and achieved f**k all, languishing on the bench or in the reserves which has ultimately hurt their earning potential and chances of winning honours.
In the job world, would you move somewhere where you were a small fish in a large pond and risked being overlooked or go somewhere perhaps smaller but where you enjoyed responsibility and gained visibility -all of which can help your progression inside or outside the company.
Far from clear-cut IMO.