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Here is another way to look at the question of would you pay Cassel $10 million or $15 million for a one year deal if Brady was 50-50, and the one I suspect BB used.
If we knew 100% for certain Brady would not play this year would we sign Cassel to a one year $20 million or $30 million dollar deal?
The answer is no. Cassel is good but his not $30 million a year good. And that is basically what you would be paying if you paid $15 million with a 50-50chance he would play and 50-50 he would be collecting a pay check for holding a clipboard.
Now you're comparing apples to oranges, though—if it were 100% certain that Brady couldn't play, then franchising Cassel would be a $15M "guarantee," and not a "gamble" at all.
That said, I do agree that it's unlikely BB would pay $15M if the odds were only 50-50 or so.