I enjoy looking at the "similarity scores" section on a guy's baseball-reference.com page. I'm not a smart enough geek to claim how predictive they are, but on the surface, they often seem to be on target.
So for Cole, the most similar players at particular ages were Syndergaard (at age 22), Marichal (23), Millwood (24), Nola (25), McDowell (26), Millwood (27), and Strasburg (28).
The guys with the most similar stats through their age 28 season are Strasburg, Price, Santana, Weaver, Oswalt, Peavy, Hamels, Cueto, Hudson, Verlander.
Those are good players, but looking back at the careers of the seven guys who have passed age 35 (all but Strasburg, Price, and Cueto), in my opinion the only one who earned close to 7/$245MM money was Verlander. He pitched an average of 206 innings with a 5.0 WAR in those years.
As a group, those seven averaged only 158 innings and 2.9 WAR per season. Keep in mind that those are driven up by Verlander. There's an 86 percent chance you get an average of 150 innings and 2.6 WAR. And if you managed to get a Santana/Weaver/Oswalt/Peavy, you got 133 innings and a little less than 2.0 WAR.
And as a reference point, Odorizzi pitched 159 innings with a 3.6 WAR this year. Do we really want to pay $27 million for something less than Jake Odorizzi for the next seven years? I don't.