He won the gamble.
I don't know that I agree he "won" the gamble. If you average out fWAR and rWAR for Jordan Zimmermann and David Price, Zimmerman was worth 5.1 WAR in 2014 and Price was worth 5.3 WAR. Zimmermann is a year younger.
Of course, David Price then had a 6.2 WAR season this year, while Jordan Zimmermann had a 3.3 WAR season. So Price is going to get $200 million or whatever and Zimmerman will get a little over half that.
I don't think there's a chance in hell Zimmermann didn't think a great year would get him less than $150-160 million. He just didn't have a great year. Obviously he didn't "lose" the gamble, but I think we can say he didn't "win" it either. He walked away from the table even, so hopefully he enjoyed some free drinks