How I would approach it:
First I would offer Jon Lester a 6 year deal. Born: January 7, 1984. 31 at the start of the deal. I would front load it to free up the back end if they need to trade him during the end of it.
Clayton Kershaw: 15:$30M, 16:$32M, 17:$33M, 18:$33M, 19:$32M, 20:$33M That is top end cash.
Zack Greinke: 14:$24M, 15:$23M, 16:$24M, 17:$23M, 18:$24M is the bottom end.
That is how much TOR are going for.
If they started him out at 30 mil for 3 then 25 for 2 then 20 for the last year he comes in at 6 years 160 mil. If he wants more then give it as a signing bonus.
After that I would run Arrieta as my 2. On a 3 I would start with Hendricks. Now this is when I would roll the dice on a risk F/A at a buy low.
Chad Billingsley
Billingsley, who suffered the injury while recovering from Tommy John elbow reconstruction, said he opted for another surgery over stem-cell injection therapy after meeting with surgeon Neal El Attrache, based on a risk-reward comparison. A former All-Star, he hasn't pitched for the Dodgers since April 15, 2013. The flexor tendon surgery is less invasive than Tommy John reconstruction. Billingsley said he will rehab for three months, start throwing in December and be ready for next Spring Training.
I would offer him a 5 mil with performance options. I would let him take his time and when the ASG rolls around get him ready for the postseason. At that point they can take the weakest link in the rotation and sell or push to the pen. (If they are in it but I'm feeling that they have a opportunity next year if the Rooks can play)