Getting this done shouldn't be a big priority, but if Woodruff is interested, why not? Early pitcher extensions are risky, but great value when it pays off, whether through keeping your franchise player (Bumgarner) or through trades (Quintana, Sale). Always hard to judge the shifting tides in the market, or make player comps, but the Quintana contract should be a decent baseline; 5 years, $26.5m guaranteed with two team options for $10.5m and $11.5m with $1m buyouts; the two option years being the only FA years. They will both have very similar service time by the end of this season (i.e very close to two years), but Quintana will have been 2 years younger at the time and will have had maybe 80-100 more innings pitched. Inflation and overall increase in payroll will make up for some of that. So leave some leeway for where the final figures would end up, so while it's not a guaranteed rate, it should be in the same (Or nearby) ballpark. To me that type of deal looks fine. Doesn't need to be great to be worth it (It's OK, if somewhat disappointing, even for a #5 type starter or good swing man), not a crippling amount of money if if he absolutely bombs, and if he's a #3 or better starter it will have been tremendous value both during the arbitration years and with the extra two years. Super 2 starters get paid a lot during the last two years of team control.