EDIT 11/15/2019: Jake is likely accepting the qualifying offer from the Twins and is off the market.
With Jameson Taillon out for 2020 and possible issues beyond should things go poorly with his recovery the Pirates need to fill the 5th man in the rotation in 2020 and beyond when Archer could possibly be let go.
Both Jake and Madison have been tendered Qualifying offers which dampens some interest in both. Giving either of them a four year deal and maybe an option would likely make it worth it unless there is a higher end draft pick you think you are likely to get.
Jake has had moderate success through his career looking more like a mid to back end rotation type. However Jake made some changes in 2019 had has looked a lot better.
In 2019 he posted a 10.8 SO/9, a 3.0 BB/9, 0.91 HR/9 and a 35% GB rate supports his 3.51 ERA and 1.208 WHIP. Now you could say he’s had some luck with his defense.. but his BABIP was .302 which is a bit worse than the rest of his career.
Given his previous track record of looking like a mid to back end type with a 3.95 ERA a 1.243 WHIP and other stats supporting this, his 2019 performance may be a fluke. This could pull down his contract. There is NO DOUBT he would improve the Pirates pitching staff even if he goes back to a mid to back end type. His last draw back is that he isn’t going to go deep into games. Often a five and out guy, if they can get him to be a six inning guy… bonus. Clearly we would want him.
It wouldn’t take a truck load of cash to get him. MLB:TR estimates a three year $51m deal, seems pretty reasonable. But a four year back loaded $65m $10m, $15m, $20m, $20m deal might do the trick. Add in two option years at $20million with $2.5M buy outs each year would give him a guaranteed $70m or up to $105m for the full six years. This would get him through his age 34 year or 36 year.
The back loaded deal is also handy because when the average salary for quality players goes up.. his $20m won’t be as big of a burden.
All in all, regardless of how long and how much they pay, Jake or Madison (or both) would go a very long way to making the rotation more than respectable.