Here is what I would do next offseason w/JV: Offer him 2 or 3 different contracts. The first would be a contract that is heavily front-loaded for the first half of it so, for example, 6 years, $$180MM, but the first 3 would be $40 MM and the last 3 would be 30, 20, and last, 10 MM in his final year. This would make him more desirable in any future trade scenario, even if he was to gradually decline. Of course, a "no trade clause" could not be in the contract. The second would also be 6 years, but include incentives that are heavily backloaded, including club option years for a 7th and 8th year, taking him to age 40. This is to take advantage of his brash confidence in pitching much like he is now, but when he is in his mid-late 30s.
If Justin really thinks/believes that he still will be able to throw FBs in the mid-high 90s late in games, when he is age 36-38, then offer him a contract that will reward him for being able to do so, but not if he can't anymore. Include a mid-contract year buyout as well, say $$20MM in year 4, when he will be age 36.
The last contract could be a much shorter, but eye-popping 3 year, $$100MM contract extension through '17, which would enable the Tigers to have him through what most likely would be their entire current window of WS opportunity, when their contracted core players being currently Anibal, Justin, Prince, and Miggy will all still mostly be in their primes, and the ballclub's elderly owner, Mike Ilitch, might still remain vertical and mostly lucid through age 87. Can't include any other desirable players who would/may need new contracts or extensions during this WS window, such as Avila, Fister, and maybe Jackson, or perhaps less likely to be retained, Scherzer, Porcello, Dirks, and Infante.
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