Let's see. Sheffield is 32, with two more years to go on his current deal. Even though he is putting up some pretty good numbers, he is pretty much at the end of his long-contract period, and will be starting in on the year-to-year deals, or maybe 2-yrs.

Doesn't hurt to ask, though. I'd like a lifetime contract too.

If I were the Dodgers, I'd like have Sheff signed until the age of 38 or so. If they are fairly confident that he won't bolt, they can just offer 1 or 2 year contract extensions every time he enters his final year.

He wants to stay in LA. He is one of the very best hitters of his generation (he has played in many pitcher's parks). It's very likely that he'll still be a championship quality player at age 38, so in my book he's a good risk.

My guess is that he makes it. He needs to have a reasonably long career, though.

He hasn't had 14 full years.

14 years is not a long career for an outfielder.

Okay... we are playing word games here, so I will amend my comments to a "long career" - 2300+ games played.

And it is also not likely that he will hit HRs at his current pace, as he is past his peak and his rate ought to slow down quite a bit.