I wanted to start this post by clarifying how I go about determining whether a guy is a worthy keeper or not. It's essentially just a matter of projections. I look at how I expect the player to perform next season, and measure each of their five relevant statistics, and whether that player will have a positive, neutral, or negative effect on that statistic.
For example, Juan Pierre projects to have at least 40 steals next year, which is a positive. While he's a career .300 hitter, he's hit .292, .293, and .283 over the past three years, so something more like .285 is reasonable to expect, which makes batting average a neutral statistic. Finally, he averages about 1 HR every 100 games, so home runs is a strongly negative statistic. I take that combination of positives and negatives and weigh it against other options at the same position, and decide if the player warrants being declared one of the 80 best fantasy players (96 players are actually kept, but in order to declare someone a keeper, you should feel better than "just barely made the list").
The very last thing I look for is how I expect them to perform beyond next season. Listen, if you don't think you're going to get anything out of a player this year, they're just not a keeper. The rare exceptions would be if one of the elite young hitters (Pujols, Cabrera, Holliday) were to get injured in the offseason and be expected to miss a majority of the upcoming season. You would keep that player based on future performance, but only after they've proven that they're an elite hitter.
To me, you don't keep a pitcher who's expected to miss major time, regardless of how good they've been. Pitchers are much more susceptible to the "career-threatening injury" than hitters, and it often takes them several years to fully recover and regain their form. Draft them in the middle rounds if you like, but I say let other people have a crack at them first. You don't want a Mark Prior situation crippling your team for years to come. (Trust me, you don't).
Now, on to Jon Lester. First things first, Lester is a cancer survivor. Regardless of his baseball prowess, it's nice to know that sometimes cancer doesn't kill people. I have a friend who has battled cancer and won as well, so it's nice to see that humanity is at least picking up a few wins against the big C. Because the big C is a fucker. Fuck him.
It turns out, though, that Lester actually does have some baseball prowess. He had a nice 2008 season, picking up 16 wins and posting solid averages and a decent strikeout rate in his first full season in the majors. He also had a good enough postseason that all of the baseball media declared him an "ace in the making," shrugging aside Josh Beckett and his absurd postseason numbers. While I don't think Lester is better than Beckett, he's obviously got some skills.
Lester will also be only 25 next season, and could make strides forward again this season. He plays in Boston, which means he should fall backwards into 15 wins every year, even if he doesn't get any better. While you'd like to see better strikeout numbers from a keeper pitcher, Lester's upside is undeniable. I expected to say no when I started this article, but I'm going to say that, although he's borderline, Jon Lester is a keeper going into 2009.
Projected stats: 18-10, 3.30 ERA, 1.25 WHIP, 180 Ks
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