Dear Mr. Fantasy: Getting a jump on '09

You can e-mail your Fantasy Baseball questions to DMFantasyBaseball@cbs.com. Be sure to put Dear Mr. Fantasy in the subject field. Please include your full name, hometown and state.

Nothing gets Mr. Fantasy cranky faster than a wrongfully overturned trade.

You've read about it before -- maybe even more than you'd like. Team A gets something it needs by offering Team B something it needs. The two owners come away happy and content, their teams improved, until the rest of the league's owners, resenting that two of their competitors outmaneuvered them, fight back the cheapest way they know how, by overturning the trade.

Mr. Fantasy doesn't like that. He gets angry and then takes it out on me.

So I tend to err on the side of caution, encouraging free trade and condemning those who try to interrupt it. But that doesn't mean I've totally lost my ability to discern, blindly subscribing to Mr. Fantasy's ideals. I'd like to think I can still recognize and point out an exception when necessary.

I'd like to think ...

I am in a 12-team non-keeper Head-to-Head league and was under the impression that our trade deadline was the same as the MLB's, but a trade just went down that many members found suspicious. They objected, but to no avail. Team A, which has a 13-7 record and the most points in the league, offered Jay Bruce and George Sherrill to Team B, which has a 7-13 record and the second-fewest points in the league, for Jason Bay. Closers and starters earn similar points in this league, but can you see a reason this trade might benefit Team B? -- Ed O'Boyle

SW: Assuming this trade took place after the Orioles placed Sherrill on the DL, then I agree with you without question: An out-of-contention team has no business making this trade in a non-keeper league. I could understand it in a keeper league because of Bruce's upside, but for this season, his numbers don't even put him in the same stratosphere as Bay, who right now looks like a legitimate Fantasy stud.

But this question becomes much more interesting to a broader audience if we operate under the assumption that Sherrill never did go on the DL. Just in case someone out there can't quite wrap his head around that concept, let's just substitute Brandon Lyon for Sherrill.

You got that? The contender traded Lyon and Bruce for Bay.

To make sense of this deal, we first need to understand the value of a typical closer, which can vary based on a league's depth and scoring structure.

You already covered the impact of scoring structure, saying closers score as many points as starting pitchers, which only helps justify this trade. But even more importantly, do you play in a league so deep that not a single source of saves is available on the waiver wire? Hey, people need saves, and if this out-of-contention owner felt he could only get saves by making a trade, you almost have to let this one slide (though you'd think he'd hold out for a Jonathan Papelbon for Bay instead of settling for a scrub like Lyon).

But chances are this non-contender could find some source of saves on the waiver wire, especially with options like Fernando Rodney, Chris Perez, Aaron Heilman, Dan Wheeler and -- back to Sherrill for a second -- Jim Johnson emerging only recently. In that case, a non-contender has no business trading one of his studs to a contender in exchange for a so-so closer.

In fact, you could argue that a non-contender has no business trading with a contender at all. That's why most Fantasy leagues set trade deadlines for early August, when the contenders have clearly separated themselves from the non-contenders. A trade like this one can't possibly meet both team's needs because a non-contender in a single-season league inherently has no needs.

See? I'm not totally inflexible. But you can bet I'll hear about this tomorrow.

Each year in my Head-to-Head keeper league, we're allowed to make one of our free-agent pickups into a keeper for next season. This leaves me to decide between pickups Chris Davis, Justin Duchscherer, Jair Jurrjens, Mike Mussina and Jorge Campillo. The keepers already on my team are Alex Rodriguez, Miguel Tejada, Adam Dunn, Matt Holliday, Evan Longoria, and James Shields. Who do I pick? -- Justin Bobko, Massapequa, N.Y.

SW: When choosing between a few middle-round types like the ones you have listed here, you should pick the guy who you think will go earliest in drafts next year, regardless of position. If your league doesn't penalize hitters for strikeouts, I'd probably keep Davis as long as he maintains close to his current pace over the final six weeks. Otherwise, I'd lean a little more toward the 22-year-old Jurrjens, whose numbers other than win-loss record compare favorably to the rest of the bunch. Besides, you have to think the Braves will go into next season with a fortified starting lineup and bullpen, offering him a better supporting cast and more opportunities for victories.

I am in a 10-team Head-to-Head league. I have been starting Jason Bay, Pat Burrell and Shane Victorino (When healthy) pretty much all year. I picked up Vernon Wells off of waivers and stashed him while he was on the DL, and I also just received J.D. Drew via trade. Besides Bay, I am unsure which other two guys to use. It is hard to bench Burrell because when he is hot, he is up there with the best. Victorino brings a great mix of speed and power, but I can't keep Drew on the bench, and Wells, when healthy, is a top-20 outfielder. Help me for my playoff push! -- Bryan, Minneapolis

SW: I think you give Wells a little too much credit, Brian. He hit only .245 with 16 home runs last year and, before his injury this year, didn't look much better. He still has only a .783 OPS. Sure, he has the potential to perform as a top-20 outfielder again, but he doesn't look like one right now. As for Drew, you shouldn't get so high on him either. Yes, he had that monster June when he hit .337 with 12 home runs, but he's hitting only .236 with three home runs since. Based on his career track record, you can't expect another performance like he had in June. In short, don't get cute in the playoffs. Stick with the guys who got you there, especially when they clearly look like the best options you have.

We keep three guys, and I'm not sure who to keep after Ryan Howard and Carlos Quentin. It's down to B.J. Upton and Tim Lincecum. I almost always go with hitting over pitching, but Upton has been a major disappointment for me and Lincecum is dominating. Who is a better keeper? -- William King, New York

SW: I like the way you think, William. I almost always go with hitting over pitching too, which I've hopefully made clear over the last few weeks. But therein lies the problem. We gave ourselves an out clause by using the word almost. You make a valid point: Upton has disappointed this year, especially for a player with such an impressive pedigree. Even more importantly, he'll lose eligibility at second base next season, and as an outfielder, his numbers don't make him look particularly special. But if nothing else this season, he's proven he can still steal bases even when his other numbers suffer. If you play in a Rotisserie league, stolen bases matter just as much as home runs, so I'd keep Upton and hope he reverts back to hitting 25-30 home runs next season, which he very well could. Otherwise, I'd make an exception to the rule in this case and keep Lincecum just because of the difference in value. In a Head-to-Head league, Lincecum will probably go in the first five rounds while Upton might not go until Round 8 or 9. If you want Upton back, you can always draft him again. I can't say the same for Lincecum.

I'm in a keeper league, auction style, with a five-keeper maximum and an incremental increase of $5 per year for each year of contract. I stink in my league this year and, therefore, have been able to stash some prospects because I won't make playoffs. I need to know if I should invest a three-year contract in an unknown like Matt Wieters, who I got for $1, or older but established guys like Chad Billingsley ($3) and A.J. Burnett ($2)? -- Jason Brown, Springdale, Arkansas

SW: Forget Wieters. You can't commit $30 over the next three seasons to a 22-year-old who has yet to appear in a major-league game. And I don't worry so much about him ending up a bust as I do him falling short of his potential for the majority of that contract. In fact, three years might not give him enough time to break out at all. Look at Jay Bruce. Look at Alex Gordon. Look at Hunter Pence after all of his rookie hype. Look at Jeff Francoeur, who clearly still has a ways to go. Look at Carlos Quentin, who needed more than a full season to emerge as anything Fantasy-relevant. Clearly, you have to keep Billingsley. You call him "older," but he just turned 24. Already striking out more than a batter per inning, he could emerge as a perennial Cy Young candidate for the next 10 years. And as for the 31-year-old Burnett, I wouldn't give him a three-year contract, but I'd keep him next year for $7.

I am in a keeper league where the amount of players you keep depends on where you finish the season. The top five teams can keep up to six players, and the last seven can keep up to nine. You can also trade slots for players as well. The league scoring favors pitching, as 15 of the top 20 players are pitchers. I am in 10th place out of 12 and am looking to next year. Who should I keep of the following players? Should I keep all nine slots? I have Ryan Howard, Evan Longoria, Stephen Drew, Troy Tulowitzki, Jacoby Ellsbury, Jason Bay, David Price, Roy Oswalt, Matt Garza, Johnny Cueto and Clay Buchholz. -- Darren Cote, Auburn, Maine

SW: If you keep fewer than nine players, you'll obviously need extra picks in next year's draft to fill out your roster. Do you get those picks at the beginning of the draft or the end of the draft? Because if you don't get them until the end of the draft and have to fill out your roster with a handful of players who halfway belong on waivers, then why not keep the full nine? Assuming you get extra picks at the beginning of the draft, though, you probably want to keep only the players who'd go in the first nine rounds of a non-keeper league draft, meaning Howard, Bay and Longoria for sure. I'd probably include Oswalt and Ellsbury also. Maybe Drew. Start with those six and see if you can trade a slot or two for something else worth keeping.

I am in a 10-team mixed Head-to-Head league. Playoffs are coming up soon, and I need to decide what four guys to start out of Curtis Granderson, Adam Dunn, Milton Bradley, Brad Hawpe, Alex Rios, Chris B. Young, Chone Figgins and Chris Davis. I am currently starting Granderson, Dunn and Hawpe. I want to start Bradley because he produces when he plays, but he is always an injury risk. -- Joe Laukaitis, Philadelphia

SW: I think you have the first three players right -- especially Hawpe, who has MVP-type numbers since May, batting well over .300 with 18 home runs. You can easily eliminate Young and Figgins, who just don't have the numbers this season and might not even deserve roster spots in a league as shallow as yours. I also think you should avoid Bradley, whose recent string of injuries reached almost laughable proportions last week. He'd return only momentarily -- for a span of a few innings, sometimes -- before going down with something else, showing he either doesn't want to play, is a hypochondriac, or has the musculoskeletal structure of a 60-year-old woman. The choice comes down to Davis or Rios, and in the playoffs, I'd go with the more established Rios, who despite his disappointing season, doesn't have the potential to burn you the way the unproven Davis could. Besides, Davis has cooled off recently.

With this year ending, I am already thinking about next year's draft. I drafted Albert Pujols 10th overall for my first pick this year, but as I look over the points for the overall year, there are about eight other first baseman who come very close to matching his production. Is the first-base position turning into a second-round-or-later position, or should Pujols still be taken in the first round? -- Berry Scruggs

SW: I like your thought process, Berry, but without knowing your particular scoring format, I can't say I agree with you. In standard Head-to-Head leagues, Pujols ranks 17 points ahead of the second-best first baseman (Lance Berkman), 36 points ahead of the third-best first baseman (Aubrey Huff) and 93 points ahead of the 10th-best first baseman (Derrek Lee). Meanwhile, David Wright, the best third baseman, ranks 11 points ahead of the second-best third baseman (Huff), 46 points ahead of the third-best third baseman (Miguel Cabrera) and 67 points ahead of the 10th-best first baseman (Melvin Mora). Should we eliminate Wright from first-round consideration also? Granted, I probably wouldn't draft Pujols until the second half of the first round, but I wouldn't let him slip to Round 2. If nothing else, his consistency justifies the high pick.

You can e-mail your Fantasy Baseball questions to DMFantasyBaseball@cbs.com. Be sure to put Dear Mr. Fantasy in the subject field. Please include your full name, hometown and state.