In my last article I talked about what to do when you find yourself out of the race and you’re ready to prepare for next year. This week we’ll address the flip side–what to do when you find yourself in contention in a keeper league and are looking for that extra push. The first thing you need to do is determine whether you are actually going for it and have a legitimate chance to win. Erik Siegrist discussed this issue in more depth earlier in the week, but the critical factor here is to know not just where you are in the standings, but also where you have the most opportunity to gain and lose. We’re going to assume that you’ve done that analysis and are ready to go for it. Here are some pointers to help you along with that process.

Go Big or Go Home

You’ve made the determination that you’ve got a chance to win this year, and you know that standing pat isn’t going to be enough to do it. To give yourself a real shot, you need to make significant improvements, and make the commitment to trading some of your best prospects and cheap keepers to do so. Don’t settle on making incremental improvements. Remember that your competition will be trading as well. A small upgrade will only help you keep pace. There’s a psychological aspect to this as well. If you’re already out front and then are on the receiving end of a big dump trade, it tends to discourage the opposition from trying to match your efforts. While it’s true that some teams can improve without trading and are sometimes better off by not trading, you’d obviously like to see fewer teams making the effort.

Remember that you’re selling off part of your future to win this year. Make sure it’s worth the cost.

Make a Surgical Strike

Unlike earlier in the year, it’s time to focus on your specific needs, rather than trade just for pure value. Getting present value isn’t the question here–after all, you’re looking to be trading prospects and cheap-salaried young players in return for players that are going to put you over the top, and they won’t necessarily set you up well for the future. You don’t have an infinite number of opportunities to improve here, so make it count. Focus first on categorical needs and then positional needs. If the one category where you can improve is stolen bases, then trading Matt Cain for Mark Teixeira because your current first baseman is Travis Lee doesn’t necessarily address your needs. While in most cases it’s a good trade in terms of trading off future value for present value, if Cain is your best trading chit you’ve now lost the opportunity to trade for what you need. The exception here is if the only way you can trade for the speed guy that you need is if you trade one of your current sluggers, because all the top speed guys are on teams that are not dumping. Then adding Teixeira to replace the slugger that you’re moving to get that speedster makes a lot of sense.

Lather, Rinse, Repeat–Trade Pitching Prospects

My favorite keeper league tactic of all time is to acquire pitching prospects and flip them for present value with teams that are playing for the future. This applies for pitchers still in the minors, but it’s especially effective with those pitchers recently recalled from the minors. If your league’s rules allow for you to pick up that rookie pitcher and then stash him away on your reserve roster, all the better. If that pitcher has been on a great run in the minors and then is successful in his first handful of major league starts, you’ll have a potential gold mine on your hands. There’s a risk that you could be trading away the next Dontrelle Willis, but for every Willis there are three J.P. Howell‘s. That’s not to say Howell won’t pan out eventually, but it’s going to take some time, and by the time he’s reaching his potential, his new owner often has already lost patience with him, or he’s no longer so inexpensive as to make him a great roto bargain.

The best part about this tactic? Pitching prospects are virtually a renewable resource, both at the draft as well as in season. Take a quick look at the concentration of pitchers drafted in the early rounds of the MLB Entry Draft each year–it’s not hard to pick out a few high-profile names each year in the ultra rounds of your draft. Even if you missed out on taking a flier on a few of these pitchers in the draft, don’t fret, there’s still plenty of high-profile pitching prospects that will make the majors in a given year that you can pick up in order to trade. The RotoWire Staff Keeper League is an 18-team, 40-man roster league that allows you to reserve 10 slots for minor leaguers. The top hitting prospects are fairly well picked over, but the pitching talent that slips through each year is noteworthy. Among the top prospects that went undrafted in the Staff League and matriculated to the majors include Howell, Jason Vargas, Scott Olsen and Chris Ray.

Don’t Forget the Spare Change

After you’ve made your first big trade or two, your competition is likely to react accordingly. Don’t rest on your laurels with your initial trades–this title isn’t going to come easily, and you should be willing to go all out to win the crown. Don’t let that “one last good keeper” be the difference between first place and second place. It’s tempting to leave something in reserve for the future; not only do “Flags Fly Forever” (yes, I do pay Joe Sheehan a royalty each time I borrow his phrase), but it’s far easier to reload in most keeper leagues than it would be in real life.

Help Yourself, Hurt the Competition

While the primary focus here is to position yourself vis-à-vis those teams dumping for next year, there’s another type of trade you can make to lift yourself into first in categorical leagues. The mark of a truly artistic trade is one where you can shore up a weakness, trade a surplus, and then trade that surplus to a team that can subsequently pass up your main rivals. This happens most frequently when you can trade saves or stolen bases to a non-contender that has room to improve. This is a zero-sum game–lowering your rival’s overall point total is just as effective as increasing yours.

Quick Programming Note

RotoWire’s fantasy baseball radio show on XM Satellite Radio has moved time slots. Chris Liss and I are now on at noon in the east, 9:00 a.m. in the west, Monday-Friday. It’s still on Channel 175, MLB Home Plate. Make sure to tune in–BP’s Joe Sheehan, Will Carroll and Jonah Keri are regular guests, and we’ve had other BP authors on as well.

Jeff Erickson is the senior editor at Rotowire, and the host of XM Radio’s “Fantasy Focus,” heard every weekday at 9 a.m. PT (12 p.m. ET) on XM Channel 175. He can be reached here.

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