The opportune moment

Surely you’ve heard the phrase “the early bird gets the worm,” albeit maybe from your grandmother. A more contemporary example might come from Captain Jack Sparrow: “Wait until the opportune moment.” I normally dislike clichéd sayings, but for what I’m about to talk about, they hold true. The “opportune moment” is fast approaching in fantasy leagues.

Deadline day

Most trading deadlines are a month away — long enough that most fantasy owners aren’t rushing to make a trade but short enough that it is in the back of their minds. This is the time when the learned fantasy owner will strike.

Consider, for a moment, the day of the trading deadline in your league. If your league is competitive, chances are several of your buddies are making frantic phone calls to each other, milling over stats, and constantly checking the league’s home page. By the end of the day, several trades will have been made. The chances are also good that sometime in the next week, at least one of these guys will be kicking himself for making a trade that he now regrets. This guy, this year, will not be you.

Deadline deal

In the days leading up to the trade deadline, every owner should at least be talking to every other owner to see if their teams are trade-compatible. Let’s imagine that I have Jake Peavy, who has continued to dominate through July and the beginning of August. I have several other very good pitchers and am leading most of the pitching categories.

Now I’m looking for a big bat. Since I’m in the lead in pitching, chances are nearly every other team could use a pitcher like Peavy. As I’ve made it known that my pitchers are available, I’ve received several inquiries and a couple offers on Peavy, but haven’t traded him yet.

Deadline day comes, and I receive the expected phone calls from the guys who want Peavy. The guy who was offering Carlos Guillen three weeks ago is now offering David Ortiz. The guy who offered Troy Glaus during the All-Star break is now willing to part with Justin Morneau. I’m in the driver’s seat, and I can play with these guys as much as I want. I can tell each that I have a great offer from someone else, and I can continue to raise the price all day. And the best part is that if someone tries to “call my bluff”, I do actually have solid offers to fall back on. By 10:00 P.M., I’ve traded Peavy for Prince Fielder and Corey Hart.

Would you rather be the guy who gets exactly what he wants (maybe more), or the guy who has to compete and in the eleventh hour overpay to get what he needs?

I, personally, would rather be the former. Instead of waiting until Aug. 12 to get what I need, I’m doing it now. I’ve determined my team’s strengths and weaknesses and am acting accordingly. Let’s say I am the guy who needed Peavy. I would try to get him now instead of waiting a month. Troy Glaus wouldn’t be enough, but what if I up my offer to Curtis Granderson and Brad Lidge? I’d still feel like I was getting a good deal (depending upon my specific needs, of course), and it is significantly less than I would have to give up to get one of the best pitchers in the game at the deadline.

Exploitation by MLB GMs

There are some good examples of MLB general managers who have put this into practice.

By acting early (7/13/06), Washington Nationals general manager Jim Bowden was able to acquire Austin Kearns, Felipe Lopez and Ryan Wagner for Bill Bray and a collection of other riff-raff. If Bowden had waited until the end of the month, more teams would have been interested in the guys he got, possibly after losing out on other targets, and the price would have gone up significantly.

At the deadline, it cost the Dodgers prized prospect Joel Guzman to bring in Julio Lugo. The Cubs parted with Greg Maddux to get Cesar Izturis. For Xavier Nady, the Mets got Oliver Perez and Roberto Hernandez. Think the Nats got a good deal on Kearns and Guillen?

On July 13, 2005, the Red Sox got Chad Bradford for Jay Payton. At the deadline, the Mariners traded Jesse Foppert (and Yorvit Torrealba) for Randy Winn. Again, striking early helped them get a nice deal.

On June 24, 2004, the Houston Astros gave up Octavio Dotel and John Buck to get Carlos Beltran. There were no comparable players to Beltran traded at the deadline, but given that he received the largest contract in baseball just a few months after this trade, I have to think the Royals could have gotten a little more had they waited it out and played the game.

Of course, there were other factors at play for these major league teams (such as money), but I think you understand my point. By acting early, before your opponents even realize they might need a specific player, you will be able to get him without the competition.


Of course, the opposite of this holds true for big name players you would like to trade. If you want to trade, say, Jake Peavy and you’re not getting the types of offers you want right now, you could wait it out. As the deadline approaches, teams will get desperate, and the offers will get better. Play the offers off each other until you can get maximum value. Make sure, though, that the player you wait on isn’t due for a decline. By the time the deadline roles around, his value might be below even the seemingly sub-par offers you are receiving now.

The “opportune moment,” for your team, might not be right now. It all depends on circumstance. In one league, I have a number of good starting pitchers, but most have been unlucky so far, leaving me a few spots out of first in the pitching categories. Jake Peavy has been great, but Felix Hernandez, Tim Lincecum, Javier Vazquez, Wandy Rodriguez and Curt Schilling have been unlucky. I also have Kelvim Escobar, so I can afford to lose Peavy.

Retroactive Review: Ace
Looking back at some of Justin Verlander's most interesting moments.

I will unload Peavy for a hitter eventually, but I will probably wait it out a little longer. To propel myself a bit in the standings, I will take in a little more of Peavy’s excellence and then let the rest of my great—although not fantastic— pitchers carry me to the finish once I trade him.

Every situation is different, but if you plan accordingly, you will be fine.

Closing thoughts

By now you’ve probably determined what you need to win, or in a keeper league whether you’re playing for next year. Either way, now is the time to act. If you wait, you will give up more value than you would need to had you played the trading market intelligently. Have a clear plan in mind, and execute.

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