Gamble tomorrow for today? That's the decision GM's must make

E-mail question from John: "Are the Phillies really not going to trade for Roy Halladay because of Kyle Drabek? Kyle (bleeping) Drabek? Who the (bleep) is Kyle Drabek? I don't care if Kyle Drabek goes on to win 500 (bleeping) games ... how can you not trade for Roy Halladay?"

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For years now, I've never understood the expression "You can't have your cake and eat it, too." My mother used to say that to me all the time, and I always wondered what does that mean? If you eat your cake, you have it. If you have your cake, you eat it. It makes no sense. Looking back now, I think the expression should be: You can't have John Smoltz and win it, too. That makes sense to me.

You already know that I'm talking about what is probably the most famous today-for-tomorrow trade in baseball history. In 1987 the Detroit Tigers were in a heated pennant race with Toronto. It became clear at some point that unless the Tigers got another pitcher, and fast, there would be no way they could win the American League East.

So they traded Smoltz to Atlanta for a veteran pitcher named Doyle Alexander. When they made the move, there was a whiff of desperation about it. Alexander was almost 37 years old. He had not pitched particularly well for almost two years. He had played for eight teams in his Magellan-like career, and he played for the Yankees twice. On top of that, he was not exactly known for his clutch pitching*. There were a lot of reasons to think that Alexander would not be much of a factor.

*Alexander's postseason numbers were abominable -- he was 0-3 with a 7.65 ERA in the playoffs and World Series. And that year in the playoffs, he would get bombed in both his starts.

Instead, he was THE factor. Alexander was great -- in the regular season at least. He started 11 times in the final month and a half as Detroit and Toronto went back and forth in the standings. And ... Detroit won all 11 times he started. It was remarkable. He threw three complete-game shutouts. He punched up a 1.53 ERA. On Sept. 27, with the Tigers 2 1/2 games behind Toronto, he threw 10 2/3 innings and gave up only one earned run to beat the Blue Jays. His next start, he beat the Jays again to push the Tigers into first place to stay.

It was one of the greatest pennant race performances in the history of the game. You never want to give too much credit to one player, but Detroit won the American League East in 1987 because of the Doyle Alexander trade. There was much joy in Detroit. Then the Tigers lost the ALCS to Minnesota in five games.

Meanwhile, Smoltz went on to win 210 games and saved 154 more for the Braves and has been one of the most successful postseason pitchers ever. He's going to the Hall of Fame someday.

And there's your question, the one that hits every baseball trade deadline, the one that today is larger than ever before: Is it worth trading away a potential superstar for a chance to win right now? Or -- as John and others say -- "How can you not trade (bleeping) Kyle Drabek for (bleeping) Roy Halladay?"

It's a multi-layered question. For one thing, there's the uncertain future of great prospects. Many of them -- most of them -- do not pan out. Injuries. Adjustment issues. An inability to handle the daily grind. There are a lot of reasons.

Whatever. Take a look at Baseball America's Top 10 prospects from 10 years ago:

1. J.D. Drew2. Rick Ankiel (as a pitcher)3. Eric Chavez4. Bruce Chen5. Brad Penny6. Michael Barrett7. Ryan Anderson8. Pablo Ozuna9. Ruben Mateo10. Matt Clement

Now, looking back as a general manager, you would probably be willing to trade ANY of those players to get a year and a half of Roy Halladay. Drew has had a good but oddly uninspiring career so far (in part because of injuries), Ankiel is a struggling outfielder, Chavez has played just 121 total games the last three seasons. Bruce Chen is pitching in Kansas City now -- his TENTH team -- and he's 0-5 with a 6.39 ERA.

On the other hand, that same year the NEXT 10 prospects included: Roy Halladay himself, Lance Berkman and Carlos Beltran -- and trading any of those might set your team back 10 years. When these trades backfire, they BACKFIRE ...

Example 1: At the end of June in 2002, the Montreal Expos traded Grady Sizemore, Cliff Lee and Brandon Phillips for pitcher Bartolo Colon. At the time the Expos thought they were legit contenders. They were not ... they finished 19 games out of first and while it's not a direct cause-effect, they were out of Montreal three years later.

Example 2: At the end of August 1990, the Red Sox (already up 6 1/2 games in the division) felt like they needed to shore up their bullpen and so traded for reliever Larry Andersen. He pitched well down the stretch ... and a collapsing Red Sox team did manage to hold off the Blue Jays and win the division. But they traded New England native Jeff Bagwell, and Red Sox fans never quite got over it.

Example 3: Before last season, the Seattle Mariners, fresh off a fluky 88-win season, felt like they were one pitcher away from being a World Series contender. They traded for overpowering Orioles' lefty Erik Bedard. Unfortunately, Bedard got hurt and the Mariners were actually quite awful -- they would end up losing 101 games -- and the players they traded include blossoming star Adam Jones and effective closer George Sherill.

Yes, it's a high-risk game trading away prospects. And that has never been more true than it is now. For one thing, even big-money teams are looking to control costs. The Yankees team payroll is less now than it was in 2005. The Boston Red Sox payroll is less than it was in 2004. The Los Angeles Dodgers payroll is less than it was in 2001. There's a certain amount of restraint in the air when it comes to big-league payroll and having your own player under your control for six years at a discounted price is very appealing, even for the big spenders.

Second, teams invest more heavily than ever in their prospects. Take Kyle Drabek. The Phillies drafted him in the first round in 2006 and paid him a signing bonus of more than $1.5 million. He had Tommy John surgery the very next year and made only eight starts in the minor leagues in 2008. The Phillies has nurtured him, encouraged him, and paid him quite a lot of money. They are fully invested in him. Sure, Roy Halladay could make them the best team in baseball the next two years. But he also might not. And if Drabek goes on to become a big star, there will be a huge sense of loss.

Decisions. St. Louis decided to go for it -- the Cardinals traded away a package of prospects, including 23-year-old third baseman Brett Wallace, for Matt Holliday. The Cardinals are in the heart of the race, and they want someone to hit behind Albert Pujols, and so they closed their eyes and made the move. I suspect before the deadline hits, a team will pull the lever on Halladay and others ... it's just too tempting. But it's like one baseball executive told me: "The key in these deadline trades is not what you know about their player. It's what you know about your player. You have to be honest with yourself -- you can't get caught up in the hype and talk about potential. You can't fall in love with them.

"But if you are convinced that your player is going to be a star, then you hold on to him no matter what anyone says. They'll scream for a while. But they'll thank you in the morning."