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When Should A Team Make A 'Win-Now' Trade?

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We're familiar with the sell-off trades. We don't like what causes them. When should a team pull off the other types of trades?

The Cubs traded Jeff Samardzija In 2014. Will they trade prospects for a veteran In 2015?
The Cubs traded Jeff Samardzija In 2014. Will they trade prospects for a veteran In 2015?
Ed Szczepanski-USA TODAY Sports

Sean Marshall for Travis Wood. Matt Garza for three minor league pitchers and a minor league third baseman. Scott Feldman for two struggling pitchers who were out of options. Jeff Samardzija and Jason Hammel for three guys in the minors and a PTBNL. Yeh, we're all tired of the premise. Theo Epstein claims the goal is to win the division in 2015. We want the trades the Cubs make in 2015 to be ones to improve the team toward the post-season. However, are all aggressive trades good?

If you ask a fan of the Oakland Athletics, they probably aren't too keen on either of their two major trades. In Addison Russell and Billy McKinney, they gave up their two best prospects, and Yoenis Cespedes was close to their best hitter in the majors. Now, they have mortgaged their present and future for a one-game showdown with the Kansas City Royals that they lost.

This will actually be a bit of a group project. I want to come up with a list of questions. I already have a number of them. By no means is it an all-inclusive list. I want to come up with a sufficient battery of questions 'before the fact' so we can lay some ground work as far as deciding if a "gamble trade" near the deadline, or even in the off-season, is a good one.

I can see some of your eyes rolling already. After all, all I care about is the minors. Not true. If there were a healthy dozen people other than me with steady and accurate reports from the minor league games, I wouldn't have a need to listen. I could, instead, read the wraps from the droves of people committed to going in-depth on the games from Myrtle Beach, South Bend, and Eugene. Josh does a great job at the recaps, and I couldn't do it as well as he does. However, it's tough to focus on more than one game at once. Sometimes, more than four are going at one time.

I look forward to when the progression becomes natural. I cover the minor leagues from April until early September, then I switch seamlessly into listening to games that Jake Arrieta isn't starting. All the way through the post-season. To get there, players in the minor leagues will be dealt. It will sting, but it will be necessary.

My aim is to string questions together in advance to decide if trades yet to be announced are good ideas. Not all trades make sense. Not all appear foolish. The hope is to get the most "trade all the prospects" type and the "trade for all the prospect" type to realize there is wiggle room, but also some edging on the gray in the middle.

All are Yes or No questions.

1. Is another team in the division clearly better than yours?

2. Will there be a team next year who figures to be clearly better than yours?

3. Does your competitive window have some years remaining?

4. Is money going to be under control in the near future?

5. Is the main outgoing piece among your five best prospects?

6. Is the main returning piece a short-term solution?

7. Does the main outgoing piece represent as a top-of-the-rotation starter or top-five-in-the-order hitter?

8. If the main incoming piece has a standard rest-of-the-year, will your team be underdogs in the division?

9. Are you outside the top three teams in the league before the trade?

10. If the trade backfires, could it be a team-breaking move?

As you can tell, the more Yes answers, the more dangerous the trade looks. The more likely the trade only nets a wild-card finish, the less likely a trade should be made. However, if it's a piece that really isn't that big of a system loss, than rolling the dice might be a good idea.

Oakland, Milwaukee, and Atlanta were all in good shape for the post-season much of the 2014 season. They all made trades to try to improve. Some were major. The Brewers and Braves opted for minor moves. The Dodgers didn't fix up their bullpen very much, and it took less than seven innings in the postseason to realize they should have.

It isn't an "always yes" or "always no" on either side. I'm sure the Dodgers tried to upgrade their bullpen, with opposing front offices wanting Joc Pederson or Julio Urias in exchange. That something wasn't done isn't a sign that nothing was tried.

I'm sure some of you can add questions to my list. Ten seemed sufficient for now. If the questions elicit seven or more Yes answers, it might be a bad idea. If it's closer to two or three Yes answers, it's probably safe to pull the trigger. As we get toward July 2015 (Don't worry. There probably won't be any major trades before then, even though there probably should be), we will be on one side or the other of some trades. Or like this time around, both sides. (Jacob Turner, anyone?)

When the time comes, if it is a severe stretch to see the Cubs competing for the division title, I will probably be in favor of mild talent purge in July. Whether the team plays at a .380 winning percentage or at .430 or .470, the likelihood of making a winning run with a losing record like that isn't that strong. In that instance, if a Pedro Strop, Chris Coghlan, or a starting pitcher on a short-term deal, then by all means, trade him for a quality return.

However, if the Cubs are legitimately in the hunt, I'd have no problem parting with a quality prospect, as long as the answer isn't Yes too often.