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Inside the GM's office: Anatomy of a deadline deal

For 13 seasons, from 1995 through 2007, Terry Ryan was the Minnesota Twins' general manager, a front-office executive who helped build the club into baseball's model small-market franchise. Limited by his tight payroll budget and owner Carl Pohlad's reluctance to spend freely for free agents, Ryan nevertheless navigated the Twins to four postseason appearances in five years from 2002 to 2006. The team's farm system -- which he developed along with predecessor Andy MacPhail -- is its strength and Ryan's legacy.

But the grind of the job got to him last summer, to the point that he announced his resignation last September, 13 years to the day after he got the GM job. And few things were more grinding for him and baseball's 29 other general managers than the days leading up to, and through, the annual trading deadline.

This week, as Thursday's deadline fast approached, Ryan -- who remains a Twins senior adviser and scout -- spoke with SI.com's Steve Aschburner about the process and the pressures of pulling off a deadline deal. Or at least, trying to:

As your season evolves and you get to around mid-July, you have a feel for where your team is headed. If you're in this thing -- that's one way. Or if you're not -- that's the other. So as you go through July, you're thinking about the possibilities for what you might want to do and what you can or can't do. A lot of this, you laid the groundwork for months ago, talking to another general manager maybe back in spring training. Believe me, GMs don't forget about those types of conversations. They take very copious notes.

Ironically, what you do this week -- what your team does, on the field -- really is big. They say all 162 games are important but the ones you're playing right now, the holes you see and want to fill, is what a lot of us react to. It's unbelievable. You lose a game here or there and you see where your ball club needs help. Injuries create situations that certainly have an effect on what you're doing and how your team plays over the next two months.

As a general manager, you have to have all the information you can. How long is someone going to be out? What's the wild-card situation? Who are we fighting? Who has what we need? What are we willing to give up?

Everyone pretty much knows who the buyers and sellers are going to be as the deadline gets closer. You know it from the standings, but a lot of times it depends on who you are and what your payroll is. Sometimes you can replace guys you give up through free agency and sometimes you can't. So your sellers are trying to rebuild, and your buyers are trying to go for it now. You see a deal between the Yankees and the Pirates, yeah, that makes sense. Everyone understands the philosophies there.

There are GMs who will go for it consistently at this time of year. Some guys are more aggressive, even if you wouldn't otherwise think they'd be buying. It depends on the philosophy of the general managers and their organization.

Where it gets tough is when you're in the middle somewhere and it's not clear yet which way your ball club is headed. You have to use your judgment and trust your instincts, and a lot of times, if you think your team isn't going to compete for the postseason, you shift into seller mode even though your fans want you to be a buyer. A guy like Ron Schueler took a tremendous amount of heat in 1997 when he was in Chicago. He didn't see it happening for the White Sox and he pulled the trigger on a deal. That trade with the Giants paid off for them down the road but I'm sure it was tough on Schueler at the time.

As more articles and information come out about prospects, fans get very excited about those guys in the farm system. The "future." Fifteen years ago, you never used to get that information but now people hear about players who supposedly are going to be stars or Hall of Famers when they're still down in the minor leagues. That guy takes on a life of his own before he's even ready to be brought up, what with all the blogs and other media.

We have more information than the fans and always have, but scouting is much more detailed and thorough now. So you're not going to pull too many surprises out of a trade.

As for the agents, as big a role as they play in our game now, at the trading deadline -- unless a guy's got a no-trade clause -- they're just not a factor. If he's got it, then you've got to get clearance and the agent is involved. When you get to these types of deadlines, it seems like there always are going to be players like that, with the no-trade clause. But I'd say mostly they're a non-factor.

I've been asked how risky these moves are, and whether you worry about trading away the next John Smoltz -- the Tigers traded him to Atlanta for Doyle Alexander, actually in an August deal, in 1987 -- or some other young player who becomes a star for 15 or 20 years, all for a quick fix now. Most general managers don't let that bother them. If they get what they want out of the deal, they're glad to make it. As long as you're satisfied that you did your homework, you evaluate your team and you know what you need, most GMs aren't going to worry about what happens five, 10, 15 years from now. Don't forget, Alexander went 9-0 to help the Tigers reach the playoffs against us. And, to be honest, a lot of GMs aren't going to be around 10 or 15 years later to hear about it.

It sounds like hot air, but you really do want both sides to feel good about a trade. You don't want to burn the other team, however, you might do that. You want to have some integrity. The relationships of the general managers is, I won't say close across the board but it is 'gentlemanly.' You want to be able to come back to that guy, pick up the phone again next week or next month.

One thing you learn is that, even though this is a people business at this level, you have to talk to the other 29 general managers whether you happen to get along with them or not. You never want to close an option, no matter what happens in your conversations or has happened in the past. Even if you feel like somebody hasn't been on the up-and-up or hasn't been totally ethical, you still have to deal with him.

It's like dealing with agents. You might have a bad experience with one, but you've got to stay positive. It's probably going to come around where you need to deal with that person again and you've got to do what's right by your ball club. Now, there are comfort levels with various GMs, some who you're very enthused to talk to and you're eager to pick up the phone. There are other ones you don't have much of a comfort level with. Just like any other business. Sometimes you feel good about dealing with someone, sometimes there's a little tension when you talk. But not too often -- usually with GMs, you have a relationship. Sometimes it's five years, sometimes it's 20 years.

Personally, I've never run across anyone I wouldn't normally deal with and only did so because of my job. It wouldn't do a GM any good to go through trade talks and not be ethical. That type of thing comes back at you. The word would get out.

It gets a little hectic, especially the last day. There are a lot of people involved in these decisions. We all want to hear what our scouts have to say. We all want to talk with our managers, and sometimes your owners get involved. But ultimately, it's the decision of the general managers and things do get kind of dicey when you're feeling that responsibility.

If you keep in your mind what it is you want and what you're willing to part with, you'll be all right. You're not going to make a panic decision -- you don't want to -- and you try to stay calm and cool. But as that clock is ticking down...

At this point, within your organization, you're meeting face-to-face with most of your people. Your scouts, your scouting director. You're in your office or in a board room and then, once your game starts, you go watch the games together. You're on the phone a lot now, never with everybody but probably with 10 or even 15 teams that you might have a match with.

There's not a lot of shooting the breeze. Most general managers have relationships with each other, so you don't have to spend time schmoozing anybody. I heard where [former Mets GM] Steve Phillips said they're short conversations -- names of players, then yes or no -- and you get that a lot. You usually get on there and get off of there. Steve was one guy who was always very aggressive. He knew what he wanted, he knew what he was willing to give up -- he was very good. Depending on your history with a guy, you know how he operates. Now there are a lot of new GMs, so it takes a little while to get to know their style.

You always like to get the guy who makes the decisions. Some teams, the GM has to take everything back to his owner. It's like working with a car salesman, where he has to go to his "sales manager" with your counter-offer. That can get very frustrating. It always takes more time, that's for sure.

You can have a deal, have a deal, have a deal -- and then you find out you don't have a deal. Suddenly a club will go in a different direction because they find something they think is better. That's when it gets discouraging. But you can't get mad. They have a job to do just like you do. All you can do is try to have other options, which is why you might be talking to five teams right up to the deadline instead of just two or three. You never want to be dealing with just one team, because of that.

While all this is going on, you're thinking about your players. They hear the talk shows, they read the papers and the Web sites. Some guys don't care when their names are out there. Some guys don't want to know. But there are some guys who let it have an effect on them. Which is too bad, because -- and I tell them this, if they're interested -- historically at the trade deadline there aren't too many players who end up moving. We've got 30 teams now and there aren't that many deals in any one year.

The technology has changed the way we work right up to the deadline. You really don't want to be on the road the week leading up to it, but if we were, we'd all leave phone numbers with the commissioner's office for anyone that needed to get hold of us. Now we don't have to do that. With text messaging, with e-mails, you can get in touch with people a lot more quickly.

The more you do it, the more you get comfortable with the whole process. But I don't know if you necessarily get better at it, because so many parts of it are out of your control. I was never a wheeler-dealer type. The Shannon Stewart trade [with Toronto in July 2003 for Bobby Kielty] really jump-started us one year. But last year, I was criticized tremendously for trading away Luis Castilla [to the Mets for farmhands Dustin Martin and Drew Butera]. I was trying to make our club better, and a lot of people didn't think I did.

No one works harder to improve a ball club than the general managers. Most of the time, they know who's available and who isn't, what's possible and what isn't. But there are times when something breaks late and an opposing GM can only say, "That's a heckuva deal." Then, sometimes, a year later, it doesn't look so good. Or you're criticized for a deal that, a year later, makes you look pretty smart.

Once a trade is done, the logistics of getting the player to your team, you have to make sure everything is in order. But all those steps -- anything medical, the transportation -- it's not as dramatic as it used to be, back when the rules said you had to have the player in your city by the deadline. There used to be a safety factor, back 10 or 15 years ago, where you had to get the guy on a plane or on the road and rush him to your city. It was a little odd, I always thought. Now you don't have to do that anymore, as long as the deal is finalized and the player is on board and the paperwork has been filed.

People sometimes think this is like April 15 for a tax accountant, where you can exhale and relax a little after the trade deadline has passed. In fact, the month of August, there's still plenty of work. You can still make trades -- and you might have very impactful trades -- only now you have to deal with the waiver process. It's very difficult to get a player through waivers and it's getting tougher. A lot of GMs just don't like to let players clear waivers. That used to be less of a problem, because some teams didn't want to take on a player's contract. But the game is healthy enough now, with attendance up and revenue-sharing, that teams are better able to handle the bigger payrolls. Look at the Twins, who are considered a smaller market. We always have to look at payroll. But we're "healthy" now. We're not losing money. I can't speak for the other teams, but that seems to be the case in a lot of markets now. Teams are healthy [financially] and many of them are more willing to spend. (Don't get the wrong idea; our payroll is $20 million less than it was last year, with [Torii] Hunter and [Johan] Santana gone.

Sometimes you're going to have a September trade but, really, you might see a young guy who comes up [from the minors] and makes a terrific impression. But the stuff within your own system, that's ongoing. You're focused on that from the first day of spring training to the end of the season. By September, most of the time, you are who you are.

This is the first time in a long time that I'm not "the guy" at the trade deadline. I'm involved enough where I'm certainly a part of this, but not to where I'm on 24-hour call. It's nice at last, because I'll be honest with you, I had zero life. I still watch an awful lot of baseball. But when you've been doing the same thing for 13 years -- you have the same things, the same days -- this is a nice change.

Steve Aschburner covered the Minnesota Timberwolves and the NBA for 13 seasons for the Minneapolis Star Tribune. He has served as president or vice president of the Professional Basketball Writers Association since 2005. His new book, The Good, the Bad & the Ugly: Minnesota Twins, can be orderedhere.

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