Major League Baseball

A behind-the-scenes look at the Ryan Howard contract

Published Apr. 30, 2010 1:00 a.m. ET

Ken Rosenthal

The debate over Ryan Howard’s new contract is not likely to subside anytime soon.

The five-year, $125 million extension was a stunner, and not simply because it happened without advance notice.

Howard, 30, already was under contract through next season, yet the Phillies - who host the Mets this weekend (Saturday, MLB on Fox, 3:10 p.m. ET) - still were willing to extend him through age 36.

The timing was so intriguing, I went straight to the negotiators – Phillies general manager Ruben Amaro Jr. and Howard’s agent, Casey Close – for further answers.

One thing quickly became apparent in those conversations – the Phillies place great trust in Howard, who has been in their organization for almost nine years.

Amaro is well aware that most players decline in their 30s. But the Phillies, perhaps more than most teams, value makeup. They clearly are not beholden to sabermetric thinking.

In fact, when I asked Amaro in a follow-up e-mail how he views RBIs – a statistic often downplayed by sabermetricians – he responded with a reply that is sure to send the numbers crowd into spasms of rage.

“The sabermetricians are welcome to have their opinions about our business; however, I choose to ignore their opinions,” Amaro said.

Well, Amaro is getting criticized for the Howard deal not just by sabermetricians, but also by rival executives.

I interviewed Amaro and Close on Wednesday in separate telephone conversations.

Q: When did the discussions start in earnest?

AMARO: I made a call to Casey probably sometime in the off-season, real early. I told him, timing-wise, I didn’t know if it was the right time to start talking about it. But maybe we could revisit it. We decided at some point before spring training to get together and talk. We had a brief conversation about maybe moving something forward. Shortly thereafter in spring training we started kicking things around a little bit more seriously.

CLOSE: Clearly, there has always been an interest from the club to get him on the books long-term. We were just never able to come to the right agreement for both parties. When I had a chance to visit Ruben in spring training, he basically made the initial salvo and said they’d really like to think about a way to get this done.

Q: When did you get optimistic it might happen?

AMARO: We were optimistic we could do something. We had put ourselves in a position and decided as an organization that we were going to do something longer term.

We felt as an organization, after having discussions internally, that we were comfortable with Ryan as a very big piece to our organization and one of our cornerstones, (going) further out (on the length of contract) than we probably would have done in prior years.

CLOSE: Initially, I wasn’t sure. There was so much resistance to the term. (But) the Phillies really wanted further clarity to the future of their franchise. They wanted to know where Ryan fit in not only financially, but also where his production would fit for the future performance of that club and in trying to keep that club together.

Once they guaranteed Ryan at least a five-year commitment moving forward, we got a little closer on where the overall dollars would be. I felt the deal at that point had a chance to materialize. It wasn’t going to happen until we got to that point.

It’s not easy to do a deal of this magnitude when neither side has to do the deal. That’s the real trick, the art of a deal like this, to reach consensus when there’s not a gun to either side’s head. The art of a deal like this is to work through some complicated issues without facing a natural deadline.

Q: Was it always going to be a five-year deal? What other frameworks were discussed?

AMARO: As you know, we like shorter deals. But there was a market that was kind of set for the more elite players in the game. There is some length to those deals. We started off at a three-year extension with a chance to get to four. We felt like after having further discussions internally, further discussions with Casey, that it was going to take longer than that.

There’s some discomfort with the length. But this is kind of what you have to do to keep your elite players. After discussing it internally, we felt that him playing at age 36 was not going to be as big a risk now as maybe it would have been a couple of years ago.

CLOSE: This was going to be Ryan’s big bite of the apple. (Five years) was where the ceiling was drawn as far as where they felt comfortable guaranteeing a deal at the age of 32. They wouldn’t go any further than that . . . They set five years as their absolute bar and really had to stretch to there, given the fact that it did take him all the way to the age of 37.

Q: Casey, did you ask for more than five?

CLOSE: Oh, yeah. Of course. We did. We initially searched for something that might be longer. That’s where the rubber hit the road, as they say, as far as what their bottom line would have been, the absolute maximum they would be stretched to.

In part, that was due to the fact that they were also staring at the two (remaining) years at $19 million and $20 million ahead of them. For them, even though it wasn’t a seven-year deal, it sure felt like a seven-year deal given the fact that all these years were going to happen after the age of 30.

Q: Ruben, why were you comfortable with the five-year term? Because of what Ryan has done? Because of the way he has gotten himself in shape and improved his defense?

AMARO: Yes. Frankly, he has dedicated himself to being a more complete player. That happened even after he signed the three-year deal (on Feb. 8, 2009). That gave us good reason to think he would continue to do that.

CLOSE: It really came from all of Ryan’s hard work, both in the weight room and at first base. He has really made himself more of a complete player. He’s taking extraordinary care of himself. They were much more comfortable with Ryan’s ability to age better, for him to continue to be productive past the ages of 32 and 33.

Q: Ruben, as you well know, there are several other prominent first basemen who are eligible for free agency after the 2011 season – the same class that would have included Ryan. You could have played it out. You could have waited and surveyed the market. Why didn’t you do that? Why did it have to be now?

AMARO: (Because of) the impact he has on our organization and the impact he has on our lineup. There is no guarantee that we could have ended with any of these free agents.

We know the person. We don’t know the other guys as well. We live with Ryan every day. We have a good feel for him as a person and as a player. Character means a lot to us. And he’s one of our own. As we’ve said before, if we have quality people, quality players, we’d like to keep ‘em. And we don’t have a problem paying for their production.

Q: How important is it to (team president) David Montgomery for the Phillies to keep their own?

AMARO: You pick and choose the right guys. It’s great as an organization for our fans to identify with players that we think are quality players and quality people. We’ve invested money in good character people and good athletes. They’ve proven to us they’re championship-caliber. We’ve won championships with them. We don’t have any reason to believe these guys will change.

There is a risk. You hope guys continue to play and continue to be the same person with a high level of character. But that’s part of the Basic Agreement. It’s not like the NFL. Once you sign these contracts, you live with them and go forward.

Could Ryan Howard not be as productive a player at 34-35-36 as he is right now? That’s a possibility. But based on how he’s gone about it, (it’s) for the same reason we did the extension on (Roy) Halladay – we had enough background on him as a player and as a person and as an athlete. We just felt like we were not taking as great a risk on him as we would be on other people.

Q: Ruben, you’ve seen David Ortiz. He has declined. (Alfonso) Soriano has declined. There are a lot of players who have declined in this age range, 32 to 36. What is about Ryan that makes you think he will be an exception?

AMARO: He’s dedicated to continuing to improve. Not that those other players weren’t, but I know based on how he was brought up, his family, the way he goes about his business, the risk is lower with him in our estimation because of the familiarity we have with him.

Is it possible his bat gets slower or he loses power? Is that a possibility? Sure it is. None of these decisions we make is a slam dunk.

CLOSE: You have to look at what Ryan has continued to do. Some of his numbers have been dictated by the change in the game itself – meaning, the shift. Some of his rates, his (batting) average, his on-base percentage, those have been specifically dictated by that shift. His power, his run production, those have remained remarkably consistent over the past four years.

What you’re seeing is Ryan’s ability to dedicate himself. He looks better today than he did three or four years ago. He’s moving better. He’s a very good athlete. He has taken away so much of the concern.

I’m not particularly worried about his performance. The really good players who are that consistent . . . look at Mo Vaughn, look at some of the players you named. Were they this consistent in their run production? No.

He, Griffey, Babe Ruth and Sammy Sosa are the only guys to (hit at least 40 homers and drive in at least 130 runs) over a four-year stretch. He plays a position at which players frankly age well. It’s not a particularly demanding position. And power has always naturally aged well. That’s what his No. 1 skill set is.

Q: Ruben, how much criticism did you expect for making this deal?

AMARO: I don’t get into that. We’re going to be criticized and praised for every deal. There are always two sides of the coin. We can’t operate based on criticism. We have to operate on what we think is right for the organization.

Q: One last time. Howard for Albert Pujols. Was it ever discussed internally?

AMARO: Those are not things we would discuss publicly even if we did discuss them internally. I don’t remember having any discussions about it. Could it have happened? I don’t know. When people talk about things internally, there are a whole slew of things that get talked about. It would be silly for me to even comment on it.

Q: That sounds like a non-denial.

AMARO: I honestly don’t remember ever speaking about having any type of discussions. We did know they would be free agents at the same time. We’re not dopes. But I don’t remember having any discussions about any trades between the two players.

Q: Ruben, there has been a lot of talk about the difficulty of the Phillies keeping Jayson Werth. You seem to feel that there is still a chance. Why is that?

AMARO: As I’ve said all along, we would love to keep Jayson Werth. This doesn’t necessarily preclude us from signing Jayson Werth. There are creative ways to get all the pieces of the puzzle if you can. If we can get all of the pieces of the puzzle, including Jayson Werth long-term, that would be great. If we can’t, we’ll move on and move forward.

Q: How important is his right-handed presence, especially the way you’re configured with Howard, Chase Utley and Raul Ibanez in the middle of your order?

AMARO: It’s important, no question about it. We’d like to have as much balance as we can. We’ve got some flexibility with some of the switch-hitters that we have. But any time you have balance, it helps.

Q: What about Jimmy Rollins? He’s a free agent after 2011. How important is he?

AMARO: He’s a pretty special shortstop, maybe the best shortstop in the National League, arguably one of the best shortstops in baseball. He’s another guy we’d love to keep long-term. At the appropriate time, we’ll have discussions with him, I’m sure, and see if we can extend him past 2011.

Q: You’ve got more than $130 million committed in 2011. You told me in spring training, “The payroll can’t continue to go north.” Yet, you’ve signed Howard and still want to keep Werth and Rollins. Where is the limit? How will you balance it all out?

AMARO: We will try to figure it out.