A former general manager offers three deadline rules to remember

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Five years ago this week, the Orioles were deep into talks with both the Astros and Angels as they attempted to unload Miguel Tejada in a blockbuster trade. If they consummated the Angels deal, they would get Ervin Santana, Erick Aybar and Jose Arredondo in exchange for Tejada, according to Jim Duquette, who was then the vice president of baseball operations for Baltimore; if they did the Astros deal, they were going to get Roy Oswalt, Morgan Ensberg and Adam Everett.

Duquette says he still shakes his head at how hard he and GM Mike Flanagan worked on moving Tejada that July. The executives had been on the phone for weeks, Duquette says, and were exploring so many different options that "we literally had charts, like flow charts, with arrows that were pointing to different teams so that we could keep track of where each player was going in whatever variation of the deal we were talking about."

Finally, they settled on the Houston version with the Angels alternative as a solid back-up. They gathered up their materials and headed over to "the law offices," as Duquette describes it, where they planned to present the situation to Peter Angelos, the Baltimore attorney who has owned the Orioles since 1993.

"We were excited," Duquette says. "Until ..."

Until Angelos nixed the entire thing.

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Even now, Duquette still laughs at the memory. All the weeks of work, all the negotiating and cajoling, had turned out worthless. Angelos, when it came time to give his final blessing, did not want to trade Tejada (remember, this was before the Mitchell Report was released with Tejada's name included) and the entire episode left a lasting impression on Duquette, who now works as a host on Sirius XM Radio. In an interview this week with SI.com, Duquette, who went on to be the general manager of the Mets, laid out his three basic trading season rules for GMs -- starting with the one that was hammered home that afternoon in Angelos's office ...

Rule No. 1: Whenever possible, get prior approval

It wasn't just the disappointment of the trade with the Astros (or Angels) falling through; Duquette and Flanagan were also peeved about Angelos quashing their deal because they had already been in talks about a second trade they would do if they were able to land the crop of Houston players.

"We were pretty far along in talks about maybe flipping Oswalt to the Mets for (Lastings) Milledge and (Aaron) Heilman, or even to the Rangers for (John) Danks and a kid, Thomas Diamond," Duquette recalled. "Obviously all of that went in the trash, too."

Truth is, everyone has ownership issues. Players are ruled off limits and trades are scuttled all the time because of input from ownership, and GMs will always serve at the pleasure of the president (or the CEO or the general partner). When Duquette was the Mets' GM, he made a much-scrutinized deal that sent Scott Kazmir, then a 20-year-old top pitching prospect, to Tampa Bay for veteran starter Victor Zambrano. Duquette did so because the feeling in the organization was that the Mets needed to acquire inexpensive, controllable and experienced starting pitching that could help them erase either a 6-game hole in the NL East or a 7 ½ game deficit in the wild card race. "That was what our focus was at the time," Duquette says. "We did what we had to do."

So, yes, there will always be the specter of ownership hanging over every discussion, but particularly as the trade deadline approaches and time is of the essence, it's critical for GMs to be able to negotiate with each other knowing that an agreement is possible.

"You don't want to be the guy running back and forth between conversations every minute," Duquette says. "That just makes things more difficult. You want to feel like you're negotiating in good faith with the guy on the other end of the line."

Along those lines ...

Rule No. 2: Know the code

Yankees GM Brian Cashman has always said publicly that he harbors no ill-will over what happened last year, when the Yankees were on the verge of trading for Mariners ace Cliff Lee only to see the deal fall apart at the last minute and Lee be dealt to the Rangers instead. In interviews, Cashman has been steadfast in saying that a deal isn't done until everything is signed, refusing to lash out over how the deal (or non-deal, really) went down.

Duquette, however, says that it isn't really that black and white in the trade game. One of the main sticking points in the Mariners-Yankees talks was whether Cashman would relinquish top prospect Jesus Montero, and once he agreed to do so, the bulk of the negotiations was complete. According to Duquette, that is baseball's version of a handshake agreement; barring a major disaster, the deal should go through.

Instead, Mariners GM Jack Zduriencik came back to Cashman and said he had found an issue with an injury to David Adams, a Yankees minor league infielder who was a significantly smaller piece of the deal; instead of quickly finding a replacement player agreeable to both sides (because, after all, Montero was the major piece the Yankees were giving up), Zduriencik asked for a much higher-quality replacement -- believed to be either pitcher Ivan Nova or infielder Eduardo Nuñez. When Cashman (understandably) balked, Zduriencik turned around and did the deal with Texas, which was willing to give up top prospect Justin Smoak.

"With something like that, if you've got a problem with a player you've got to work out a solution," Duquette says. "You can't blow a deal up over that. It's not right."

That isn't to say that last-minute posturing isn't allowed (or even encouraged). Duquette likens it to buying a car, where after you agree on a price you still try to get the salesman to throw in free satellite radio or an upgraded speaker system.

As an example, Duquette pointed to 2004, when he was the GM of the Mets, and made a deal with the Orioles in which he essentially swapped Ty Wigginton for Kris Benson. The deal had been percolating for two months and, in the beginning, the Orioles kept asking for David Wright. "David Wright, David Wright, David Wright -- that's all they kept asking for," Duquette says. "And I said no as politely as I could but kept the conversation going."

By the time the deadline approached, the Orioles' demands had dropped and an agreement was reached with Duquette sending Wigginton, Matt Peterson and Jose Bautista (not that one) to Baltimore for Benson.

"But then at the end, I said, 'Look, we need something else -- give me Jeff Keppinger, too,'" Duquette says.

Would Duquette have walked away from the deal if the Orioles said no? Probably not. Because that wouldn't have been right. But he had good scouting reports on Keppinger so he asked and, after a brief back and forth, Baltimore threw the equivalent of free floormats into the deal, too.

Of course, simply by bringing up Keppinger's name -- even at the last minute -- Duquette had increased that player's value, which is an important aspect of ...

Rule No. 3: Be aware that every single conversation -- however brief -- has consequences

Ubaldo Jimenez has been a hot name on this year's trade market but amidst the rumors is an undercurrent of suspicion from executives around the league. Jimenez has a very team-friendly contract -- he's under Colorado's control through 2014 for less than $18 million total -- so the lingering question is: Why would the Rockies even consider trading him? What do they know about Jimenez that everyone else doesn't?

Those concerns are just the latest example of Rule No. 3, which, roughly translated, says that everything you do (and don't do) affects everything else you do (and don't do).

That's why negotiations can at times be interminable shell games. One team will make an offer and the second team will reject it but refuse to counter. Why? "Because if they counter, the first team will assume that whichever players are in the counter are no good," Duquette says. "If they were any good, why would the second GM be OK with giving them up?"

Memories are long in baseball, too. In 2000, the Mets nearly traded for the Reds' All-Star shortstop Barry Larkin, hoping to use him as a half-season rental filling in for Rey Ordoñez, who was injured. The deal ultimately fell apart because the Mets didn't want to give Larkin a contract extension, but it was well-known that they were willing to give up Alex Escobar, one of their top prospects, in exchange for Larkin.

A full year later, the Mets were in talks with the Indians about a trade involving Roberto Alomar, and Escobar was at the heart of those discussions, too. The problem was, according to Duquette, that Cleveland GM Mark Shapiro knew the Mets had been willing to give up Escobar for Larkin a year earlier and thought that meant something was wrong with Escobar.

"They were reluctant because they were like, 'Why would you trade Escobar for a rental?'" Duquette says.

In the end, the Indians did the deal but after it was completed, Shapiro called Duquette, who was an assistant GM at the time. "He was like, 'All right, just tell me: What's wrong with Escobar?'" Duquette says. Duquette laughed. "It was just a reminder that at this time of year, everything -- everything -- matters."