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St. Louis Cardinals trades: Jason Heyward and negotiating windows

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How much does the possibility that a player might sign to play with a team beyond his current contract play into a team's decision to trade for him?

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When the St. Louis Cardinals acquired Jason Heyward from the Atlanta Braves this offseason, they acquired a "five-plus" player. The five-plus label doesn't refer to Heyward's tools, but his MLB service time—Heyward has over five years of it. Under the terms of the collective bargaining agreement between MLB and the Players Association, players can become free agents in the offseason after accruing six years of MLB service time. Because of this, Heyward will be a free agent after the 2015 season.

Heyward's contract situation has been the subject of analysis. At the St. Louis Post-Dispatch, columnist Bernie Miklasz wrote that the Cardinals can afford to sign him to play future seasons in St. Louis. Here, Craig opined that the Cardinals should rush to sign Heyward to an extension if he is willing to accept a team-friendly salary in order to avoid him leaving for a bigger payday via free agency after a good season at the plate.

The idea that Heyward may sign a Cardinals-friendly contract to play in St. Louis seems to have gained some traction among fans. In the comments section to Joe's piece looking at the Cards' free-agent signings and asking folks to grade general manager John Mozeliak, some gave alternative grades based on whether Heyward signed an extension before the end of 2015 or as a free agent after the season. Memories of the Jocketty era win-now trades and subsequent extensions are still strong. You'll recall that the Cards acquired Jim Edmonds in March 2000 and signed the outfielder to an extension in May 2000. St. Louis moved just as quickly with third baseman Scott Rolen, who the Cardinals acquired at the 2002 trade deadline and signed to an extension in September that same season. Matt Holliday's free-agent contract also came up.

At Baseball Prospectus, Sahadev Sharma wrote an article on the value of five-plus players which you should read in its entirety. The focus of the piece is primarily five-plus pitchers, but it offers a window into the thinking behind acquiring such players, with quotes from Theo Epstein, Jed Hoyer, and Rick Hahn. The Cubs traded Jeff Samardzija, a five-plus pitcher, to Oakland last season and Hahn recently acquired Samardzija from the A's. From Sharma's article:

Hahn was very clear as to what the White Sox were acquiring in this deal: one year of Samardzija and exclusivity in negotiation rights; so, basically, a little less than a year of time to convince Samardzija that re-signing with the White Sox was in his best interests.

"It’s difficult to quantify, but does it put you in a better position (to re-sign the player)? I believe it does," Hahn said last week at the Winter Meetings. "Because there’s a level of familiarity, there’s hopefully a level of trust. There’s a level of understanding of the direction of the club, whereas the player needs to get familiar with others once they enter the free agent market. It certainly isn’t controlling, it certainly doesn’t put you leagues ahead of everybody else. But we think there’s a benefit to it, there’s certainly a benefit to it. If you’re not going to be competitive on the dollars, then it’s probably not going to matter in the end."

And that’s likely the most important part of what Hahn said: Any deal that Samardzija might sign with the White Sox would likely be at or very near what he’d command on the open market. It’s unlikely that the opportunity to re-sign Samardzija weighed heavily when the White Sox considered what they’d be willing to part with for his one year of services. As Cubs president of baseball operations Theo Epstein noted, most people outside of baseball tend to overvalue that exclusive negotiation period.

"Probably not as much as you might think," Epstein said when asked how much teams value the opportunity to possibly extend a player when deciding how much to give up for their services. "You get to know the player and he gets to know the situation, but sometimes when players get within a year of free agency, it’s hard to get them off that opportunity."

And while Hahn did say it was something they looked at, the White Sox didn’t pay much extra for that right. Hahn did point out that getting Ynoa in return made the deal more palatable.

"It was a balancing act. There’s no exact science to calculating the value of what we truly were receiving versus what we were giving up," Hahn said. "But I think in the end, once we got to the four-for-two structure and received a prospect back in the deal, we all felt more comfortable with it on our side."

This isn't insight into Mozeliak's thinking, though there are parallels between the second Samardzija deal and Heyward trade. The Cardinals gave up eleven seasons of cost-controlled pitching in the form of Shelby Miller and Tyrell Jenkins in exchange for one expensive season of Heyward and two cost-controlled years of reliever Jordan Walden. To me, it seems clear the Cardinals acquired Heyward to play right field in 2015 and, while they are certainly open to having him wear the birds on the bat beyond that, I didn't think the window to negotiate an extension played a major role in the acquisition. With an aging core of Holliday, Jhonny Peralta, Yadier Molina, and Adam Wainwright, the Cards added Heyward first and foremost to help them win in 2015.

Extensions like those signed by Edmonds and Rolen are a rare breed nowadays, if not extinct. Players are seemingly less willing to ink a team-friendly contract while so close to becoming a free agent, able to explore each of the 30 MLB clubs as a potential employer. There's a reason that Shin-Soo Choo isn't on the Cincinnati Reds today after Jocketty acquired the five-plus outfielder for the 2013 season.

Holliday's free agency is also instructive. The Cardinals' negotiations with were so rocky they almost ended with St. Louis walking away, according to an anecdote Joe Strauss shared in a St. Louis Post-Dispatch column profiling Mozeliak two offseasons ago.

Mozeliak refers to DeWitt as his mentor. However, it was Mozeliak who talked DeWitt into resuming negotiations for left fielder Matt Holliday when it appeared DeWitt would walk away from edgy talks with agent Scott Boras.

The Cardinals wound up agreeing to a seven-year, $120 million contract with the free agent. While Holliday has provided the Cardinals surplus value so far during the contract (according to Fangraphs' valuation, his play has been worth $109.7 million while earning $85 million over its first five seasons), the deal was right in line with the market for free-agent outfielders, which had sagged a bit due to the financial collapse of the year prior and some of the usual high-spenders sitting out the bidding because of full outfields.

It seems likely that the Cardinals acquired Heyward for the contributions he will make during the 2015 season. Whether he is a Cardinal beyond that was likely a minor consideration when deciding whether to pull the trigger on the trade that brought him to St. Louis. We as fans should probably keep that in mind, even when (if?) the Cardinals start negotiations about Heyward wearing the birds on the bat for a longer time period than that. The trade won't be made by Heyward starting in right field on opening day 2016 and beyond.

Correction: The original version of this post incorrectly stated the date of the Edmonds trade. It has been corrected.