The Other Shoe: Extend Others Beyond Carp?

Following on the heels of Monday's extension of Chris Carpenter's contract, what might Walt Jocketty do next in terms of similar deals with players close to home?

Prior to Monday's announcement of Chris Carpenter agreeing to five more years with the Cardinals, most watchers of the club had been totally focused on free agents and trades. They still are. But, we have long been thinking about the players that remain, too.

In fact, I want to share something with you, our subscribers. Several emailed me, wondering how I posted such a detailed analysis of the implications of Carpenter's signing so quickly after the news of his extension was public late Monday afternoon.

In all honesty, I had already written 95% of that article last Saturday night, along with 95% of what follows here. I was holding the story because we already had so much new, topical content on the site and I didn't think there would be an announcement on Carp so soon. My bad. Only my faithful assistant Woody, who proof-read the story, can vouch for me, though.

I also want to quietly remind you that we forecasted the Kip Wells and Adam Kennedy signings. While the rumor business never allows one to become infallible, it is nice to have them come through.

Anyway, as I said, what follows is the back-end of the original Carpenter extension story, looking at three players who may or may not be prime candidates for contract extensions, too.

An Eck-stension also coming?

A well-placed source told me an interesting piece of information about second baseman Adam Kennedy's recent negotiations with the Cardinals.

As many know, Kennedy was joined by shortstop David Eckstein to serve as the keystone combination for the then-Anaheim Angels from 2001 through 2004, including their 2002 World Championship season together.

During the course of Kennedy's recent free agent discussions with the Cardinals, the two sides discussed both money and duration of contract, of course.

Most observers believe the Cardinals made out extremely well in both areas, as Kennedy agreed to a three-year, $10 million deal that interestingly looks quite similar to the one his past and future shortstop partner inked two years ago.

Turns out the Cardinals were asked to provide a unique assurance that apparently had weight in Kennedy's decision to sign or not.

Specifically, I was told that Kennedy asked point-blank if Eckstein would be remaining with the Cardinals for the duration of the second baseman's new contract. Knowing what the right answer was, the Cards told him exactly what he wanted to hear, "Yes".

Whether or not the Cardinals informed Eckstein of this, I bet Kennedy sure did!

As a side point, this illustrates a whole undercurrent in this free agent business that most do not understand and appreciate. That is the network among players.

Think about it. They are people, just like us, with long-time friends, many that were established in their workplace. They freely talk among themselves, sharing information and gossiping like those on our message board. They lobby each other, share contract details and even joke and boast. Sometimes, they get rumors wrong and even change their minds!

I am not saying that Eckstein was the only factor that played into Kennedy's decision. That would be foolish. In fact, I don't how important it was. But, I do know that it was discussed and the answer was noted.

Back to the question at hand. For reference, 2007 is the final season of Eckstein's initial contract as a Cardinal, signed after he was non-tendered by the Angels in December, 2004 - a deal that brought him $10.25 million over the 2005-2007 seasons.

Though I was critical of the third year given Eckstein at the time, again Jocketty proved why he is one of the top GMs in the game. The diminutive shortshop will be making $4.5 million this season, an amount that sounded too high in 2004, but is reasonable in today's inflated market.

So, if this Kennedy story is as I presented, it would seem that Jocketty plans to get to work on a new deal for his World Series Most Valuable Player before too long in order to keep the new middle infield combination together for at least two more years after 2007.

On a two or three-year extension, Eckstein would surely to be able to command an amount exceeding that of the only "big" shortstop signing so far this off-season. I am referring to Alex Gonzalez, who is not the player Eckstein is, yet fetched $14 million over three years from the Cincinnati Reds.

(Update: Julio Lugo, a superior shortstop to Eckstein, agreed to terms with the Boston Red Sox on a four-year, $36 million contract.)

Is three years, $18 million for Eckstein out of the question in this ever-expanding market? To how much would it grow next off-season if not addressed now?

More Molina moola?

Of the Cardinals players with fewer than six years of experience, in other words, those who are not yet free-agent eligible, catcher Yadier Molina is the one who stands out as being best positioned to make considerably more money in the near future. In terms of experience, his peer group on the club includes supporting players like Aaron Miles, So Taguchi, Randy Flores and Josh Hancock.

As I noted on November 24 in "Love Me (Non) Tender", Molina fell seven days short of qualifying for arbitration for the first time as a "Super Two" player this year. So, the catcher's three arbitration-eligible years will start next off-season instead.

Despite a poor regular season with the bat, Molina was arguably the Cardinals' best hitter in October. His value defensively is unquestioned. So, it might seem a good idea for Jocketty to consider a multi-year deal with Molina sometime in the next twelve months that would tie up some or all of the backstop's arbitration-eligible years.

If Walt doesn't want to do a deal now and as a practice doesn't work deals during the season, he would have to wait until next winter to consider Molina's case. With a young player on the upturn however, the risk is that Molina has a breakout offensive season in 2007 and his price will go up accordingly.

Even this year, if left to arbitration, Molina might have been able to secure a deal in the $1.5 million range. Next year, it likely will be more.

Still, with more pressing immediate matters, the Cardinals could easily take the path of least resistance and just give Yadi a nice raise for 2007, perhaps doubling his $400,000 2006 pay and wait until later to take action on the long-term.

Not Izzy time

Another core member of the Cardinals, closer Jason Isringhausen, could be in the final year of his current contract. Yet, given his age (34) and injury history, including four surgeries, the most recent done on his hip this fall, it would be most prudent to see what kind of 2007 campaign Izzy could post before making any decision on his future.

Since becoming a Cardinal in 2002, Izzy has been paid a salary comparable to the top closers in the game, but his next contract would be covering years that could be expected to represent the downside of his career.

Isringhausen will make $8.75 million in 2007, same as 2006. The Cardinals have an $8 million team option for 2008, with a $1.25 million buyout. So, they could keep him for another season or cut their ties.

Deciding Izzy's future on the club beyond 2007 could either turn out to be difficult for the Cardinals, especially with lower-cost alternatives such as Adam Wainwright under team control, or the veteran closer's health could make the answer obvious to all.

For 2007, while reports from Izzy on the progress of his most recent rehab are promising, it is prudent to keep expectations in check until proven otherwise on the field of play. In other words, Walt Jocketty would be wise to have another starting pitching option ready in case Wainwright is needed to close.

Where's all the money gonna' come from?

By some estimates I have read, the Cardinals may have come into this week with $15 million to as much as $25 million remaining in their war chest to spend to complete their 2007 roster.

While much of the money speculated about above, for Eckstein and Molina as well as Chris Carpenter, would probably be paid in the out years, not necessarily in 2007, one might envision a scenario where some considerable-sized signing bonuses were paid sooner.

That would ease the dramatic increase in total payroll that is going to occur each year as the built-in raises for many of the Cardinals front-liners kick in, including players like Albert Pujols, Scott Rolen and of course, Carpenter.

In that "pre-pay" scenario, some of that 2007 budget "excess" could disappear in a few heartbeats if Jocketty looks to extend the amount of time he can keep some of these key players beyond 2007.

These three, Carpenter, Eckstein and Molina, look to be as sure of a long-term bet to excel as just about any player on the club. So, the only question is whether the Cardinals pay a lot now or risk paying even more later.

Monday's announcement of Carpenter's five-year extension was a first step in answering that. Will Eckstein and Molina soon follow?

Brian Walton can be reached via email at

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