An exercise in futility: possible Derek Jeter destinations

In the 2009 documentary “Mr. Warmth: The Don Rickles Project,” the 80-something-year-old comedian recalls a story about threatening to run away from home when he was just eight years old. The reason behind his decision was typical: one day his mother was yelling at him and Rickles got “fed up” and declared he was leaving. Just like that.

His mother, being a realist and knowing the young boy’s petulance wouldn’t last, acts disinterested and even helps him pack his suitcase. “Tell my father I left,” says the young Rickles as walks out the door. A few minutes later, the young boy is waiting at the bus stop wondering if his mother will ever give in and beg for him to come home. Just then he hears his mother open the window and yell, “You forgot your sweater!”


This story made me think of the current Derek Jeter/New York Yankees negotiation. Here we have a beloved New York sports hero, a multiple World Series winning Yankee, firmly implanted among the greatest to ever wear the pinstripes and poised to reach the 3,000-hit milestone next season.

It’s almost unfathomable to imagine the Yankees letting Jeter walk away and equally unbelievable to see Jeter willingly achieve his 3,000th hit and close out his career in another uniform.

According to reports, the Yankees are “prepared” to offer Jeter a three-year contract worth $45 million. In today’s baseball economy, this contract has been estimated to be well above market value and the Yankees know this. Among those in Jeter’s camp this offer is expected to be considered unacceptable. The Yankees captain believes he can contribute well into his 40s and is looking for a minimum of four years but believes a five-year contract is reasonable.

Shuffling through a majority of the news and rumors, we get a lot of unnamed sources, including one stating that someone inside the Yankees’ front office is determined to stand firm at three years.

Via Wallace Mathews, ESPN New York:

Tell him the deal is three years at $15 million a year, take it or leave it,” goes the hard-line approach. “Wait him out and he’ll wind up taking it. Where’s he gonna go, Cincinnati?”

With that quote, let’s begin this charade by taking a look at Cincinnati:

After their successful 2010 season ended, conflicting reports have come. Some say the Reds are willing to enter 2011 with Paul Janish as their everyday shortstop while other reports have them in the market for one. Reds general manager Walt Jocketty has made it known that his team will be looking for an everyday leadoff hitter this offseason. Jeter would fit the bill next season, but is it worth five years at $75 million, especially with all the raises due to Joey Votto, Jay Bruce (Super 2 status) and Johnny Cueto?

If the Reds decide to upgrade at short and/or grab a leadoff hitter, I predict they flip one of their starters (as of now they have six and if you count Aroldis Chapman, that makes seven) as a trade piece, or they go with Janish or try to sign Orlando Cabrera or J.J. Hardy (assuming the Twins decide to non-tender him) on the cheap.

Speaking of the Twins, if they do elect to non-tender Hardy, that leaves shortstop open for Alexi Casilla and Trevor Plouffe to battle it out, since Orlando Hudson is expected to leave via free agency. I’m sure the Twins will save the money and plug in both players into the vacant middle infield.

The San Francisco Giants have been rumored to be interested in how the Jeter-Yankees negotiations play out. If the team elects to not bring back either Edgar Renteria or Juan Uribe, then Brandon Crawford, according to depth charts, becomes the de facto shortstop. Jeter would be tempting, but with the money invested in anchors like Barry Zito and Aaron Rowand, it would be lunacy to go that route again and pay five expensive years for a declining player.

Recently, a sportswriter in Baltimore has been pounding the drum for the Orioles to pursue Jeter. If all goes well in Oriole prospect land, Manny Machado will be at least two to three years away from being an everyday shortstop, but would it make sense for the O’s to sign an expensive veteran for five years?

And would Jeter honestly want to spend his final years scratching to get out of the cellar in the AL East?

A Hardball Times Update
Goodbye for now.

Just for fun, let’s imagine the Red Sox jumping into this fight.

Peter Abraham of the Boston Globe finds it hard to resist and speculates, with the preface that this has almost no chance of becoming a reality, on what it would take for Jeter to jump ship. It’s a fun read but Abraham’s proposal of two years at $20 million is way below the Yankees’ proposed offer. Rumors have circulated that a few teams have inquired about the availability of Marco Scutaro, but if that happens Jed Lowrie becomes their full-time shortstop. So that’s settled, and besides, Jeter is way too self-aware of his legacy as a Yankee to damage it like this.

What about the Tampa Bay Rays, you ask?

Jeter does have a home and established fan base in that section of Florida, but signing a player on the decline like Jeter to the years and money he would expect goes completely against their offseason plan to become younger and cheaper. Again, not happening.

The Dodgers do have the big-market presence and the Yankees connections to make this a legitimate destination. And general manager Ned Colletti does have the reputation for loving the veterans, but then there’s their ownership situation and incumbent shortstop Rafael Furcal. Also, Dee Gordon is still considered too valuable a prospect to block past 2011. Gordon still has defensive issues, but many scouts see him sticking at short. The Dodgers have enough headaches. Pass.

The Mets are in New York, which by default makes them a possible landing spot for Jeter. Reports do have them actively shopping Jose Reyes, but with Wilmer Flores in the pipeline and a new regime looking to clean up payroll, this has no chance of happening.

Cardinals general manager John Mozeliak said his team will be actively searching for an upgrade at shortstop this offseason. The free agent market at short does look a bit barren, but with a team still wondering how to pay franchise player Albert Pujols, do you really believe the Cardinals will make Jeter their highest-paid player next season and possibly beyond? No way.

Further up north we have Chicago, where the Cubs have Starlin Castro, who profiles as a future second baseman, but it wouldn’t be Jeter moving him over since Hak-Ju Lee shouldn’t be too far behind.

Over on the South Side, the White Sox has the front office with the capacity to surprise, but acquiring Jeter would only work if he agreed to be a light-hitting DH, which I’m sure is a deal-breaker. If (and this is a big if) the White Sox brought in Jeter, they would have to trade away either Alexei Ramirez or Gordon Beckham. They could get some value out of Ramirez but they would be selling low on Beckham. I think it would be a mistake and not make any financial sense to replace an above-average shortstop who will be 29 years old at the start of next season, is locked in to make a little over a million dollars next season, and doesn’t qualify for free agency until after 2013.

Those are just a few possible destinations I’ve seen tossed around and, obviously, nothing seems to fit. If I had to choose which of the above destinations would be willing to make any kind of serious offer to Jeter, I would be torn between the Reds and the White Sox, but signing Jeter away from the Yankees would take at least five years at $75 million, and maybe more if a team truly wanted to blow the Yankees away.

I can’t see a team in baseball making that kind of commitment to a player clearly in decline. It’s obvious that both sides in New York value each other since Jeter’s legacy was made possible by playing for the right team at the right time while the Yankees have benefited from Jeter’s presence since his rookie season in 1996.

This is probably just a huge case of each side trying to save face and not spill this over into some nasty public feud. When it’s all said and done, sometime after the Thanksgiving holiday, I predict Jeter goes back home, gets his sweater and stays there. Both sides will come to a compromise as they settle on a three-year deal with a mutual fourth year option.

The Yankees will have overpaid. Jeter won’t have gotten exactly what he wants, but he also will have kept his dignity intact, by not offering himself up at an “old guy discount.” And the deal will still be miles away from anything another team could hope to offer.

All will be good in the Yankee/Jeter home.

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Jim C
13 years ago

I do not understand why Jeter wants more than three years. He has won several Series, already has more money than he could ever spend, will be the only career Yankee with 3000 hits, will instantly have his number retired and a huge presence in Monument Park. If he plays 5 more years, his legacy will be tarnished just as has every player who hung on too long. Remember how bad Willie Mays looked at the end? Steve Carlton? As smart as Jeter is, you would think he would not end up like so many, with completely deteriorated skills and having the jersey ripped off his back and being kicked out the door.

13 years ago

Nothing much surprises me anymore, but as a White Sox fan I can think of about 5 holes bigger than middle infield and at least a dozen guys I’d rather throw 5/$75M at this winter.

Jim W.
13 years ago

As much as it would make little sense from a team-building and financial standpoint, part of me still would like to see the BoSox pony up for Jeter as a reverse Boggs/Clemens/Damon sort of move.

13 years ago

I’m rooting for Jeter to get a six year 120m contract.  He should get the same contract ARod has:
11:$31M, 12:$29M, 13:$28M, 14:$25M, 15:$21M, 16:$20M, 17:$20M

Those two contracts could cripple even the Yankees for a decade.

John P.McDermott
13 years ago

Jeter as Boston SS @ 20 Million for 2 yrs with a Team option for $10 million for the 3rd , makes sense , but it would have to be right now.
” It aint gonna happen”
read the NY papers , Jeter and Yankees agree this week .