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Why The Red Sox Should Pursue Derek Jeter

Derek Jeter

This past week, the New York Post published a photo of Derek Jeter in a Red Sox uniform after Yankees GM Brian Cashman told Jeter to see if he can find a better deal than the three-year, $45 million one he turned down. There’s no way Jeter would join the Red Sox, right? That’s like Roger Clemens or Wade Boggs heading to the Bronx…oh wait. That actually happened. Now that the Red Sox are willing to spend and willing to win every year under the relatively new ownership, you have to begin to wonder: will Derek Jeter be wearing a Red Sox uniform in 2011?

According to New York Times reporter Michael S. Schmidt, Jeter and agent Casey Close are seeking between $23 and $24 million per year for four or five years, which would take the shortstop past the age of 40 in Yankees uniform. In case you didn’t do well in math, there’s a gigantic gap between Jeter’s request and New York’s offer. So, what’s going to give?

The Likely Scenario

First, before I tell you why the Red Sox should pursue and not necessarily sign Jeter, let me tell you something you already know. Jeter will remain in New York for the rest of his career, and it will probably be for about $18-19 million per year over four years (a compromise between Jeter and Cashman’s proposals). While that’s a lot of money to you or me or even a backup major leaguer like Gabe Kapler, Jeter is coming off a 10-year, $189 million deal, and he would like a pay raise for all that he has done over the years.

Jeter may be returning to New York eventually, but it will be a painful process. Why are the Yankees “low-balling” Jeter?

Jeter’s Decline

Well, let’s start by saying the Yankees are actually offering Jeter more than he’s worth. Looking at the Yankees shortstop without pinstripe-colored glasses, and you see a 36-year-old shortstop with diminishing range and weakening bat speed. The evidence?


Despite winning an unbelievable fifth Gold Glove Award a few weeks ago, Jeter was undeserving, and that’s a nice way to put it. He led AL shortstops with a .989 fielding percentage and just six errors in 151 games, and if you leave it at that, then you agree that Rafael Palmeiro deserved his 1999 Gold Glove Award. In that season, Palmeiro played just 28 games at first base and most of the rest at DH, but hey, he only had one error!

You see, there are defensive metrics to prove Jeter should not have won the 2010 Gold Glove at SS. His range, as you may have noticed, has diminished even more as the years have gone on. Despite his trademark running-backwards-jump throw to first base that dazzles simple fans and managers alike, Jeter is an average, at best, major league defensive player.

Using the Ultimate Zone Rating (UZR) is often viewed as a fair judgement of a player’s defensive ability. UZR measures “the number of runs above or below average a fielder is in both range runs, outfield arm runs, double play runs and error runs combined.”

“I hear about this UZR, Ultimate Zone Rating. And I saw Robinson Cano has a negative Ultimate Zone Rating. That is absolutely crazy,” Teixeira said. “Robinson Cano is by far .. . the best second baseman I’ve ever seen and he’s a negative defender by that Ultimate Zone Rating. So I don’t put any stock into those things.”

Taking Tex’s biased look out of the picture, let’s place Jeter in this metric. It turns out he was the sixth worst shortstop in all of baseball (minimum 1000 innings), posting a -4.7 rating. A 0.0 rating indicates that a player is average when compared to other shortstops’ range during that same season. In simpler terms, Jeter likely cost his team more runs than he saved.

OK, so he’s no Ozzie Smith. What about his bat?


Jeter has been one of the most consistent players in all of baseball over the last 15 seasons, but we have reach a point where we can finally question his ability to keep it up. For the first time in his major league career, Jeter hit under .290 over the course of a full season in 2010. In fact, he hit just .270 with a .340 on-base percentage and a weak .390 slugging percentage, the lowest in his career.

Usually, players bring their games to new levels in their contract years, but Jeter had the worst year of his career, which indicates the decline may have already taken shape. Bill James has released his early projections of Jeter’s 2011 season (assuming it’s with NY), and he predicts the shortstop will hit .295 with a .365 OBP and .410 SLG.

They are pretty good projections…but is an aging shortstop with poor range and slowing bat speed really worth $19 million? How about $15 million?

The Case for Jeter

Based on numbers alone, Jeter is probably worth about $10 million per year for a maximum of three years (and I think I’m being generous on the length of the potential deal). But, the Yankees almost have to consider goodwill and his past performance when reaching their final agreement with the future Hall-of-Famer. (It’s worth noting that in the past, that hasn’t stopped them: Yogi Berra, Reggie Jackson, and even the Babe finished their careers with other teams.)

Without George Steinbrenner running the show in New York, it would appear the Yanks are going to play hardball until someone dares them otherwise. If George were still alive, he probably would have ordered Cashman to finish the negotiations quickly and behind closed doors, but this is a different administration in New York, one that is willing to watch their wallets a bit despite their gigantic budget. Jeter will play baseball next year, and Cashman and co. are gambling that no one will offer the shortstop anywhere near the amount of money he’s looking for.

That’s where the Red Sox step in. Aside from the Mets, Angels, and maybe a handful of other times, they are one of the only ones that can afford Jeter’s services. What would it hurt to talk to Jeter? If anything, it would force the Yankees to shell out more money over more years, until they are stuck with a 41-year-old Jeter making $19-20 million as a washed up, backup infielder.

Jeter will likely reach 3,000 hits next year, and if he plays six more years, he has a real outside shot at 4,000. If Jeter sets that mark or any other record in a Red Sox uniform, George will roll over in his grave and the Yankees faithful will collectively vomit. Imagine Ted Williams hitting a home run in his final at bat…while wearing a Yankees uniform. Hell, imagine David Ortiz or Dustin Pedroia finishing out their careers in pinstripes. Scary thought, huh?

Final Thoughts

The potential of Jeter joining the Red Sox could sway the Yankees to spend a bit more on their legendary shortstop. It should, at least. In the most likely scenario, as stated earlier, Jeter will sign a four-year deal at around $19 million. In that situation, Jeter can’t complain he’s taking a pay cut (he’s coming off a contract in which he averaged an $18.9 million salary), and he can walk away from the situation with his head (sort of) held high.

Red Sox involvement in the negotiations could push the Yankees to add a year and a few million dollars per year on their offer. In that case, the Red Sox would cost the Yankees at least an extra $25 million (by my estimation). What’s the harm in that?

Well, if the Red Sox “make an offer” to make the Yankees spend more and Jeter actually signs on the dotted line with Boston, that’s probably the worst-case scenario. Tread softly, Theo. Tread softly.

About KC Downey - @kc_downey

KC is the "head coach" of the Sports of Boston, LLC blog network. Follow him on Twitter: @kc_downey

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6 comments for “Why The Red Sox Should Pursue Derek Jeter”

  1. Wow. Three article on this site and all are crap. Do you REALLY believe Theo will even pick up the phone? Put it this way, if you’re going to spend $17-18 million a year on a player, would you want Derek Jeter or Carl Crawford on the Red Sux? Not even Boston fans are dumb enough to say Jeter would help more than Crawford would. Why would Theo “make an offer” to a player he doesn’t want to sign? That’s complete idiocy. If jeter says “Yes,” is Theo supposed to say “Ohhh, we were just kidding”?

    Plus, do you REALLY think Theo wants to start global thermonuclear war with the Yankees? If so, say goodbye to Cliff Lee, Carl Crawford and any other free-agent your team will even THINK about signing for the next decade. The Yankees would run their payroll up to $300 million just for the heck of it. Think about the future. Lincecum in three years? To the Yankees. Price in four years? To the Yankees. Theo would be begging players to come to Boston and being denied over and over, left to think “Maybe I shouldn’t have made that offer to Jeter just to rile up my idiot fans and dumber bloggers.” Rather than “tread softly,” don’t tread at all.

    Posted by NYCTim | November 27, 2010, 11:08 pm
  2. NYCTim: No, I don’t believe he’ll entertain the idea too seriously. But, GMs make calls on all types of players all the time, even if they are just kicking the tires a bit.

    You can talk contract with a player without having him sign. Hey, Teixeira did it with the Red Sox a few years ago. He came to the Sox, said “what can you offer” and went back to the Yankees to ask for a little more. It’s free agency, and it’s Jeter’s right as a free agent to test the market.


    And on your second point…yeah, why not? If they would be so royally pissed about the Sox kicking the tires on Jeter…then isn’t that my point? The Yankees can overspend all they want! Remember Carl Pavano? Jaret Wright? Jason Giambi?

    Posted by KC Downey | November 28, 2010, 12:43 am
  3. Tim, you sound like you’re trying your best not to understand our points. Just because an idea is brought up and/or entertained doesn’t mean it will happen. Plus, I would love to see the Yankees run up their payroll, overtax their fans with expensive tickets and several thousand dollar turkey sandwich lunches. They’ll implode themselves quickly if they do that. Let the Yankees pay one player an extra $xy million dollars per year per player just because the Red Sox kick the tires a little (a huge overreaction, if they do it). Let them have Lincecum, Sabathia, and Lee for all I care. Let them talk about eight-peating. That talk and practice worked out SO WELL for the Miami Heat.

    And for that matter, you seem to be reading a lot of our articles if you think we’re as useless as you say. Maybe we’re good at what we do, and you just don’t want to admit it because you’re so pro-New York.

    Posted by John | November 28, 2010, 10:49 am
  4. No one in their right minds would offer Jeter more then the Yankees will. Even 3 years and 45 million is ridiculous for all of baseball.

    Posted by Dan | November 28, 2010, 2:30 pm
  5. […] A case was made at Sports of Boston over the weekend for the Red Sox pursuing New York Yankees’ iconic shortstop Derek Jeter, given the free agent’s unsuccessful contract negotiations with his former team. The argument seems to have gained some sway amongst the Boston sports media, as Boston Globe columnist Dan Shaughnessy wrote in Tuesday’s edition that the Red Sox should offer him a contract, and a big one at that. His reason: “to bust pinstripe chops for all the ages.” But, as with most things Shaughnessy, the minutiae of his argument do not hold up under scrutiny. […]

    Posted by A Poor Argument at Best: Shaughnessy on Jeter | Goose's Gabs | November 30, 2010, 7:10 pm
  6. […] "title": "A Poor Argument at Best: Shaughnessy on Jeter" }); GA_googleFillSlot("200×200"); A case was made at Sports of Boston over the weekend for the Red Sox pursuing New York Yankees’ iconic […]

    Posted by A Poor Argument at Best: Shaughnessy on Jeter | Sports of Boston | November 30, 2010, 9:57 pm

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