Derek Jeter’s New Yankee Contract Should Be 10 years – $200 Million

Johnny Damon was discussing his divorce from the New York Yankees to any media outlet who wanted to listen. On the WFAN radio show in New York, Damon discussed his Yankee divorce with host Mike Francesca. I want to say that I did not hear the interview live, but listened to the podcast and read its excerpts in the New York newspapers.

It is not the first divorce in Damon’s professional, or even personal life. One of the reasons bandied about Damon wanting to play solely for more money is that he lost millions in the divorce from his first wife. Then he supposedly lost even more in the Florida-based Allen Stanford $8 billion investment scandal.

Damon might have been better off marrying Stanford and investing money with his first wife.

During the interview Damon said, “Hopefully this doesn’t happen with Derek next year. I say there’s no way Derek can go anywhere else.”

While Damon did acknowledge that Jeter’s situation is completely different, he hopes Jeter doesn’t encounter similar negotiating difficulties with the team when the franchise’s all-time hits leader becomes a free agent next winter.

“… I hope he’s not offered a 40-45% pay cut. But I know Derek’s going to go out and produce this year and I know they will treat him with respect.”

I guarantee, Johnny, that the Yankees will treat Jeter with respect, and that Jeter will treat the Yankees with respect, too.

Jeter is the home grown winning Yankee star of my 12 year old son’s generation, just like Thurman Munson was of my generation and Joe DiMaggio was of my father’s generation. Those three players were our childhood heroes of three generations of Joseph DelGrippo’s. (Wow, three generations of opinionated sports fans is just way too much.)

All three of those Yankee greats were private individuals who won back to back World Series titles. Munson was the consummate family man, ultimately dying because of his desires to see his family during the season.

Jeter was more similar to DiMaggio. Both single, classy, and New York City savants who owned the Big Apple – if they so wanted, but both usually stayed behind the scenes loving their privacy.

Jeter knows his Yankee history, knows his place in that history as the leader of the late 90’s dynasty and the latest in the short list of Yankee Captains. He respected the Iron Horse when he broke Lou Gehrig’s All-Time Yankee hit record, he respected the Yankee fans with his great impromptu speech after the last game at the previous Yankee Stadium.

And he will respect the great DiMaggio by leaving the Yankees the same way the Yankee Clipper left the team (and the game) after the 1951 season, by retiring when he felt he was beginning to embarrass himself on the field, and “the game was no longer fun.”

Speculation has run over the last several years what the Yankees will do with their current icon. With all the money spent over the last three seasons on Jorge Posada, Alex Rodriguez, CC Sabathia, AJ Burnett and Mark Teixeira, the Yankees have doled out many future millions to these star players.

Will Jeter want or get similar money? Yes, he will.

That is why the Yankees will re-sign Jeter to an approximate 10-year, $200 million contract extension before, during or immediately after the 2010 season. Same length as his current deal with a little bit more money, so as not to have that Damon “pay cut” situation. Derek will then be a Yankee forever, and the long contract will eliminate all speculation about his future.

Why would the Yankees sing an aging (albeit very productive) 35 year old player to a 10 year contract?

The key to this deal is that the Yankees will not even have to pay the entire contract.

According to the MLB Collective Bargaining Agreement, if a player is placed on the Voluntary Retired list, he forgoes his contracted salary. It happened recently with Salomon Torres, who retired from the Milwaukee Brewers after the 2008 season, leaving almost $4 million on the table.

Jeter will retire well before that entire new contract will be over, and the Yankees will not have to pay the entire $200 million.

Jeter is the type of Yankee hero and dignified person that he will not let his career spiral downward to that of Willie Mays or even Mickey Mantle, guys who every else knew was done well before they retired.

Mays was a shell of his former self his last two seasons (ages 41 & 42), and should have retired after the 1971 season – on top. Mantle often said the one regret he had was he did not hit .300 for his career (he hit .298) because he held on too long. Jeter will not let that happen to him and, similar to DiMaggio, will leave well before it begins to get embarrassing.

Lets say Jeter signs that type of big contract, gives the Yankees five more good to great seasons and, while beginning to shows signs of declining productivity he reaches age 40 with about 3,700 career hits. He will be on the precipice of becoming the third player to garner 4,000 hits.

With the Yankees penchant for milestones, they will allow him to get to 4,000….if Jeter wants. If Jeter is productive enough, he will continue to play to get that number or if begins to “not be fun” Jeter will elect to bow out of the game gracefully – while on top.

Jeter has always wanted to be the shortstop for the New York Yankees and will be able to play that position as long as he wants. But if Jeter begins to decline significantly, he will not let milestones or even millions of dollars affect his decision. And he will not go to any other team, ever.

And that type of spending is different to what Damon went through with the Yankees.

First, Jeter is a home grown Yankee icon, and paying him that type of future money is a bonus as much for his past heroics and it is for future production. This is similar to how the Baltimore Orioles overpaid at the end for Cal Ripken’s services and the Chicago Cubs overpaid for Ryne Sandberg.

At that time in 1992, both Ripken’s and Sandberg’s contracts were the highest ever in baseball.

Second, Jeter is not the greedy soul that Damon appears to be, and will not stay on just to collect the money.

He has too much class for that. Grace and class like DiMaggio playing the game on the field and exiting the same game moving off the field.

Jeter will leave the game before his career has a chance to end.

6 Responses to Derek Jeter’s New Yankee Contract Should Be 10 years – $200 Million

  1. GrimSleeper says:

    This is perhaps the dumbest thing I have ever read in my life.

    • josephdelgrippo says:


      • GrimSleeper says:

        You are essentially suggesting that the Yankees commit themselves financially to an aging player at a position notorious for post-30 drop-offs in performance (the notorious MI 30 barrier) until said player is in his mid-40’s. This in itself is pointless and flat out ridiculous.

        But it gets better.

        Your suggestion is that the Yankees will not only commit to Jeter until he is 45+ years old, but (I still can’t believe I’m wasting my time even talking about this) will give him $20mil annually.

        Your justification for the Yankees to make such a ludicrous commitment: Jeter won’t stay on for the full length of the contract, but will decline when he’s “just not feelin’ it”.

        First of all, no sports organization — or any organization of any kind, for that matter — would adopt such a frankly idiotic business model. I could understand if you proposed an extension with a perpetual team or even mutual option tacked, or even a three or four year deal with a slew of mutual and/or vesting options to round it out. But to commit $20mil a year for 10 years out of pure goodwill is absolutely idiotic.

        Additionally, do you honestly think an age 42 or 43 Jeter would be worth $20mil a year? This isn’t “overpaying” like the O’s or Mini Bears did with their Hall of Famers. This is taking the entire market for middle infield and veteran talents and whizzing all over it, effectively inflating the market for mediocre and overrated talented purely because you feel like it. Which again brings me back to the plain stupidity of your suggestion from a business standpoint, but I don’t want to toil on that too long for someone who clearly lives in a world where money grows on trees.

        What’s even worse is that your fail-safe for this isn’t just that Jeter wouldn’t want to play any longer than he’s effective, it’s that he wouldn’t want to play just for the money if it ever got to that point. For $20mil. You’re telling me the man would walk away from multiple years of a $20mil salary. Even if you or me or anybody had a job more horrific than the worst vocation imaginable, we would do it for $20mil a year.

        You’ve given no provisions for the Yankees to cover their own ass when Jeter continues to ride out the contract year after year. You’ve provided no evidence for Jeter to be of any position, morally or otherwise, to put money 100% completely aside and focus only on whether or not he should be playing, and what’s worse, is you’ve based this entire waste of bandwidth out of ‘gut feeling’ and ‘reputation’ and ‘good will’. Which makes it very clear what this article is:

        A slam on that devil-spawned bloodsucker Johnny Damon.

        Your motives bleed through your words more profusely than Curt Schilling’s blood oozed through his sock. Yummy.

        This is one of the more despicable pieces of journalism I have seen in quite some time, especially from someone who lauds himself as a provider of “great baseball analyis” on such an esteemed site as BRef. I guess I shouldn’t have expected any less from someone with such audacity.

        If you want to dispute my general stroke of reality and refute, be my guest. After all, I wouldn’t want to miss the chance to lock horns with such a “great” baseball analyst.

  2. josephdelgrippo says:

    Yes, I am suggesting the Yankees will go over and above for Jeter in the next contract for more years than he will be willing to play.

    By going the mutual option route, it takes all the decision away from Jeter. Let Derek have the choice is the main point.

    He will make the best decision for all involved, and yes, if he is “not feelin’ it” as you say, or as I said, will not be embarrassed, he will leave before the contract is up.

    You mention about the “business model” and the whizzing on the “entire market for middle infield.” That is spoken like a true Andrew Friedman or Billy Beane sabermetric guru who values players based upon current or future production.

    Jeter is not some random middle infielder.

    You are taking the individual out of the equation and replacing him with a computer model of what the various stats are suggesting a player is worth.

    No, at age 42 or 43 or even 45, Jeter will not be “worth” $20 million by your probable WAR or Fan Graphs valuation, but it does not matter with a player like Jeter.

    In his next contract, he will be paid based upon past performance also, as a reward for what he has done for that franchise.

    Jeter is a much different case than all other shortstops in the game today. He is not Omar Vizquel jumping from team to team just to get another payday; or Jimmy Rollins who possibly could leave the Phillies or even Hanley Ramirez, who is probably the best hitting shortstop in the game today.

    He is Derek Jeter, captain of the best franchise in sports who has helped lead his team (the only team he ever wanted to and has played for) to five World Series titles.

    He deserves a different treatment, and not some treatment based upon a business model or WAR valuation.

    Also, our occupations will never be worth that type of money and are not relevant to Jeter’s situation. People are not dissecting every thing we do with our jobs, nor are millions of people (Yankee and baseball fans) pouring their hearts and souls into our occupations.
    If by chance, Jeter does approach 4,000 hits or even 4,256, do you think his chase for those milestones won’t be without a marketing campaign and in front of packed houses everywhere he plays?

    The milestone selling point is one reason why the Yankees overpaid for Alex Rodriguez on his new contract. In fact, a $30 million marketing agreement for the HR milestones are written in Alex’s contract.

    The Yankees will make money off of Alex’s chase for the HR record.

    If you were looking for an out for the Yankees, there it might be. But an out like that is not what is needed.

    I love the ZIPS and CHONE and other fantasy baseball projections thrown out there during the off seasons. Two seasons ago Jeter had an off year because of a hand injury. He was projected to begin his decline, but then came back last year with his arguably his best year ever.

    He heard the reports of his decline and worked hard to get better, both offensively and defensively. He was not happy with his level of play and worked hard to correct the situation.

    In regards to Damon, this was not a hit piece on him. I have done many of those already. See those others articles here:

    It is apparent you are a saber fan who uses advanced statistics to generate your ideas. I do not and that is where our difference primarily lies.

    Joe DiMaggio had a great line during his playing days. When a reported asked him why he ran hard for an outfield drive to make a catch when the game was out of reach, DiMaggio said “because their might be some people in the stands who have never seen me play before. I owe them my best.”

    That is what Derek Jeter will do and like Joe D. he will go out on top.

    With my proposed scenario, the only guarantee would be the value and length of the contract. No guarantee whatsoever that Jeter will not just sit there to collect the money long after his full time SS playing days for the Yankees are up.

    Once again, Jeter is different. If he is not performing up to standards, he will not stay around for only the payday. Jeter will walk away from one or several $20 million a year seasons.

    That will just add to his already great legacy as a team first player.

  3. GrimSleeper says:

    I appreciate the high praises you have graciously bestowed upon me with your comparisons to Mr. Friedman and Mr. Beane (no, not the weaselly one with the bugged out eyes).

    However, you are mistaken. I am not a guru of sabermetrics, nor would I ever claim to be. I merely am a practitioner of common sense, with a background in scouting, personnel operations, and, yes, baseball analytics. Statistics — especially sabermetrics — are merely a piece to an incomplete puzzle; a science that, just like any other, is constantly growing and expanding in knowledge and understanding.

    Now, as I’ve stated, I can understand if you want to give special exception to Derek Jeter. You have every right to. Heck, who would argue that you don’t want to keep the guy around at all costs? He has given more to the Yankees organization and to NYC than any sports figure in decades.

    You suggest our difference lie in our opinions on “advanced statistics”. It would be nearer the truth to state that our differences lie in our perceptions of reality (the difference being that you think in a perfect world, while I project in realistic circumstance). So lets attack this issue with a three-pronged blitzkrieg on fact and not fiction.

    First off, Derek’s value to the Yankees as a player. Fact: Derek Jeter’s production will, in fact, regress. I don’t care how much hard work you put in after hearing reports. It will happen, it has begun to happen, and it will continue to happen.

    However, Jeter’s main value lies in what he brings to both the organization as a franchise face and to the clubhouse as captain. I agree that the intent should be and will be to keep him in pinstripes for the rest of his career. But it would be irresponsible and counterproductive for the Yanks to commit themselves in both years and money to Jeter at a rate you suggest.

    I’m not saying they shouldn’t overcompensate Jeter, especially being the financial behemoths the Yankees are, but what you suggest is more than just overcompensation. It’s grossly overpaying for talent that ultimately will have more value in the clubhouse and in the public image than on the field.

    However, I’ve already covered my views on the pointlessness of basing such a mammoth risk on good will and intuition, so I won’t beat a dead horse. Onto my second point.

    It doesn’t take “advanced statistics” to evaluate the impact a significantly one-sided contract would make on a specific market. Rather, it’s a basic principal of capitalism, covered in the most basic policies of economics.

    While you may believe teams would view Jeter’s outrageously bloated proposed salary as an isolated circumstance not to be taken into consideration when evaluating financial worth, it absolutely certain that the players and agents as a whole would use the contract to their advantage. There’s no such thing as a special condition contract that does not influence its given market. Signing Jeter to an outrageously and unjustifiably large contract such as the one you propose would have tremendous impact on the league as a whole. You can be assured that the league owners would be none too happy about such a ludicrous proposition becoming reality.

    Lastly, despite your claims, it remains clear that you aim to vilify Johnny Damon, whether intentionally or not. Your admission of attacking Damon on prior occasions only weakens your case. While I understand that as a radio personality, especially in a media market such as yours, it is commonplace and borderline necessary to adopt such practices. This latest tidbit, however, is as see through as saran wrap.

    Now, my background is with small-mid market level of organizations. It’s an understatement to say that the Yankees are a totally different beast. It is my belief, however, that management of an organization must operate intelligently top to bottom, regardless of circumstance. You spend your millions on whim and good will, and the next day you end up with an albatross on your neck the likes of which can end tenures.

    I won’t continue to explain the many ways in which what your saying makes less sense than an out-of-order change machine (punny, eh?). Let me ask one question of you before I depart:

    If you do not, in fact, use any statistical consideration in your prosposals/decisions/etc., then why is it you promote your “great analysis” on Baseball-Reference, a statistical webcyclopedia?

  4. josephdelgrippo says:

    Hi Grim,

    I sent you this via regular email, but you did not respond, so I am posting here.

    Interesting that Tyler Kepner of the NY Times had a piece today which he is insinuating that Jeter’s next contract could be for ten years – similar to Alex’s 10 year deal. Kepner echoes some of my sentiments in my piece, and relating Jeter’s next deal to Alex’s incentive deal for his milestones reminded me of my email to you.

    See Kepner’s piece here:

    I sent my original Jeter piece to Dugout Central where I post some items:

    I sponsor some pages at BR becasue it brings a few people to my blog, which I wish I had more time to write more. The BR site gives all stats, not just SABER ones.

    A full time job outside sports does not lend it self to much time at the keyboard.

    Check out some pieces I wrote here, including a few on Damon:

    If you check out the best power hitters in baseball you will notice that their OPS when putting the ball in play on a 0-0 counts are usually over 1.000. But when putting the ball in play at that count, they don’t walk much and never strike out. But they do punish the pitcher.

    First and third, I want my slugger ripping at the first good pitch he sees, not working the count!

    I am sorry if that doesn’t get a pitchers pitch count up, but my idea is to knock him out of the game instead of pitch count him out. It has much more mental appeal to pound a good pitcher instead of pitch count him to death.

    If a pitchers job is to “get ahead” and all the good pitchers do that, why take pitches early? I just do not understand it. Too many hitters can not hit well when behind in the count. They usually swing at bad pitches then, and get themselves out.

    I research the saber stats some, but do not put much into the entire Moneyball theory (I believe Billy Beane is not a good judge of talent, just a number cruncher) that a guy with a high OBP is necessarily better than someone with a lesser OBP but does more things better. The game of baseball is stat oriented, but much more than just numbers. Players have to know how to play the game to win individual games, not just look good number wise at contract time.

    Isn’t that the idea of playing, to win the game?

    OBP is important, but you need guys to drive the baserunners in. Walks are an important part of the offensive side of the game, but not to where you don’t swing at good pitches in the strike zone. There are times to be patient and times to be aggressive in the batters box. I bet that Carlos Beltran wishes he was more aggressive in the 2006 NLCS Game 7 9th inning at bat. That first pitch from Adam Wainwright was right down the dick, and he sat there and looked at it.

    Except for 17 games in baseball history both teams in every game played have gotten men on base. Last year the average WHIP in baseball was around 1.5, so each team averages about 13-14 guys on base every game.

    What do those teams do when guys get on base is of utmost importance. That is why RBI’s are so important. No pressure in getting on base, but lots of pressure hitting when guys are on base.

    You said you have a background in scouting.

    So who do you work for?

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