Derek Jeter could be making $25 million per season right now


2006 Jeter would have cashed in (Julie Jacobson/AP)

The baseball hot stove season is rife for what-if scenarios. One of the most popular right now questions how the Derek Jeter situation would have unfolded had he produced a 2010 season more in line with his career numbers. Would there be adequate pressure for the Yankees to offer a fourth, or even fifth, year? Or would other teams be just as reticent to sign a 37-year-old shortstop? While these questions are interesting enough, they’re not nearly as interesting as another what-if. Ben hinted at it earlier in the month, and William mentioned it more explicitly in a recent post at The Yankee U. Where would the Yankees be right now if Derek Jeter had signed a long-term contract after the 1999 season?

At that point in his career Jeter had all the leverage in negotiations. He was heading into his age-26 season and had produced two tremendous seasons in 1998 and 1999. In ’98 he had a .385 wOBA and produced 7.8 bWAR, which was just 0.1 behind Alex Rodriguez for the league lead. That landed him third in the MVP voting. His 1999 follow-up was the greatest season of his career. His 8.0 bWAR was tied with Manny Ramirez for second in the league — Pedro Martinez produced 8.3 WAR in his historic season. Yet the voters discounted Jeter, voting him sixth when he probably should have won the damn thing. Still, the numbers were there. The Yankees were going to have to pay Jeter.

What made Jeter’s run all the more remarkable was that he still had two years of arbitration left. The Yankees sought to buy out those, plus five years of free agency, with a seven-year, $118.5 million offer. The Jeter camp was apparently ready to pay, but George Steinbrenner wouldn’t sign off on the deal. The Yanks instead paid Jeter a $10 million salary in 1999 before eventually signing him to the infamous 10-year, $189 million deal, which came as a direct result of Alex Rodriguez’s 10-year, $252 million contract. It would appear that failure to execute the contract one year prior ended up costing the Yankees $80.5 million (the $10 million 2000 salary plus the $189 million contract, minus the $118.5 original). Yet that leaves the story short by four years.

Had Jeter signed that contract he would have been eligible for free agency after the 2006 season, which was another marvelous year. Jeter produced a .399 wOBA on the power of a .343 BA and .417 OBP. To put that in perspective, Jeter’s gross offensive numbers amounted to 41.8 batting runs above average — which factors in playing time and park, but not position. That ranked sixth in the AL. The only players ahead of him were 1B/DH/OF types. This was enough for 6.2 WAR, which ranked second behind Grady Sizemore. I’m not sure why the baseball writers were infatuated with Justin Morneau that season, but Jeter probably should have won the MVP. And had the Yankees executed his original extension, he would have taken that hardware into free agency.

The situation then would have been the same as the situation now, in that both sides need each other. The difference, of course, is that then Jeter was a 32-year-old coming off a career year. Now he’s a 36-year-old coming off the worst season of his career. Chances are the Yankees aren’t going to go far above their three-year, $45 million offer. Maybe sentiment turns that into $60 million, but I very much doubt it. Unless Jeter picks up his ball and signs with another team for less, he’ll end up having made $250 to $260 million with the Yankees. He would have made much more if he had become a free agent after the 2006 season.

Through the 1999 season Jeter had earned $6.43 million. Then add in the $118.5 million through 2006. That puts him at just under $125 million before he hit free agency. The economy was booming in the winter between 2006 and 2007. Barry Zito got seven years and $126; Carlos Lee got six years and $100 million; Alfonso Soriano got eight years and $136 million. Derek Jeter would have gotten more than all of them. I’m betting he would have matched Soriano’s eight years, which would have kept him around through age 40. I’m also betting he would have easily topped $20 million per season — perhaps all the way to $25 million. Splitting the difference, the contract would have been worth $180 million, and would have paid Jeter through 2014. His career earnings would then have been $305 million.

Sometimes these things end up working out for the better. There is simply no way that Jeter will cross the $100 million mark with his new contract. In that way, the Yankees will have saved money with the 10-year, $189 million contract. While the seven-year deal proposed after 1999 looks better because of the shorter term and lower average annual value, it would have given Jeter one more chance at a big pay day. With his status among Yankees fans, his age, and his stellar 2006 season, he would have cashed in considerably. While the negotiations for his next contract aren’t exactly smooth, they’re certainly preferable to paying Jeter north of $20 million per season for the next four years.

Categories : Days of Yore
  • YankeesJunkie

    That is an interesting take on how the Yankees will most likely end up paying Jeter less with Steinbrenner balking on that deal that ended up costing them 70 million and three more years. At this point in his career Jeter just won´t get the 4 years or the 20 million a year and when he realizes that he will sit down with the Yankees and make a deal probably 3/50-55 and everybody can walk away happy. At this point I think it is time to take zen baseball and transfer to zen negotiations where us as fans just watch the wheelings and dealings unfold ultimately knowing that Jeter will end up most likely signing a three year possibly four but doubtfully contract around 17 million a year and root him on to 3000 hits.

  • Monteroisdinero

    So will his enormous pride lead to re$entment and bitterne$$ from this negotiation that will translate to on the field issues?

    • The Big City of Dreams

      You bet it will lol

  • I am not the droids you’re looking for

    With PEDs basically off the table now (NOT suggesting in the slightest that Jeter was a user) and bodies breaking down at a more historically normal time frame, I wonder if agents and players will increasingly strategize to end contracts by say the age 34/35 seasons, during which it’s more likely that a player would have a very good year (and hence a shot at one more lucrative medium term deal) than the age 36/37 seasons, by which time most players will have likely started declining more steeply.

    Always tough to turn down a bird in hand of course, so as long as teams offer fat contracts that last late into the players’ 30s best guess is players will continue to take them!

    • Zack

      I can players wanting more opt-out clauses, but no way they’re giving up 2 years of guaranteed money with all the variables involved.

      • I am not the droids you’re looking for

        Ah yes I hadn’t considered the opt out clause (Fail on my part!)

        The question is will teams be increasingly likely to give them, or less so? Maybe more mutual options in out years instead?

        • Zack

          The only thing positive about an opt-out for a team is that you get a healthy/productive player until he’s say 33, then you let another team pay him for his ‘down’ years.

          But say CC opts out next year, Pettitte retires, and AJ doesn’t bounce back, then it’s Lee & Phil and the Yankees would have to give CC a new/longer contract, which extends the risk.

  • UnNamed Yankee Source

    Intensives….Is there a limit?

    Could the Yanks in theory offer Jeter a 3/30 deal, with..
    Bonuses that could net Jeter an extra 10-15 per year, some easily attainable to get him an extra $5mill and others based off his average stats?

    Perhaps if he reaches certain goals, he can opt out and renegotiate his deal or guarantee pay increases in following years?

    • JobaWockeeZ

      Against the rules. Only PA’s are allowed in an incentive laden deal.

      • UnNamed Yankee Source


        • Plank

          Plate Appearances.

          Bonuses can also be given for games started or innings pitched. Anything that is about the amount played and not performance can add to salary.

        • JobaWockeeZ

          Plate appearances.

      • the Other Steve S.

        So is ARod’s deal somehow different, with payoffs for milestones?

        • I am not the droids you’re looking for

          We’ve not seen the specific language on these home run bonuses, but word was that somehow the language was tied to “marketing” or some such related to the home run plateaus, rather than to the home runs directly.

          Seems like a spirit of the law violation to me but what do I know?

          • Benjamin Kabak

            MLB signed off on the bonuses in A-Rod’s deal though. But I don’t think they want to make it a practice to allow deals like A-Rod’s.

            • Plank

              Yeah, I think the player’s association could have voided the contract since they don’t want performance pay to become to norm, but the Arod contract was so valuable they allowed it anyway.

  • steve (different one)

    Since the “expiration” of Jeter’s alternate universe contract, Jeter has hit .306/.374/.423 for a 110 OPS+. Those are obviously very strong numbers for a SS, but they are not “top 3 salary in MLB” numbers. Esp if we consider the 800 lb gorilla skin glove Jeter wears in the room.

    Now think about that going forward. Those numbers consist of close to 3000 plate appearances. While I expect a moderate bounceback next season, what is the best case scenario over the next 3 years? 100 OPS+?

  • UnNamed Yankee Source

    Could they then write a contract that is a:

    2 year $36 mill deal with a mutual option for a 3rd year at $15 mill?
    - or –
    3 year $50 mill ($25/$15/$10 mill) deal with an opt out after year 1?

    • vin

      They could, but Jeter is looking for more. In these situations, the player will almost always want the additional year(s) tacked on to the deal. The Yanks would probably be fine with paying him 3/60 – but the easiest way for the player to get more money is with the extra year, even if its a lower average annual value.

      My guess is Jeter is looking for 4/80. Those 4 years will almost certainly cover his final 4 years where he is a productive player. And Derek will get a slight, but not unnoticed, raise per year.

      The 24-25 million per year stuff was just part of the negotiations. The difference between the two parties is in adding that 4th year.

  • Jimmy McNulty

    Oh the Dodgers are close to signing Uribe, so there goes options for both parties involved.

    • bexarama

      Three years, lolwut

      • vin

        Welcome to the Wacky World of Ned Colletti.

        • Rob

          What do you mean? The Dodgers signed Uribe for three years at $21 million for the same price the Yankees may end up paying Jeter for one year! I doubt the Yankees will go up to $21 million a year for Jeter, but in the Wacky World of Jeter-Land, who knows.

          This does remove one alternative landing spot for Jeter, playing in a major media market and for Don Mattingly. Yet it also further opens up the SS slot in SF. Yet would SF let Uribe walk for $7 million a season for three years and sign Jeter for $18 million a season for four years? No way.

      • Jimmy McNulty

        Yeah hopefully this will speed up the process, though it sets a bad market precedence for Jeter’s next contract.

        • Rob

          What’s the bad precedent? Uribe was the only available SS who had a higher WAR than Jeter, 3.2 to 2.5. He’s also more flexible on position. He is a bit short in the iconic and intangibles categories that Jeter’s agent is trying to push, but by signing for $7 million a season, Jeter now has to argue he’s worth more than three times that to get his $23 million per.

      • Jimmy McNulty

        3/21 per Rosenthal. Derek Jeter won’t be a Dodger. Thankfully, Juan Uribe won’t be a Yankee.

  • nathan

    That Big Stein, i am sure he didnt know at that time abt this, but his balking lead to Ms saved now.

    I still cant believe how not one MSM article is going after DJ.

    For utter comedy, check this Lupica rant on ESPNNY:

    I reside in the west coast and got to listen to FosSportsRadio (way better than WFAN lineup – not saying much) and one of the late night hosts said Yankees should fire Cashman for “Conduct detrimental to the Yankees” for saying “shop this offer” and “insulting DJ”. The host btw is a Yankee fan, thats why I listen to his show sometimes. Comedy.

    • mike c

      What has jeter done that the media should be ‘going after’ him for? it’s a baseball negotiation and his agent is doing his job. sounds like you just want to read hating on jeter

      • nathan

        Far from it. I just want him to realize what his true worth is and fair commentary on his true worth. I think that is leagues away from hating on someone.

        • mike c

          everything ive seen backs up the yankees offer to jeter and that he’ll be overpaid in terms of production. what’s left to be said at this point?

    • steve (different one)

      Actually, I think the media in NY has been shockingly in the Yankees’ corner. Lupica is a moron, but I have not seen a lot of the “pay him whatever he wants” articles that I was expecting.