The Oldest $100MM Players

Kevin Brown signed the first nine-figure deal in baseball history after the 1998 season. 33 at the time, Brown had just logged 257 innings for the NL Champion Padres, striking out 257 and posting a 2.38 ERA (164 ERA+). Brown provided the Dodgers with some elite seasons before moving to New York, where he disappointed in pinstripes. 

In the decade-plus since Brown finalized his record deal, all of the 30-plus players to sign for $100MM or more have been younger than 33. Here's the complete list of $100MM players sorted by age, courtesy of MLBTR’s Transaction Tracker (the list includes free agent signings and extensions, but does not include posting fees for Japanese players):

  • Kevin Brown, 33, signed a seven-year, $105MM deal on 12/12/1998.
  • Alex Rodriguez, 32, signed a ten-year, $275MM deal on 12/13/2007.
  • Cliff Lee, 32, signed a five-year, $120MM deal on 12/13/2010.
  • Jayson Werth, 31, signed a seven-year, $126MM deal on 12/05/2010.
  • Albert Pujols, 31, signed a ten-year, $240MM deal on 12/08/2011.
  • Ken Griffey Jr., 30, signed a nine-year, $116.5MM deal on 2/11/2000.
  • Jason Giambi, 30, signed a seven-year, $120MM deal on 12/18/2001.
  • Alfonso Soriano, 30, signed an eight-year, $136MM deal on 11/20/2006.
  • Carlos Lee, 30, signed a six-year, $100MM deal on 11/24/2006.
  • Ryan Howard, 30, signed a five-year, $125MM extension on 4/26/2010.
  • Matt Holliday, 29, signed a seven-year, $120MM deal on 1/7/2010.
  • Carl Crawford, 29, signed a seven-year, $142MM deal on 12/8/2010.
  • Mike Hampton, 28, signed an eight-year, $121MM deal on 12/12/2000.
  • Manny Ramirez, 28, signed an eight-year, $160MM deal on 12/19/2000.
  • Vernon Wells, 28, signed a seven-year, $126MM deal on 12/20/2006.
  • Barry Zito, 28, signed a seven-year, $126MM deal on 12/29/2006.
  • Johan Santana, 28, signed a six-year, $137.5MM deal on 2/2/2008.
  • C.C. Sabathia, 28, signed a seven-year, $161MM deal on 12/20/2008 (revised as a 31-year-old on 10/31/2011). 
  • Adrian Gonzalez, 28, signed a seven-year, $154MM deal on 4/15/2011.
  • Jose Reyes, 28, signed a six-year, $106MM deal on 12/04/2011.
  • Mark Teixeira, 28, signed an eight-year, $180MM deal on 1/6/2009.
  • Todd Helton, 27, signed a nine-year, $141.5MM deal on 3/1/2001.
  • Carlos Beltran, 27, signed a seven-year, $119MM deal on 1/13/2005.
  • Ryan Braun, 27, signed a five-year, $105MM deal on 4/21/2011.
  • Matt Kemp, 27, signed an eight-year, $160MM deal on 11/14/2011.
  • Prince Fielder, 27, signed a nine-year, $214MM deal on 1/24/2012.
  • Ryan Zimmerman, 27, signed a six-year, $100MM deal on 2/26/2012.
  • Derek Jeter, 26, signed a ten-year, $189MM deal on 2/1/2001.
  • Joe Mauer, 26, signed an eight-year, $184MM deal on 3/21/2010.
  • Troy Tulowitzki, 26, signed a six-year, $119MM deal on 11/30/2010.
  • Alex Rodriguez, 25, signed a ten-year, $252MM deal on 12/1/2000.
  • Albert Pujols, 24, signed a seven-year, $100MM deal on 2/19/2004.
  • Miguel Cabrera, 24, signed an eight-year, $152.3MM deal on 3/24/2008.

Full Story | 25 Comments | Categories: Uncategorized

25 Responses to The Oldest $100MM Players Leave a Reply

  1. Must be a slow day.

  2. baseballa11 3 years ago


  3. Mike1L 3 years ago

    mixed bag.  like throwing darts with your off hand.  might take a ding out of the wrong place

  4. Lunchbox45 3 years ago

    Isn’t this just the entire list of 100mm players? 

    • tacko 3 years ago

      Ordered by age when signed. Misleading title, I guess.

  5. daveypinstripes 3 years ago

    I actually liked the post. Not a lot of success out of those contracts, esp. with guys around 28 or older. Yikes. 

  6. An amazingly large number of these look like amazingly bad deals…

  7. johnsilver 3 years ago

    What were/are projected to be the best deals on that list?

    Griffey jr

    Worst deals are too numerous and may cause a flame-thrower bonanza…

    • Lunchbox45 3 years ago


      I’d Say Cabrera, Pujols (cards deal), Jeter.

      • johnsilver 3 years ago

        Almost listed Cabrera. his glove at any position worse than Ramirez, but yeah.. his bat is a no doubter. yes on tex. NY got a complete player, or will. produce runs, get on base. Power and one of the best with the glove at his position.

        Not because of playing for NY left off jeter, Just hard to give anyone who is not a huge run producer an average of almost 20m over 10 years. Then..Maybe it’s just me and yeah.. I know CC and Reyes got it also. LOL

        Must have missed Pujols.. A 100% no doubter the Cardinals contract.

        • Lunchbox45 3 years ago

           Jeter was worth an average of 4.8 WAR over the course of that contract. hard to argue with that.  He was paid handsomely but he was pretty consistent both in terms of performance and health.

          Teix I don’t agree with, he rebounded nicely from a tough 2010, he might end up being worth the contract but i don’t see it as one of the best.   Then again on this list I guess coming close is pretty substantial

          • NickinIthaca 3 years ago

            I also think that Jeter is one of the players whose contract isn’t justified only by his play on the field.  The guy has been a class act on and off the field, has sold a ton of Yankees merchandise and is one of the most omnipresent (and likeable) players of the last twenty years, regardless of what team you root for. 

            Add that to his play on the field (which if I’m not correct an average of ~5 WAR would mean that he was worth ~$20 million/year through the course of the contract), his leadership and other intangibles, and it makes sense to me why he received the last contract he did.  He is one of the few players that it makes sense to pay (within reason) for his past as well as what they were expecting for the future.

          • monkeydung 3 years ago

            i don’t care about his attitude or intangibles, but the dude sells enough merch and tickets that it’s worth it for the dodgers.

        • jeffmaz 3 years ago

          A ten year deal at the age of 31 is a doubter.

          • NickinIthaca 3 years ago

            He’s talking the Pujol’s Cardinals contract, not the new one with the Angels….

    • A-Rod’s first nine figure deal is easily the best on the list, right? He was also one of the youngest to hit free agency.

  8. MetsMagic 3 years ago

    I’m still trying to find how giving Carlos Lee or Mike Hampton $100 million at any age was once a good idea. 

  9. Whole_New_World 3 years ago

    The Mauer deal is really starting to look fairly godawful.

    Amazing the first 20 comments did not mention the Barry William Zito deal, the mother of all disasters.

  10. Mostly Yankees – shocker!

  11. ronny9 3 years ago

    I count 33 contracts total. Of those 33 deals, 14 are really tough calls on whether we can even make a judgement on a very very small % of the contract having happened yet. 

    The 14 i don’t think you can judge are obviously the deals from this offseason, last year and a couple longer term deals from a couple years back: Lee, Werth, Pujols, Howard, Holliday, Crawford, Adrian Gonzalez, Reyes, Braun, Kemp, Feilder, Zimmerman, Mauer, Tulowitzski (yes some of these deals don’t look promising, but in fairness lets move on for now)

    So you can only really judge the other 19 contracts that are at least 35 % complete (in my opinion).

    Of those 19 contracts, only SEVEN deals (again in my opinion) are deals that worked out to the benefit of the team and not just the player: Manny Ramirez, CC, Jeter, ARod’s first deal, Pujols’ first deal, and Miguel Cabrera are for sure deals that seem to have worked out favorably for the team. As a sox fan it hurts but, i have to say that Texiera’s deal looks OK at least to this point as well, although he better age well for it to remain looking promising. 

    The other 12 deals are all terrible.  So that’s a success rate of 37%, and therefore over 60% of these deals blow up in the face of the team.  I think most of us knew the majority of huge deals didn’t pan out for the team, but after looking at it on a case by case basis i was surprised that roughly 2 of every 3 deals failed.  Scary really. 

    I think its also important to note that to this point, the deals that i think are hard to judge, 50% of those also seem questionable at best include Werth ( Huge overpay), Pujols (age), Howard (huge overpay), Crawford (disappointing), Reyes (health), Fielder (body type at age 34 thru 36 might be questionable), Mauer (health)

  12. Lunchbox45 3 years ago

    or sticks out like a sore Vernon Wells

  13. NickinIthaca 3 years ago

    I thought it was a sore elbow?


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