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Big Money Deals We Never Saw Coming

By Tim Dierkes | April 17, 2020 at 1:22am CDT

In today’s video, Jeff Todd explores the MLB free agent deals that have absolutely floored the MLBTR writing staff. Stick around until the end to see which one stunned us the most!

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Cincinnati Reds MLBTR On YouTube Mike Moustakas

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2020-21 Free Agent Class: Shortstops
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68 Comments

  1. dynamite drop in monty

    5 years ago

    So much better than Lugooooooo… Scu Scu Scutaro!!!!

    Reply
  2. Phiilies2020

    5 years ago

    Jordan Zimmerman? Eric Hosmer? Bryan Shaw?

    4
    Reply
    • lowtalker1

      5 years ago

      Big money was on all thoughts on hosmer it just depended on who got him

      Reply
    • jdgoat

      5 years ago

      Zimmermann actually got less than what was predicted and I think Hosmer might have as well.

      1
      Reply
  3. Rangers29

    5 years ago

    Jordan Lyles surprised me this off-season. Yu Darvish even surprised me a little bit when he signed.

    2
    Reply
    • brandons-3

      5 years ago

      Darvish’s contract was odd because free agency has transitioned to “Unless you are the elite of the elite, you aren’t going to command what you may have 10-15 years ago.”

      Too many examples of nine-figure deals going south the more a pitcher creeps into their 30’s. Teams just aren’t as willing to shell out money unless there’s a Gerrit Cole on the market.

      Reply
  4. wild bill tetley

    5 years ago

    Stephen Drew’s $9.5 million from the Red Sox in 2013 after posting a .657 OPS and 81 OPS+. 2011 wasn’t all that much better.

    2
    Reply
  5. Rangers29

    5 years ago

    Oh I got another one, Zack Cozart’s contract with the Angels after his one good season.

    4
    Reply
    • SpiderManFromMars

      5 years ago

      For sure – I was on my down to comment the same thing. Coming off his 2017 season, I could kind of see a team over spending a little if he were 28 and a team needed a SS…..but he was 32 and the Angels already had Simmons.

      Reply
  6. phillyballers

    5 years ago

    Bobby Bonilla turning 5.8M into 29.8M

    4
    Reply
    • findingnimmo

      5 years ago

      Ughhhh

      Reply
    • wild bill tetley

      5 years ago

      Bonilla’s agent should be inducted into the Baseball Hall of Fame in the builders wing.

      2
      Reply
  7. chri

    5 years ago

    Jacoby Ellsbury’s Yankees contract? He had injury issues as a Red Sox and 2011 was his only year he was a superstar.

    Reply
    • luckyh

      5 years ago

      That one was my favorite.

      Reply
    • Eatdust666

      5 years ago

      I’m honestly surprised that it wasn’t even mentioned in this video.

      Reply
  8. pinkerton

    5 years ago

    Peter O’Brien and his rave reviews

    Reply
  9. Ejemp2006

    5 years ago

    How is Miguel Cabrera not number one on the list? His extension was way before necessary and way more money and years than expected.

    Reply
    • dynamite drop in monty

      5 years ago

      Because he’s awesome.

      Reply
      • seattlesuperfan

        5 years ago

        Was*

        2
        Reply
    • Johnny

      5 years ago

      Because jeff was looking at free agent deals not extensions

      2
      Reply
  10. jgreen2487

    5 years ago

    Funny.. every article I read says moustakas was signed to about what he was estimated to be worth .. quick google search on his contract shows that.

    1
    Reply
    • dynamite drop in monty

      5 years ago

      FART

      Reply
      • thebaseballfanatic

        5 years ago

        Well then…

        1
        Reply
    • thunderroad19

      5 years ago

      MLBTR is bewildered about Moustakas’ contract because they missed it so badly. It’s likely to be 1 season too long to be worth 16M per but most teams allow for that. Moose is one of those no nonsense guys who brings more to a team than smartphone stat geeks understand.

      1
      Reply
    • SalaryCapMyth

      5 years ago

      Every article? You wanna post a link to verify your claim?

      Reply
  11. Ketch

    5 years ago

    Gary Mathews Jr

    1
    Reply
  12. Marksman18

    5 years ago

    Yasmany Tomas.. 6 Yr 68 million.

    Reply
    • Brixton

      5 years ago

      That was actually a discount at the time bcuz he wanted the opt out

      Reply
  13. Marksman18

    5 years ago

    Martin Prado..

    Reply
    • sandman12

      5 years ago

      You drilled it. Prado’s $40m was utterly inexplicable.

      Nathan Eovaldi’s contract with Boston was outlandish as well.

      1
      Reply
  14. MoRivera 1999

    5 years ago

    I don’t recall whether anybody saw it coming or not but Carl Pavano had exactly one good year (18-8, 3.00 ERA) and parlayed that into a 4 yr/40MM contract with the Yankees in 2004. He was injured most of the time and finished 9-8 over the 4 year life of the deal.

    Reply
  15. angt222

    5 years ago

    Oliver Perez- 3yrs/$36M..

    Reply
  16. brucenewton

    5 years ago

    Pomeranz. Highest paid lefty specialist ever, then Manfred devalues lefty specialists the next day.

    Reply
    • Ashtem

      5 years ago

      Didn’t you see Pomeranz dominate in Milwaukee?

      Reply
      • bdpecore

        5 years ago

        You mean in the 26.1 IP down the stretch? I know he was good but that’s a very small sample size to go off of to dish out a 4yr/$32MM deal. Heck most relievers never sniff a four year deal unless they are proven elite closers over multiple seasons.

        Reply
        • 4WSsince04

          5 years ago

          San Diego had Pomeranz before and knew what they were getting. He pitched pretty well there and it is a pitcher friendly park, but still way over paid.

          Reply
  17. findingnimmo

    5 years ago

    Jason bay to the Mets
    Pavano to yanks
    Samardjza (spelling) and zito to giants
    Just a few I can think of right away.

    Reply
    • dugmet

      5 years ago

      Bay’s contract was not unexpected. He had an MVP caliber year in Boston and was an A.S. in Pittsburgh. His demise however was unexpected – but not the contract.

      Reply
  18. justdadamaja

    5 years ago

    Zack Wheeler to the Phils for 120 mil/5

    3
    Reply
    • Brixton

      5 years ago

      How

      Reply
      • Ejemp2006

        5 years ago

        Wheeler is not as good or durable as Porcello. And yet that contract… Wheeler’s contract will be the next Zimmerman contract and be an absolute 100 million dollar waste.

        Reply
    • MoRivera 1999

      5 years ago

      In that market for SP’s, when he was #3 among available SP’s, can’t see that. Of course he was going to get a big payday. Of course.

      Reply
      • Lanidrac

        5 years ago

        He was #3 by a very wide margin from #2 and not very far ahead of whomever you would consider to be #4.

        Reply
  19. yanks23

    5 years ago

    Rusney Castillo

    Reply
  20. df08988

    5 years ago

    Chris Sale’s extension with Sox?

    Reply
    • AtlSoxFan

      5 years ago

      Sale is looking like a bad decision in the short term, BUT, wasn’t unexpected at the time. Question was would boston pay him or someone else.

      Reply
  21. threed75

    5 years ago

    Homer Bailey?

    1
    Reply
    • schellis 2

      5 years ago

      Bailey was fine. His contract was around what pitchers of his caliber were getting. He was trending upward and hadn’t had any injury issues in the years prior. You can’t predict injuries.

      People act like the reds have a 30 plus year old coming off multiple lost seasons that contract.

      Yes it was a bad deal once it played out but it wasn’t at the time it was signed.

      Now ryan Howard or the second Cabrera contract those had very little chance of being good.

      Reply
      • jgreen2487

        5 years ago

        Some of the worst luck the reds could have gotten. It might not have been a bad contract at the time, but if (at the time) the reds weren’t trying to play the conservative route they should have resigned Cueto.

        Reply
    • wild bill tetley

      5 years ago

      Bailey was a huge shock. He was going to get paid. Not THAT much.

      Reply
  22. Lanidrac

    5 years ago

    A-Rod’s free agent deal with the Rangers? Sure, that first deal (up until he opted out) was actually worth it, and his later extension with the Yankees was objectively much more ridiculous, but I don’t think anyone at the time expected A-Rod to get such a huge record-breaking (by such an order of magnitude) deal in free agency, whereas it was largely expected that the Yankees would break the bank in order to keep him.

    Reply
    • BlueGreatDane

      5 years ago

      How was Arods first contract a “big money deal no one saw coming”? Literally everyone knew a huge deal was coming, several years in advance. Speculation of breaking the $200M barrier was not uncommon.

      Reply
      • Lanidrac

        5 years ago

        A huge deal, yes, perhaps even $200M+, but nobody expected him to get anywhere near $252M.

        Reply
  23. Lanidrac

    5 years ago

    Jason Heyward? Even if his offense hadn’t declined, he had had only one exceptional offensive year, and a glove-first right fielder was never going to be worth as much as he got.

    3
    Reply
    • seth3120

      5 years ago

      But he had youth and two other teams offered just as much. Bad contract no doubt but I wasn’t shocked in the least

      Reply
  24. Eatdust666

    5 years ago

    Kei Igawa

    Reply
  25. TJECK109

    5 years ago

    Giancarlo Stanton or Harper

    Reply
  26. vincent k. mcmahon

    5 years ago

    I saw moose getting big money, just nowhere over the 64mil he got.

    Reply
    • wild bill tetley

      5 years ago

      With a move to 2B permanently on-top of that.

      Reply
    • Ejemp2006

      5 years ago

      The Reds hope Moose can be what Jason Werth was to the Nats, a vet who teaches all the kids to prepare like pros and expect to win. I saw it coming but hoped the Padres would have pulled it off.

      Reply
  27. dugmet

    5 years ago

    ian desmond.

    Reply
    • wild bill tetley

      5 years ago

      I think Desmond was going to get big $$. People forget he apparently declined 7 years/$107-mil with Washington.

      Reply
    • Lanidrac

      5 years ago

      The more surprising part was signing him to play 1B.

      Reply
  28. James1955

    5 years ago

    Heyward. Bad signing at the time. Worst contract in history.

    Reply
    • BlueGreatDane

      5 years ago

      Chris Davis says hi.

      2
      Reply
    • wordonthestreet

      5 years ago

      Heyward signing not even close to worst contract

      Reply
  29. BlueGreatDane

    5 years ago

    The Yankees giving $80+ million to AJ Burnett was always a huge head scratcher to me.

    That happened. They gave AJ Burnett $80 million smackers.

    Reply
  30. JrodFunk5

    5 years ago

    Pablo Sandoval and Hanley Rameriz were considered bad deals at the time and turned out even worse than imaginable

    1
    Reply

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