Who Could Get The Next Mega-Extension?

In extending Ryan Braun and Troy Tulowitzki through the year 2020, the Brewers and Rockies made bold commitments to their young stars by adding multiyear extensions on top of pre-existing contracts that already covered both men through 2015 and 2014, respectively. 

Are these deals risky?  Absolutely, but the contracts represent the latest step in how clubs attempt to lock up their young stars.  It isn't enough to just gain cost-certainty on a player through his arbitration and first few free agent years.  If a team feels they have a true franchise player, it won't hesitate to sign that player to what essentially could be a lifetime contract in order to (hopefully) avoid spending even more money to re-sign that player or a comparable star as a free agent.

Should other clubs look to explore this tactic of extending an extension, here are some of the possible candidates to join Braun and Tulowitzki in the "2020" club.

  • Evan Longoria.  We start off with the man with arguably the most team-friendly extension in baseball history.  Longoria's six-year, $17.5MM contract signed in April 2008 contains three team option years (worth $7.5MM, $11MM and $11.5MM, respectively) that could keep him in Tampa Bay through 2016, his age-29 season.  As MLBTR's Mike Axisa pointed out over the winter, however, the Rays' uncertain financial situation makes it unlikely that they would make an even longer commitment to Longoria than they already have. 
  • Robinson Cano.  Cano signed a four-year, $30MM extension before the 2008 season that also includes team option years for 2012 ($14MM) and 2013 ($15MM).  New York will obviously keep Cano in the fold through his age-30 season by picking up those two options, unless those years get replaced by a longer-term contract.  Cano hired Scott Boras as his agent in February and while Cano said he isn't planning to ask for an extension before his current deal expires, the second baseman is clearly already thinking ahead.
  • Justin Upton.  The first overall pick of the already-legendary 2005 draft is signed through 2015 on a six-year, $51.25MM extension that will run out when he's 28 years old and right in the middle of his prime years.  The Diamondbacks explored a few deals for Upton over the winter and set off a flurry of speculation, but it appears as if GM Kevin Towers was simply doing his due diligence to see if another team would go overboard with a trade offer.  Upton had a slightly disappointing (.799 OPS) 2010 season, so Arizona might wait for at least one more superstar campaign from their young star to make sure he's worth the risk of another multiyear extension.
  • Hanley Ramirez.  It seems odd to think of the Marlins doling out any major extensions, let alone two to the same player.  With the team moving into its new Miami ballpark next year, though, the extra revenue could make another multiyear deal for Ramirez into a reality — not to mention generating some goodwill amongst Marlins fans to get them to spring for season tickets. Ramirez is under contract through 2014 on a six-year, $70MM deal and 2015 will be his age-31 season.  If Florida did explore an extension for Ramirez, they would surely have to factor in a move away from shortstop, since his defensive woes (a career -9.4 UZR/150) are likely to worsen as he ages.
  • Ryan ZimmermanMLBTR's Ben Nicholson-Smith recently outlined how the Nationals' previous extension with Zimmerman — a five-year, $45MM pact that runs through 2013 — was a terrific bargain for the club.  Given Zimmerman's production, age (he'll be 29 when his deal runs out) and Washington's willingness to spend, Zimmerman is probably the most likely player on this list to receive a Braun/Tulowitzki-esque deal.
  • Joey Votto.  The Reds took the first step towards locking up the reigning NL MVP when they signed Votto to a three-year, $38MM pact that covered the first baseman's arbitration years.  Votto is still on pace to hit free agency as a 30-year-old in his prime, and as one agent put it, "the Reds took on all the risk" with this initial deal.  Cincinnati has put itself in position to contend over the next few seasons, so that will theoretically take care of the Great American Ballpark's attendance problems and make it possible for the team to get Votto signed to an even longer-term contract.
  • Miguel Cabrera.  Cabrera signed an eight-year, $152.3MM extension with the Tigers before the 2008 season.  He'll turn 33 in 2016, and that advanced age plus his off-the-field issues make him an unlikely extension candidate.  Detroit has the money and Cabrera has put up Cooperstown-worthy numbers throughout his career, but there just may be too much risk involved for the Tigers to commit more money to the slugger.

68 Responses to Who Could Get The Next Mega-Extension? Leave a Reply

  1. notsureifsrs 4 years ago

    won’t be longoria because the rays are smart instead of stupid. they’re very avante-garde that way

    won’t be cano because the yankees don’t have to

    i can see jocketty jumping on board like a fool. but votto’s actually a better player to invest in than braun

    • SplitFingeredPujol 4 years ago

      Yeah the Rays simply don’t have the financial muscle to be taking any kinds of risks in terms of baseball’s economy down the road. They can really only make long terms deals if they’re overtly team friendly and won’t totally handcuff the team if it doesn’t pan out. Low risk, essentially. I feel for that team and (limited) fanbase. They really need to move. They were maybe the most exciting team in the game for a couple years and yet nobody cared. I feel for the fans in Tampa that DO care, but they need to get the hell out of there.

      • JacksTigers 4 years ago

        Your user name made me sick to my stomach.

        • SplitFingeredPujol 4 years ago

          It was either this, or Lincecum_Stains

      • chuckables 4 years ago

        Agreed. Read The Extra 2% by Jonah Keri. The fans are fine and extant. However, that park has the lowest percentage of people within 30 min of the ball park. The Yankees and Mariners are in the same relative market as the Rays. The difference: The Rays have THE SMALLEST percentage of people who live within 30 minutes of the ball park. That albatross of a ball park is only restricting a new revenue stream. Put a brand new park in that same location and you’ll have the same bad attendance. You can’t blame the owners. You can’t blame the fans. You can go as far as not blaming the ballpark. What you can blame is the location of the ballpark and the difficulty of driving there at 5,6,7pm… if you’re employed – which is another issue.

        • SplitFingeredPujol 4 years ago

          Yeah, I honestly do feel for the fans that are there. The fact that it isn’t fashionable to be a Rays fan basically verifies their passion for the team. So to the few Rays fans reading this, I say this with empathy. But your team NEEDS to leave. It’s inevitable. It’s necessary.

  2. SplitFingeredPujol 4 years ago

    I think Votto makes the most sense of any of these guys, based on skill set, age, organization, and present contract.

    • I feel the same way but unfortunately Votto doesn’t. He said he couldn’t imagine signing a deal like Tulo’s when it happened. As he put it he couldn’t see how signing your next ten years away is worth the security. I think he values winning over anything and a long term contract could put him in a situation where if the team falters then he is stuck for a long time. Apparently he wouldn’t be happy with $100+ mil if he was losing. Commendable but as a Reds fan I wish he would have given us some FA years rather than just signing for his 3 arb years.

  3. David Anderson 4 years ago

    Why the hell aren’t Ethier and Kemp on this list?

    • SplitFingeredPujol 4 years ago

      If you didn’t notice, each player mentioned had already signed decent extensions. Also, do you realistically think the Dodgers of all teams are in a financial situation to take on such risk? In the future, sure. But not now. Not a chance.

    • Because Ethier is already 29 so if he is to be locked up until 2020 he’d be a Dodger until he 39 and Matt Kemp who is going to turn 27 this year and that would put him at 36 at the end of his contract. Most teams don’t want to sign players for that long unless they are 25 or under. Plus aren’t Ethier and Kemp both really close to being free agents? So they are less likely to get extensions due to the temptation of free agency.

      • lakersdodgersyankees4life 4 years ago

        They both will be FA after next year. To splitfinger, they both signed extensions during their arbitration years to set their salaries. Kemp has the tools to play at a high level until his mid to late 30s, a true 5 tool player, and Andre has a bat that has only gotten better with age thus far.

        With MLB taking over the Dodgers, it would seem like a good time to try to secure one of these guys to a long term deal to try to add some stability to the team.

        • SplitFingeredPujol 4 years ago

          I think the idea though is that the guys listed already had pretty substantial extensions in place going beyond their post-arb years. That’s the type of extension they’re talking about. Neither Kemp nor Ethier fits that contractual description. I’m not doubting the talents of either player (maybe Ethier, but Kemp is a beast). And as for the Dodgers financial situation, I don’t think there has been any situation in which MLB has been in control on a teams finances and made this kind of financial risk/commitment, is there? Sincere question. I doubt it thought.

          • lakersdodgersyankees4life 4 years ago

            Andre is a LF who is playing RF out of need. In LF, I do think he’d be a more well rounded player. As for the other part, I honestly don’t know because I only know of two times MLB has done this. Maybe it would happen if they had a sale nearly in place so the MLB wouldn’t be making a franchise altering move. However, the point is both of these guys have a very strong case to deserving a long term deal and would probably have one already if on a different team
            Sent on the Sprint® Now Network from my BlackBerry®

      • theophilus166 4 years ago

        Cano is 28, Hanley is 27, and Cabrera is 27, so they’re in the same age range as the other guys on this list.

        • But they are also better than the above. There is less of a risk with signing those players long term than Kemp and Ethier in my opinion. I think Kemp still has to prove that he can be consistent before he deserves a mega deal.

  4. Devern Hansack 4 years ago

    You forgot Jayson Werth.

  5. Notin J. Notin 4 years ago

    Mike Aviles

  6. iorekk 4 years ago

    what about vernon?

    • SplitFingeredPujol 4 years ago

      But if he signs an extension he’ll lose his apparently considerable trade value?

  7. JacksTigers 4 years ago

    I know he has had some off the field problems, but Miguel Cabrera has shown he can hit no matter what’s going on. I would hate to lose him therefore I think we need to extend him.

    • SplitFingeredPujol 4 years ago

      I’m not doubting his ability to hit the ball. It’s elite. But….that body type tends to catch up with guys. He’s the last guy listed I’d give that kind of extension to.

      My favourite player growing up was the Big Hurt. Thomas was a better hitter, but comparable. But his body couldn’t hold up beneath him, and he didn’t have any of the off-field questions that Cabrera has. Cabrera is like a Frank Thomas body with Andruw Jones’ attention to physical fitness.

      • JacksTigers 4 years ago

        Barry Bonds body held up pretty well until the roids got to him. Albert Pujols also has a similar body type.

        • 0bsessions 4 years ago

          Barry Bonds’ body held up well BECAUSE of the roids. Given, roids eventually catch up to you, but a big part of the point of steroids is to accelerate healing in a relatively superficial way. If you heal faster, the muscle tears you generate heal quicker, allowing you to work out more.

      • alphabet_soup5 4 years ago

        Idk why everyone thinks Cabrera is a fat-ass….he’s not skinny by any means but he’s slimmed down since Florida.

  8. mdv1959 4 years ago

    I’d lock up Jared Weaver ASAP. Kendrys Morales wouldn’t be a bad guy to extend too.

    • JacksTigers 4 years ago

      I’d think twice about giving an extension to a guy who is capable of breaking his leg and being out for nearly a year when celebrating a walk off homerun. I’m not sure of how durable he actually is and I’d hate to pay a guy that much to watch him pull a Griffey.

  9. yazpik 4 years ago

    Vernon Wells 100 millions 5 years at the end of his actual contract makes sense…

  10. Brian McCann?

  11. Lunchbox45 4 years ago


    He’s only locked up til 2020, Brewers should extend him.

  12. as a marlins fan, I’d rather get jj locked up throgh 2020 than hanley.

    • Lunchbox45 4 years ago

      locking up pitchers to long term contracts is always a good idea

      • have you seen him pitch? all im saying is that I’d rather them spend money on a guy who looks like he could be the second coming than on a guy who already got his extension and hasn’t played the same since. Hanley also is a terrible clubhouse guy and doesnt work hard on the field. My dream is to go back in time 5 years and sign miguel cabrera to a thousand year extension

        • Lunchbox45 4 years ago

          I’ve seen JJ pitch

          JJ is freaking awesome

          but you know when he wasn’t awesome? 2007-2008 when he was injured..

          • JacksTigers 4 years ago

            Do you know who else was awesome? Barry Zito.

          • 0bsessions 4 years ago


          • JacksTigers 4 years ago

            When he was with Oakland. Why else would you think that he got a 100MM+ contract? He used to be a premier pitcher.

          • 0bsessions 4 years ago

            He got a $100MM+ contract due to the ineptitude of the Giants front office at the time. Zito has ALWAYS been a junk baller who had the benefit of a solid defense behind him in Oakland. Zito was “good” in Oakland, but never particularly outstanding or awesome.

            Barry Zito was basically Daisuke Matsuzaka with better luck. Zito got that contract due to awful due dilligence on the part of the Giants and it is, to date, probably the worst contract in MLB history.

          • East Coast Bias 4 years ago

            That reminds me, Dice-K should be on this list!

  13. LinkinParkFTW 4 years ago

    First person I thought of was Pedroia. (Yes, I’m a Red Sox fan.) It just seems like every time I see him play he does something special. I want him to stay in Boston for a long time.

    • 0bsessions 4 years ago

      If his performance continually justifies it, he’ll be around. Like Cano, the Red Sox have little reason to extend Pedroia now. If they extended him, they’d have to concede to a higher current salary to get any extra time. As it stands, the only team who could afford to give him more money than us is likely to continue employing Robinson Cano. We could be looking at another Jeter/Garciaparra situation here (Hopefully minus the eventual injury problems as my heart can’t take that).

  14. safari_punch 4 years ago

    There was clearly an oversight with this article.

    Why no Derek Jeter?

  15. Michael Brown 4 years ago

    What about McCann, Heyward, Hanson?

    • 0bsessions 4 years ago

      Not if you actually read and understood the introduction to the article.

      • Michael Brown 4 years ago

        Sorry I was unaware that J-Hey is not a franchise player.

        • 0bsessions 4 years ago

          Dude, come on! I call you on it and you STILL don’t go back and read it?!

          “Should other clubs look to explore this tactic of extending an extension, here are some of the possible candidates to join Braun and Tulowitzki in the “2020” club.”

          Did Heyward sign an extension while I wasn’t looking or something?

          • Michael Brown 4 years ago

            Eh, it was early…You win.

          • 0bsessions 4 years ago

            Woooooo! Take THAT, internet!

          • heyward did not, but mccann did and his runs out at the end of the 13 season…i wouldnt mind tacking on an addition 4 years onto that deal

          • 0bsessions 4 years ago

            The post was edited (And don’t ask me why it’s not reflected, Disqus stinks), originally he’d said something along the lines of it being a grave injustic that Heyward was overlooked for this article.

          • Michael Brown 4 years ago

            Other than the Discus sucks argument, which is very true. Maybe it’s because I edited it within 30 secs of posting it. Again it was early…I failed to read the article.

          • Extending catchers for long durations is almost always a bad idea. While I know alot of people loved the move, I thought at the time that Mauer’s contract by the end could outpace the wells/soriano/zito deals as potentially the worst signing in history. The twins would never admit it, but you have to wonder if they’ve questioned their signing seeing as 1 year into a $180mill deal people have already started to wonder about whether he should be moved. .320/8hrs is great from a catcher, but from a 1st/DH, you’re pissing millions and millions of dollars away.

            Anyways I digress, extending catchers, even quality ones that are still fairly young for seriously long durations just screams huge risk.

  16. LUWahooNatFan 4 years ago

    Rizzo- Sign Zimmerman, now.

  17. AmericanMovieFan 4 years ago

    My serious (and totally biased) vote as a Yankee fan is Robinson Cano. He’s already making 8-figures this year, he’s already got a pretty hefty $2MM buy out on a $14MM option that is all but guaranteed to be picked up and he just hired Scott Boras. Do the math. He’s remained healthy and consistent and has only improved as time has gone on. Time to get this done. It doesn’t need to break records, just need to be fair.

    I say either throw out his current options and give him 7 years/$119MM or make his two options guaranteed, then extend him for 5 years/$90MM. The only potential obstacle I see to this is Jayson Werth’s contract. Cano is a better, younger player at a more prime position than Werth and he’s got Boras repping him.

    In a worst case scenario, I could see Boras convincing him to go for broke and ask for something like 10 years/$200MM.

    • JackParkman 4 years ago

      I agree, Robbie Cano is gonna get paid, BIG TIMe

      • 0bsessions 4 years ago

        Given, but almost certainly not until he hits free agency. All doing it before that would accomplish is MAYBE saving the Yankees a couple bucks and I really don’t think they much care about that possibility.

        Heck, I could honestly see waiting until free agency and then making a big deal about it in the offseason generating a lot more revenue in terms of ticket sales than signing an extension now when no one really cares. Now that’s something I’d like to see concrete research on.

  18. 0bsessions 4 years ago

    I just don’t see the Yankees offering him an extension while he’s still under contract for so much longer. It just doesn’t seem to be their general M.O.

    While Cano isn’t exactly the least sensible candidate up there, I’d call him least likely considering who he’s already signed with. Sure, the Yankees aren’t shy about throwing buckets of money at a guy, but what incentive do they have to extend him now?

    Teams like the Rockies and Brewers offer these mega extensions to avoid the potential of their free agents getting scooped up by the Red Sox and Yankees.

    A player will snub big money for one reason and one reason only: there’s another team he’d rather play for. Cano is already firmly entrenched as a Yankee and no one’s going to offer him more money than them. Unless he absolutely hates it there, he’s pretty much going to sign another long term deal when his current deal is up. Even more likely now that the Yankees are starting to actually develop some talent, which would free up a lot of room to overpay him if necessary.

    While yes, Cano looks to be the real deal and they COULD save money by extending him now and it would be in Cano’s best interest to do so (Long term security, a big fat paycheck), the Yankees have no real compelling reason to extend him right now considering their means.

  19. TapDancingTeddy 4 years ago

    Cashman will wait Cano out and pay him market when he reaches free agency. Hanley Ramirez is likely to end up with another team, The Rays are short resources to do much more with Longoria.

    There are a lot of problems with those potential extensions. But, if I were the Nationals GM, I’d want as much Ryan Zimmerman as I could get. Zimmerman is their signature player and he is still very young.

    • 0bsessions 4 years ago

      I think Zimmerman makes the most sense to me. The Nationals have the money to afford it and the future pieces to justify keeping him around, but bigger markets will be frothing at the mouth for him if he hits free agency. Kevin Youkilis’s contract ends concurrently with Zimmerman’s (And if I noticed that coincidence, Epstein noticed it a lot sooner) and the Yankees are going to have to move A-Rod to DH full time sooner rather than later. The last thing the Nationals need is for one of their best position players becoming the object of a Sox/Yankees bidding war.

      • TapDancingTeddy 4 years ago

        Excellent point about him becoming a Sox-Yanks target the year he hits the market. A lot could happen between then and now, but it would not be pretty watching the Nats try to keep Zimmerman from the two biggest wallets in baseball.

  20. alphabet_soup5 4 years ago

    I think that Detroit should extend Cabrera. If he can hit like this with “off-field problems”, then imagine what he could hit like if he didn’t have any. He should be a serviceable first basemen for many more years and is arguably the best right handed hitter in the American League.

  21. notsureifsrs 4 years ago

    when he pries it from josh beckett’s cold dead fingers

  22. Ian_Smell 4 years ago

    Bruce Chen is the coolest person in baseball. If I could, I would absolutely give him a Cy Young vote.

  23. notsureifsrs 4 years ago

    literally 2 minutes later that happened. apparently even jokes can have a terrible jinxing effect

  24. SplitFingeredPujol 4 years ago

    It has to be. I like it.

  25. yazpik 4 years ago

    He´s a prospect, don´t rush him…

  26. Lunchbox45 4 years ago

    press shift + control

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