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    Which Young Twins Should Get an Extension This Winter?

    Jeremy Zoll says Minnesota will explore extensions. Here are six young players who could make sense for an early commitment.

    Cody Christie
    Image courtesy of Kiyoshi Mio - IMAGN IMAGES via Reuters Connect

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    Major League Baseball has increasingly become a league where teams are willing to bet on young players before the players have had much opportunity to cash in on their potential.

    That trend has accelerated in recent years. Teams have handed out long-term contracts to players with very little service time, and some have even made commitments before a player reaches the majors. In 2026 alone, Colt Emerson, Cooper Pratt and Luis Lara signed extensions before making their MLB debuts, while several other highly regarded young players received significant guarantees almost immediately after reaching the majors.

    The strategy is relatively simple. A team gives a young player financial security early, while potentially buying out arbitration seasons and some free-agent years at a lower cost than the player might command after establishing himself as a star.

    The Minnesota Twins have watched that trend from the outside. This winter, they could finally decide to participate. General manager Jeremy Zoll said the organization plans to explore contract extensions with some of its young players during the offseason. Zoll also explained why he prefers to have those discussions away from the regular season.

    “As it pertains to extension conversations, that’s definitely something we’re going to explore this offseason and going forward,” said Zoll. “I know there have been in-season extensions around the league. Personally, I don’t think it serves anyone particularly well to potentially create a distraction for players during the season on those fronts. So those will be things we’ll engage in this offseason and we’ll see how that all shakes out.”

    That leaves a fascinating question for the Twins. Who exactly should they be talking to?

    The Twins Have Seen Both Sides of This Equation

    There is an obvious appeal to getting ahead of the market. If a player becomes a star, the price is going to increase dramatically. If the Twins can identify that player early enough, they could potentially secure several years of production at a manageable cost.

    But the organization also has plenty of evidence for why patience can be valuable. As explored earlier this year, the Twins had opportunities to make long-term commitments to players such as Royce Lewis, Jose Miranda and Matt Wallner when their perceived values were significantly higher.

    Lewis looked like an obvious extension candidate following his spectacular 2023 campaign. He hit .309/.372/.548 with 15 home runs and a 149 OPS+ in 58 games before starring in the postseason. Today, Lewis is coming off a disappointing 2026 season in which he hit .227/.287/.380 with a 86 OPS+ and 0.9 WAR.

    Miranda provides another cautionary tale. After posting a 114 OPS+ as a rookie in 2022, his production collapsed in 2023 (55 OPS+) before rebounding in 2024 (112 OPS+). There were flashes of his strong bat-to-ball skills, but he never put it all together at the big-league level. He was eventually out of the organization and played the entire season in the minors this year. 

    Wallner provides another example of the uncertainty surrounding young players. His power looked like something the Twins could build around, but injuries and strikeouts have prevented him from establishing himself as a consistent everyday player. In 2026, he hit just .167/.259/.292 with a 55 OPS+ in 34 games before being demoted to Triple-A for the remainder of the season. 

    The lesson isn't that extensions are bad. It is that the Twins need to be extremely selective about which players receive them. That brings us to this winter's potential candidates.

    Taj Bradley

    The case for an extension: Bradley might have the strongest argument among Minnesota's young pitchers. The 25-year-old right-hander made 31 starts and threw 178 1/3 innings in 2026, posting a 3.73 ERA, 3.82 FIP and 205 strikeouts. He produced 4.4 WAR while becoming one of the most important pieces of Minnesota's rotation. There is also a reason to believe the best is still ahead as he is only 25-years old. Bradley has already demonstrated the ability to miss bats while carrying a starter's workload, and he has three years remaining before free agency.

    The case against an extension: Pitching is inherently risky, particularly when discussing a multi-year commitment. Bradley has only one season at this level of workload and production. His 1.22 WHIP and 76 walks also show there is still room for improvement. The Twins would be buying into both his 2026 breakout and the expectation that he can sustain it.

    Luke Keaschall

    The case for an extension: Keaschall looks like exactly the type of player teams target with early extensions because he is under team control through 2031. At 23, he followed his impressive 2025 debut with a full 2026 season in which he hit .282/.374/.407 with 10 home runs, 20 stolen bases and 2.2 WAR. His 120 OPS+ shows his offensive production was comfortably above league average.  More importantly, Keaschall's game isn't dependent on one tool. He provides on-base ability, speed while still having room to develop more power. The Twins can plug him into the top of the lineup for the foreseeable future. 

    The case against an extension: His power profile is still somewhat uncertain. Ten home runs in 620 plate appearances isn't overwhelming, and his .407 slugging percentage leaves some questions about his long-term offensive upside. His defensive metrics also weren't particularly strong across his various positions in 2026. An extension would be betting that Keaschall's overall offensive profile continues to develop.

    Walker Jenkins

    The case for an extension: Jenkins may have the highest offensive ceiling of anyone on this list. The fifth overall pick in 2023 entered 2026 as one of baseball's top prospects and ultimately reached the majors at age 21. Before his promotion, Jenkins produced a .323/.417/.559 line with 14 home runs, 17 stolen bases and a 151 wRC+ across 73 minor-league games.

    His major-league debut was much more modest, as he hit .226/.293/.393 with a 91 OPS+ in 93 plate appearances. But that small sample doesn't erase the larger body of work. Jenkins remains one of the organization's most intriguing long-term building blocks.

    The case against an extension: This is precisely where the Lewis lesson comes into play. Jenkins has barely begun his major-league career. The Twins would be committing significant money based primarily on prospect pedigree and minor-league performance rather than established MLB production.

    There is also the Scott Boras factor. Jenkins' representation could make an early deal more difficult to negotiate, particularly if the player believes his eventual earning power could be enormous.

    Connor Prielipp

    The case for an extension: Prielipp's underlying numbers provide more optimism than his ERA. The left-hander finished 2026 with a 4.87 ERA but a 3.73 FIP over 125 2/3 innings. He struck out 128 hitters while allowing only 14 home runs. Considering his lengthy injury history, simply completing a full season while establishing himself as a major-league starter represents an important step forward. If the Twins believe his FIP is more representative of his future performance, there could be an opportunity to buy low before his results catch up with his underlying skills.

    The case against an extension: This is a much larger projection than Bradley. Prielipp still hasn't demonstrated sustained major-league success, and his 1.29 WHIP and 4.87 ERA leave plenty of uncertainty. He also has a history of significant injuries, which makes a long-term pitching commitment particularly complicated. There is a reasonable argument for simply letting Prielipp prove more before committing.

    Kaelen Culpepper

    The case for an extension: Culpepper's 2026 season provided two encouraging data points. First, he dominated Triple-A, hitting .271/.367/.478 with 14 home runs and 17 stolen bases in 74 games. Then he reached Minnesota and held his own, hitting .274/.328/.393 with a 102 OPS+ over 33 games. The combination of shortstop defense, athleticism and offensive upside makes Culpepper an intriguing long-term piece.

    The case against an extension: He has only 128 major-league plate appearances. That's not enough information to know whether his offensive production will translate over a full season. His 28 strikeouts against just six walks in 128 plate appearances also highlight areas that need improvement. Culpepper may be a player the Twins should monitor closely rather than rush to sign.

    Emmanuel Rodriguez

    The case for an extension: Rodriguez remains one of the organization's highest-upside offensive players. He reached the majors in September after another productive minor-league season (140 wRC+) and made his debut at 23. His combination of power, plate discipline and athleticism has made him one of the more intriguing prospects in the system for several years. The Twins would be buying before Rodriguez has had a chance to establish himself as a major-league hitter. That's exactly what makes an early extension potentially valuable.

    The case against an extension: There simply isn't enough MLB evidence yet. Rodriguez went 8-for-45 with two home runs and a .178/.229/.400 line during his brief major-league debut. That obviously isn't enough to make a judgment about his future, but it demonstrates how much uncertainty remains. There are also questions about whether his long-term defensive home will maximize his value. The offensive upside is exciting, but the Twins would be paying for potential.

    Where Should the Twins Start?

    There is no reason for Minnesota to hand out extensions simply because other teams are doing it. The purpose of an early extension is to identify a player before the market catches up and create cost certainty before arbitration and free agency become expensive. But the Lewis, Wallner, and Miranda examples demonstrate how quickly that calculation can change.

    Bradley has the strongest major-league track record of this group. Keaschall has the largest body of MLB work among the position players. Jenkins has perhaps the greatest long-term ceiling. Prielipp represents an intriguing buy-low opportunity, while Culpepper and Rodriguez remain higher-risk bets on potential.

    The Twins don't need to pick just one. But they also don't need to force the issue with all six. Zoll has made it clear that extensions will be part of the offseason conversation. Now the difficult part begins: deciding which young players have shown enough to justify turning potential future value into guaranteed money today.

    For a franchise trying to build its next competitive window, those decisions could be among the most important of the winter.


    What player or players should the Twins approach for contract extensions this winter? Leave a comment and start the discussion.

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    30 minutes ago, killercarewoliva said:

    guys are making $70 million a year

    There's not a single player in MLB making $70 million a year. Not even a single player making $60 million a year. So you're not even sure what you're mad about. 

    But you know who makes significantly more than that? The owners. But they deserve it, as we all know. 

    7 minutes ago, MackMan said:

    IDK. This dude is beyond me. If owners really wanted to make more money they would cut salaries and just put out a HS team where these kids would be happy to make $100k/year to lose and play baseball. Now the players union and league would have to step in and prevent this from happening because that would be a stain on baseball. 

    I tried mentioning to this guy yesterday that the way to get fans into the park is field a competitive team. A good team will cause fans to come to the game, which in turn the ownership team can raise the prices to tickets to what is needed to get people into the game. But on the other hand if a team is horrible, the ownership needs to cut ticket prices to get people in and hope those fans are going to buy from the merchandise and food. I would rather have a full stadium at 1/2 price tickets than a 1/2 full stadium from full priced tickets. The money is the same, but if people only pay $20/ticket versus $50-60/ticket, they may be more apt to spend on food and merchandise. 

    I appreciate your feelings, but I do think your nostalgia is blocking out a few points:
    - MLB is not a sport, none of pro sports are. MLB is entertainment disguised as a sport. If you want true competitive sports, stick with high school, low college, or (mostly) the olympics.
    - Owners and players are not in this for the love, they are in it to make money. MLB players may love to play, but they do it professionally to get paid. Talk to enough pro athletes and you will learn that pretty quick.
    - Owners will charge whatever ticket price the market will allow. Any promotion they run is done to ultimately bring more fans to games and make more money. Period.

    19 minutes ago, MackMan said:

    IDK. This dude is beyond me. If owners really wanted to make more money they would cut salaries and just put out a HS team where these kids would be happy to make $100k/year to lose and play baseball. Now the players union and league would have to step in and prevent this from happening because that would be a stain on baseball. 

    I tried mentioning to this guy yesterday that the way to get fans into the park is field a competitive team. A good team will cause fans to come to the game, which in turn the ownership team can raise the prices to tickets to what is needed to get people into the game. But on the other hand if a team is horrible, the ownership needs to cut ticket prices to get people in and hope those fans are going to buy from the merchandise and food. I would rather have a full stadium at 1/2 price tickets than a 1/2 full stadium from full priced tickets. The money is the same, but if people only pay $20/ticket versus $50-60/ticket, they may be more apt to spend on food and merchandise. 

    Attendance has more than doubled since the ""glory days" of players being paid like high school principals, even though ticket prices were so much cheaper.  The explosion of TV broadcasts bringing more eyeballs to the product (showing a game on TV is a great advertisement for getting people to want to experience what they're seeing in person) drove up the demand, and by extension the price, of tickets.   All this additional revenue from both TV and tickets, with the combination of free agency, resulted in the increase in player salaries.  Revenues dictate player salaries, not the other way around. 

    Anyone rooting for the players to make less money is rooting for the owners to make more money.  Your ticket prices won't get touched in the process.

     

    Just now, Twins GFP said:

    I appreciate your feelings, but I do think your nostalgia is blocking out a few points:
    - MLB is not a sport, none of pro sports are. MLB is entertainment disguised as a sport. If you want true competitive sports, stick with high school, low college, or (mostly) the olympics.
    - Owners and players are not in this for the love, they are in it to make money. MLB players may love to play, but they do it professionally to get paid. Talk to enough pro athletes and you will learn that pretty quick.
    - Owners will charge whatever ticket price the market will allow. Any promotion they run is done to ultimately bring more fans to games and make more money. Period.

    You have literally agreed to all my points. Everything is viewed from a business perspective. It has to be. Player make what they make because the market says so. The ownership charges what they charge for tickets because the market says so. The objective of the game is make a much money as possible with spending as little as possible. Now for a team like the Twins, the Pohlads have done that to a degree. And now their lack of spending or fielding a competitive team is coming round to bite them with their lowest attendance in the 17 season since Target Field opened.

    Ownership cried and complained that they needed a new ballpark to stay competitive in the baseball market. They have had 5 playoff appearances since 2010, 1 series win, and an otherwise poor showing. But that's the thing about baseball. Because there isn't a cap or a floor, teams are always spending differently based on market size. Not every team that spend $250+ million makes the playoffs (Mets), but not every team that spends less than $80 million (Rays, Cleveland) also makes the playoffs. Some teams buy their talent whereas others have to rely on homegrown talent before those players hit the open market. Baseball really has the most disparity amongst NA professional sports. 

    1 hour ago, killercarewoliva said:

     

    can't any older people respond because the choice is ludicrous. I'm not going to pay $50 for a loaf of bread. that choice does not need to be there. it's called scanning the public.

    I'm not as old as Chief (who may be lurking), but I can remember when bread was 50 cents, and a Twins ticket was $5 for a good box seats at the Met.   But those days are gone.  (And a baseball ticket that cost $5 in the mid 1970s would be $30+ today adjusted for inflation)

    Teams are going to charge what the market will bear... always, and regardless of player salaries.  That's just capitalism.  Big time college football and basketball tickets have long been equally expensive, and until recently those players weren't even being paid.

    I don't even think the owners care particularly if the stadium is full.  They just want to maximize revenue, and if that means the good seats go for hundreds of dollars per game instead of dozens of dollars, that's what they will charge, even if a few remain unsold.

    You can argue it's a scam, but it is more a matter of everyone but the wealthy being priced out.  The 1% doesn't worry much about paying $500 or more for a seat... it is pocket change for them, and the franchise owners are more than happy to empty their pockets. 

     

    For the right price, you can extend anybody, but the only one of these guys I'd want to give meaningful money to is Jenkins.

    Keaschall is fun, but he's already under team control for his prime-age seasons, he's limited to corner outfield, and he doesn't have the power to be a true star at the position. He can be good, but he's unlikely to be a "must-have" guy in his free agency years.

    Rodriguez is fun to dream on, but he's never played a fully healthy season, the contact skills are alarming, and he's going to end up in a corner spot. That's fine, but once again, I don't think he's someone you absolutely want around seven years from now, in his 30s. A good career outcome for him is the next Joey Gallo. 

    Culpepper is a nice story, and he's already become much more intriguing than I expected when they drafted him. But he's probably not a long-term shortstop, and while I think he can be a good player as a second or third baseman, the offensive profile is less impressive once he moves off short. Like the others, he absolutely has the potential to be good, and it's fair to be excited about him, but I don't see any reason to commit to him as the third baseman of the future more than half a decade out.

    Down in the minors, it seems like Houston is probably a legit shortstop, but he's already under team control for the years you'd want from a glove-first middle infielder. I guess if you were extremely confident, you could extend Lackey, but that would be an extremely aggressive move given how catchers age.

    On the pitching side, I know people have fallen in love with Taj, but he's an extreme fly-ball pitcher who relies heavily on fastball velocity. That's fine, and it can lead to good results, but it's not a skill set that usually ages particularly well.

    Prielipp was a fun story and does have the upside of a playoff-caliber starter, but he's already under team control through age 30 and has enormous injury questions. If he's in the org through the end of arbitration, that's probably a win, so I don't know why you'd want to add years.

    A bunch of these guys are exciting, but so much of their collective prime age seasons are already team controlled.

    16 minutes ago, Andy MacPhail said:

    MIL offer their promising young players extensions because they are confident that they can bring them to their potential. Twins can't do that, They aren't confident, it's more based on luck. They can offer Bradley & maybe Keaschal.

    I think I'd actually do Culpepper ahead of either of these two.  Keaschal *might* be a better hitter, but Culpepper clearly has a better glove that will play somewhere, even if his bat doesn't develop fully.

    Nothing against Bradley...just that injuries are such a high risk for every pitcher.

    54 minutes ago, killercarewoliva said:

    I can sit behind home plate for $4.50 that was 1967 in 1992. I could sit behind home plate for $12.50 the next year. it went up to $15. that's in Baltimore. I want to see the game. I don't want to have to pay $1,000 to see the game. you can't see the game when you're paying $10. not like I want to see it. I will not be cheated at a sporting event or at a music event. if the price is way too high I want to see whoever play I'm not going. I'm not going to give in to their cheating money style. I have a 70-in big screen TV and I will watch the games there. I often think in New York $1,600 to sit behind the Yankees dugout that was 10 years ago. you can't see the game from there because you need to sit behind home plate where you can see the movement of the baseball, what it's doing. then you can gauge how good a time at bat or not the batter had. he don't know that sitting anywhere else. I love baseball. there's nothing like him and that's on and off the field. you can't truthfully judge a player's ability drafting him out of high school or college like you can in other sports. I'm a true Vikings fan. their offense is in the tank and I think they made a mistake with the new quarterback. I choose to see the game where I can see the game and that's been taken away a long time ago. I sat on the third row behind home plate to see Johan Santana pitch for $75 and that's the most I've ever paid to see a ball game. how much does that cost now hasn't been that long ago. it's crazy and the fans just keep right on paying for it. guys are making $70 million a year. $100 million is going to come. where is the money going to come from? how many people are going to want to pay that much of their hard-earned bucks to see that guy? if that guy has to have that much money and they want to steal money like that from us, screw them I'm not going to root for them. I've taken my Minnesota twins license plate and throwing it in the trash tree because I don't want to promote money making deals like that. nothing against the players really. they take what they give them but I can't root for that kind of income. so the license plates are gone. I'd like all of baseball to know what I'm trying to say. also, in Baltimore there's one entrance you can bring in your own food.

    Nice rant.  A little incoherent at times but everyone understands your position.  The only thing you left out was:  Hey!  You kids get off my lawn!

    I think the article would've benefitted from mentioning the uniqueness of this offseason (lockout / new CBA) as potential factors in the extension equation.

    1) Will the unknowns of the lockout motivate young players to sign an extension that includes a signing bonus? For Example: Taj Bradley. Taj got a 750k signing bonus in 2018 and has been paid roughly 800k per season the last three years. That's nothing to sneeze at, but it's not "change your life" money yet, he probably doesn't have a TON of savings based on what he's earned so far, and he plays a very injury prone position. The flip side of that is Walker Jenkins. He got $7.1M just 3 years ago. Sure he's further from free agency, but he got that big signing bonus and he plays a less injury plagued position. I'm not saying he doesn't have ANY motivation to sign a big extension, but probably less motivation than Taj. Taj getting a $5M signing bonus as part of an extension, probably sounds pretty good heading into the unknown of the offseason and 2027.

    2) Will a potential change in CBA related to service time and arbitration demotivate players from wanting to sign an extension? You can also flip that around and say, if the clubs think the new CBA will reduce the service time clock from 6 to 5 years, do the teams have MORE motivation than normal to get young players locked up for a year or two past their current free agency year? As a team, I'd rather be negotiating an extension under the current setup compared to what a new setup might be. It's might not change at all, but the service time clock certainly isn't getting LONGER than it is now. 

    Why would you ever extend a young pitcher?  I mean there might be cases where you guarantee salary to get a team option on the first free agent year.

    Culpepper showed a little, may not be good.  Probably a player but not a star.

    Taj is being considered here with no mention of his arbitration/free agency status?  He's in his first year of three arbitration years.  Usually at this point with pitchers, only misguided extensions will be considered by their agents.

    Jenkins is represented by Boras.  There will not be an extension unless the Twins overpay by a lot.  That said, it might not be a bad idea.  He'll be better than any other player on the team.

    Prielipp is an injured pitcher.  As Pablo says, you get only about 5-6  from TJS until it's going to be needed again.

    Keaschall is a nice players without a proper defensive spot to take advantage of the type of hitter he is.  Yeah, extend him.

    Lewis was never an obvious extension candidate, not that it mattered with Boras.  He certainly wasn't the type you'd overpay, like Jenkins may well be.

    EmRod isn't worth anything.  I'd guess he won't be hanging in the majors by the time his free agency years kick in.  Even the Twins are smart enough to have traded him if some team valued him as somebody who they would extend.

    Miranda and Wallner weren't candidates.  What's your criterion, that Twins Daily overrated them?

    I would engage Boras on Jenkins, let him set his price, and match it or move on.  99% that means moving on.  Keaschall is probably cheaper and worth extending.

     

     

    4 minutes ago, Whammy said:

    I think the article would've benefitted from mentioning the uniqueness of this offseason (lockout / new CBA) as potential factors in the extension equation.

    1) Will the unknowns of the lockout motivate young players to sign an extension that includes a signing bonus? For Example: Taj Bradley. Taj got a 750k signing bonus in 2018 and has been paid roughly 800k per season the last three years. That's nothing to sneeze at, but it's not "change your life" money yet, he probably doesn't have a TON of savings based on what he's earned so far, and he plays a very injury prone position. The flip side of that is Walker Jenkins. He got $7.1M just 3 years ago. Sure he's further from free agency, but he got that big signing bonus and he plays a less injury plagued position. I'm not saying he doesn't have ANY motivation to sign a big extension, but probably less motivation than Taj. Taj getting a $5M signing bonus as part of an extension, probably sounds pretty good heading into the unknown of the offseason and 2027.

    2) Will a potential change in CBA related to service time and arbitration demotivate players from wanting to sign an extension? You can also flip that around and say, if the clubs think the new CBA will reduce the service time clock from 6 to 5 years, do the teams have MORE motivation than normal to get young players locked up for a year or two past their current free agency year? As a team, I'd rather be negotiating and extension under the current setup compared to what a new setup might be. It's might not change at all, but the service time clock certainly isn't getting LONGER than it is now. 

    I completely agree with you. If the FO of teams want to lockup these younger teams, they need to do it now more than ever. Because I feel as if the new CBA is going to target FA and MLB service time the most. Players want to be able to test the markets before their Prime is done. 

    I know it doesn't happen to every player, but spending 11+ seasons with an organization and then reaching FA in your early to mid 30's can really take a toll on someone mentally. Especially if they were with a team they didn't want to be with or a team that refused to put a winning product on the field. 

    Personally I think believe that there should almost be incentive based. For example currently you need 6 yrs of MLB service to be eligible for FA. I think that if you win an MVP/CY Young within the first 5 years of your team control, you should be eligible after season 5 for FA. Incentivize owners trying to lock up players at a younger age to keep their teams competitive. 

    1 hour ago, MackMan said:

    You have literally agreed to all my points. Everything is viewed from a business perspective. It has to be. Player make what they make because the market says so. The ownership charges what they charge for tickets because the market says so. The objective of the game is make a much money as possible with spending as little as possible. Now for a team like the Twins, the Pohlads have done that to a degree. And now their lack of spending or fielding a competitive team is coming round to bite them with their lowest attendance in the 17 season since Target Field opened.

    Ownership cried and complained that they needed a new ballpark to stay competitive in the baseball market. They have had 5 playoff appearances since 2010, 1 series win, and an otherwise poor showing. But that's the thing about baseball. Because there isn't a cap or a floor, teams are always spending differently based on market size. Not every team that spend $250+ million makes the playoffs (Mets), but not every team that spends less than $80 million (Rays, Cleveland) also makes the playoffs. Some teams buy their talent whereas others have to rely on homegrown talent before those players hit the open market. Baseball really has the most disparity amongst NA professional sports. 

    I attached the wrong post on the thread. Me and you giphy.gif

    2 minutes ago, Linus said:

    Ya know, ignoring someone is almost always a better choice than making a derogatory, personal comment. 

    You're absolutely right in that it is. But I am just petty enough to where I cannot let things like that stand. It is my hill to die and I will defend it. 

    I think it's important to acknowledge why each side might be considering a "pre-free agency" extension. I feel like most analysis of extensions ignores several of the motivations.

    Player motivations:
    1) Up front money. Via either a signing bonus or higher annual salaries when they might be otherwise making the league minimum
    2) Guaranteed money, which can mitigate poor future performance or can be injury insurance.

    Team motivations:
    1) Cost certainty. It's easier to create a long term plan if you know how much money players on your roster are going to cost 3, 4, 5 years from now.
    2) Long term money savings. Teams pay more early in the contract with the idea that what would be arbitration years, or free agent years don't cost as much
    3) Additional years of team control. Having a player guaranteed to be on your team beyond the 6+ years of team control that the current CBA allows for.

    I know some of those sound obvious to say out loud, but they almost all play a part, and some of them often get ignored.

    9 minutes ago, Whammy said:

    I think it's important to acknowledge why each side might be considering a "pre-free agency" extension. I feel like most analysis of extensions ignores several of the motivations.

    Player motivations:
    1) Up front money. Via either a signing bonus or higher annual salaries when they might be otherwise making the league minimum
    2) Guaranteed money, which can mitigate poor future performance or can be injury insurance.

    Team motivations:
    1) Cost certainty. It's easier to create a long term plan if you know how much money players on your roster are going to cost 3, 4, 5 years from now.
    2) Long term money savings. Teams pay more early in the contract with the idea that what would be arbitration years, or free agent years don't cost as much
    3) Additional years of team control. Having a player guaranteed to be on your team beyond the 6+ years of team control that the current CBA allows for.

    I know some of those sound obvious to say out loud, but they almost all play a part, and some of them often get ignored.

    This is absolutely correct. Players want their money for their current/future performances. They don't want to hit just to get paid. Whereas fans and owners want to look at the WAR vs money spent deal. If a team can get a team-friendly deal that is similar to Buxtons, but can get close to 6-8 WAR out of a single season, that was worth the price.

    The real issue is the contracts that blow up in a team's face. Look at Chris Davis's contract, Stephen Strasburg, Anthony Rendon. Teams and fans don't want that type of contract where a team is on the hook for $100's of millions of dollars and get 0 results from them. I mean you could even look at Trout's contract as a bad deal because of the injuries he's had in recent years. He was paid for how he performed at his peak, not how he is performing now. 

    I almost think that more teams are going to start to move towards incentive based contracts that include hardware, plate appearances, wins, HR's, or really anything. It shows the player that they are committed to that player for a baseline, but if they overperform they get tremendous bonuses, but if they get hurt or underperform, they still got a decent baseline to collect. 

    So with those motivations in mind, what seems reasonable to me for some of the guys listed in the article?

    Taj -
    If you're Taj, you're not making TOO much money yet (maybe... 4M next year?). and it's been a long time since your draft signing bonus (750k in 2018). You've earned 3-4M over your baseball career so far, and the position you play often has career altering injuries. Getting some guaranteed money and a big upfront check probably sounds pretty nice, especially with the unknown of the lockout.

    If you're the Twins, you've seen flashes of brilliance, some injuries, but nothing too bad. Taj is certainly in your medium term plans at least, with his 3 years of team control remaining and he's the best performing pitcher on your roster that has control beyond 2027. 

    If Taj continues on his 50th percentile path (injury free), he could expect to make something like 4M, 9M, 14M ($27M total) over the next three years and maybe $20M per year in free agency.

    So what's a number that both sides probably feel ok about?

    What about something like 4/38 + Team Option in year 5 - With years like:
    2027 -  2M+5M signing bonus, 
    2028 - 8M
    2029 - 10M
    2030 - 13M
    2031 - 20M Team Option
      

    Prielipp - 
    If you're Connor you finally had a mostly healthy year. The Twins have you under control for 6 more years, the first 3 of which you'll be making around the league minimum. You know your injury history and that 1.8M signing bonus you got in 2022 was nice, but it's probably mostly gone. How's my arm going to hold up? I need some guaranteed money.

    If you're the Twins. Yay! He was finally healthy and pitched.... pretty well. He showed flashes. He also showed some flushes. I'm not too interested in guaranteeing this guy too much money with his injury history, but his upside is pretty undeniable. Let's give him some reasonable money, but also set ourselves up for some upside if things click for Connor and he stays relatively healthy. 

    What about something like 5/22 + Team Options in years 6-8 - With years like:
    2027 -  1M+2M signing bonus, 
    2028 - 4M
    2029 - 4M
    2030 - 5M
    2031 - 6M
    2032 - 8M Team Option (would be his last year of team control)
    2033 - 12M Team Option
    2034 - 18M Team Option

    From the Twins perspective that maybe feels a touch generous, but it seems like something Prielipp could say yes to and having those options at the end give the Twins some upside to pair with the risk.

    17 minutes ago, Whammy said:

    If Taj continues on his 50th percentile path (injury free), he could expect to make something like 4M, 9M, 14M ($27M total) over the next three years and maybe $20M per year in free agency.

    So what's a number that both sides probably feel ok about?

    What about something like 4/38 + Team Option in year 5 - With years like:
    2027 -  2M+5M signing bonus, 
    2028 - 8M
    2029 - 10M
    2030 - 13M
    2031 - 20M Team Option
      

    I think you need guarantee the $27M to get 2030 at $20M. 4 years, $48M with a $25M option for 2031. Another shot at free agency at age 31.

    14 minutes ago, TheLeviathan said:

    Young players in MLB deserve to hit free agency much, much sooner than they do.  I imagine this will be a major outcome of the CBA negotiations.

    Read: There's no way in hell any agent is signing off on anything in this uncertainty.

    I think that's probably true for guys who still have 1 year or less of  service time, but guys like Taj are far enough along that I doubt they will see a benefit from new CBA language around service time. 

    11 minutes ago, TheLeviathan said:

    Young players in MLB deserve to hit free agency much, much sooner than they do.  I imagine this will be a major outcome of the CBA negotiations.

    Read: There's no way in hell any agent is signing off on anything in this uncertainty.

    I definitely agree with you on that. It is crazy to think from being drafted at 18, spending 5 years in the minors, you can then be added to the 40 man, then spend another 3 seasons in the minors, then have 6 years to FA could make you 31-32 when hitting the market for the first time. Now if there were to happen a lot things would have to have gone wrong in your development (injuries, not meeting expectations, lockouts, anything really). But there are definitely players this happens to (Sabato) would be a good one to point out.

    2 minutes ago, Whammy said:

    I think that's probably true for guys who still have 1 year or less of  service time, but guys like Taj are far enough along that I doubt they will see a benefit from new CBA language around service time. 

    They will if service time gets cut in half before some form of free agency. 

    1 minute ago, MackMan said:

    I definitely agree with you on that. It is crazy to think from being drafted at 18, spending 5 years in the minors, you can then be added to the 40 man, then spend another 3 seasons in the minors, then have 6 years to FA could make you 31-32 when hitting the market for the first time. Now if there were to happen a lot things would have to have gone wrong in your development (injuries, not meeting expectations, lockouts, anything really). But there are definitely players this happens to (Sabato) would be a good one to point out.

    The NHL does it right.  Based on the age you're drafted the team is given a certain number of fixed years of control before restricted free agency happens.

    The MLBPA would be fools not to be pushing for something like that.

    Comps for Walker Jenkins

    Julio Rodriguez 12 years $209M

    Jackson Merrill 9 years $135M

    Roman Anthony 8 years $130M

    Pete Crow Armstrong 6 years $115M

    Corbin Carroll 8 years $111M

    $14-17M in average annual value.

    Offer him the Jackson Merrill deal and call it good.




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