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  • Alex Kirilloff, and the Truth About Scott Boras and Contract Extensions


    Matthew Trueblood

    Some Twins fans object to the idea of Alex Kirilloff opening the season with the Twins, on the premise that agent Scott Boras will proscribe any contract extension to keep Kirilloff around beyond 2027. That’s simply not true.

    Image courtesy of © Geoff Burke-USA TODAY Sports

    Boras has been one of baseball’s most influential and successful agents for about 30 years, and it’s fair to say that he’s earned that reputation by ensuring that his clients are paid what they’re worth. Often, that does mean taking them to free agency, where teams have to bid against one another and a player can gauge their true market value. However, in the last decade, Boras has negotiated no fewer than eight contract extensions for clients prior to their reaching free agency, including some very relevant precedents for a theoretical Kirilloff deal.

     

    In early 2011, Boras and client Carlos González—an electrifying bat-first corner outfielder who batted left-handed—agreed to a seven-year, $80-million deal with the Colorado Rockies, when González was still four years from free agency. Later that year, just months before Angels pitcher Jered Weaver was due to hit free agency, he and Boras signed a five-year extension with the team.

     

    In March 2013, Carlos Gómez and Boras agreed to a three-year extension to keep him with the Brewers, when he was a year from free agency. Weeks later, Boras and client Elvis Andrus agreed on an eight-year deal with the Rangers, when Andrus was still several years from free agency. In 2016, Boras client Stephen Strasburg signed an extension with the Nationals in May of what would otherwise have been his walk year.

     

    More recently, Boras has negotiated long-term deals for clients José Altuve and Xander Bogaerts, each of whom was a year from free agency at the time. The idea that Boras is inflexibly averse to any pre-free agency deal is false and misleading.

     

    If your preferred way of dealing with Kirilloff would be for the Twins to sign him to an immediate extension like the ones to which the White Sox inked outfielders Eloy Jiménez and Luis Robert, you’re doomed to disappointment. Boras has never signed a client up for a long-term deal before they reached two years of service time.

     

    That’s not a problem, though. The Twins shouldn’t want to sign Kirilloff to such a deal so soon, anyway. As I wrote in advocating that he open the season on the roster, Kirilloff might not turn out to be worth keeping beyond 2026. The Twins will have a much clearer idea of his value in a couple of years, just as he will. The team will also be able to use that time to determine what they have in Trevor Larnach, what Max Kepler’s aging curve will look like, and whether Kirilloff’s long-term defensive home is in the outfield or at first base. All of that is relevant—even crucial—in setting the price at which an extension would make sense.

     

    If they do decide that Kirilloff is extension-worthy, be it in late 2022 or early 2026, there’s every reason to believe that Boras and Kirilloff will be receptive to conversations about such a deal. None of the examples cited here involved teams that had overwhelming leverage over the player in question. The special circumstances that allowed each deal to fruition weren’t all that special, really. In each case, a team demonstrated a serious (beyond monetary) commitment to both the player themselves and building a winning team around them. In each case, their offer reflected that fact, such that (while the terms can still be characterized as team-friendly) Boras could confidently sign off on his client’s choice. In each case, the player responded to the team’s behavior by wanting to stay, which helped ensure both sides would do what was needed to finish the deal.

     

    This is what we should want from all parties, when it comes to building lasting relationships between teams and their young players. The Twins have been one of the league’s model franchises in just this regard, especially over the last two years. Vilifying Boras for his style is silly; using Kirilloff’s choice to retain him as a reason to manipulate his service time is a red herring.

     

    This team, this player, and this agent can easily find common ground, if and when the time comes. In the meantime, the Twins should make the decision that maximizes their chances to win a close division in 2021, and the one that gives them the best chance to evaluate their options for the longer term.

     

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    I think we’re seeing some congestive dissonance type behavior when it comes to people drawing these conclusions about Krilloff.

     

    Some people love this front office. Nothing wrong with that at all. But, they are placing their own moral outlook onto the operations of the Twins front office. It’s like anthropomorphism in a way. Because they’re a good person, I like the Front Office, they must be good people. If they’re good people, there’s no way they would do something that may seem unethical like manipulate a players service time for financial reasons.

     

    Thus, in order to reconcile with the potential Kirilloff situation, there has to be something else at play. It has to be that he isn’t ready for the majors, despite just watching him rocket the ball around the field again the Astros pitching staff in a playoff game. Or, it has to be some nefarious motive from a lurking agent, and the Twins are merely manipulating his service as a wise defense from getting ripped off in some way. They’ll just never accept that they’re screwing this kid over, and making the team worse, for financial gain.

     

    All of this said, we say see Kirilloff start in left field on opening day. But the absolute refusal to buy that the FO could possibly do something unbecoming is wild.

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    Great article!!! The best thing for ownership and team value is to win. Win in 2021, especially in October. Winning the world series makes AK's service time irrelevant. AK is a S.T.U.D. Play him 157 games, starting on opening day. I am 100% confident that he is our best LF and the FO knows it as well. Let's play ball!!!

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    It's cognitive dissonance, with an "i," if we're scoring for accuracy. Just throwing that out there :)

     

    I'm one who has expressed my support for the current front office, but it's not because I necessarily think they're exemplary humans. I'm not in a position to say. I do think they've shown signs of being exemplary baseball + businesspeople. As such, they know what Kirilloff may be capable of and are in the best position to make the call on what to do with him. I trust them not to needlessly antagonize one of our potential future cornerstones. If Kirilloff does earn a spot in camp and they still hold him back, I'll chalk it up to the front office deciding the extra year of control outweighs the ill will they'll earn.

     

    Interestingly, Buxton may serve as an interesting test case of the wisdom of holding back a player. Will he let bygones be bygones and re-up? We'll soon find out.

     

    Ultimately, I think the system needs to be changed so that no one -- ballplayer or front office -- is put in this position. I think that's something we all agree on.

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    I think we’re seeing some congestive dissonance type behavior when it comes to people drawing these conclusions about Krilloff.

    Some people love this front office. Nothing wrong with that at all. But, they are placing their own moral outlook onto the operations of the Twins front office. It’s like anthropomorphism in a way. Because they’re a good person, I like the Front Office, they must be good people. If they’re good people, there’s no way they would do something that may seem unethical like manipulate a players service time for financial reasons.

    Thus, in order to reconcile with the potential Kirilloff situation, there has to be something else at play. It has to be that he isn’t ready for the majors, despite just watching him rocket the ball around the field again the Astros pitching staff in a playoff game. Or, it has to be some nefarious motive from a lurking agent, and the Twins are merely manipulating his service as a wise defense from getting ripped off in some way. They’ll just never accept that they’re screwing this kid over, and making the team worse, for financial gain.

    All of this said, we say see Kirilloff start in left field on opening day. But the absolute refusal to buy that the FO could possibly do something unbecoming is wild.

    Why is doing something within the rules...rules agreed to by the players union...”unethical”. It’s either good for the club in the long term or it’s not. Nothing more, nothing less. The notion that this is any more “unethical” than a player deciding to leave teammates and an organization that have treated him well for any amount of additional money...well, it’s not a terribly objective stance. One is try to maximize long term value to the club...in other words, do their job. The other is doing the best for himself and his family. Nothing unethical about either regardless of whether we like the rule or the outcomes.

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    Why is doing something within the rules...rules agreed to by the players union...”unethical”. It’s either good for the club in the long term or it’s not. Nothing more, nothing less. The notion that this is any more “unethical” than a player deciding to leave teammates and an organization that have treated him well for any amount of additional money...well, it’s not a terribly objective stance. One is try to maximize long term value to the club...in other words, do their job. The other is doing the best for himself and his family. Nothing unethical about either regardless of whether we like the rule or the outcomes.

    Actually it's a lot more complicated than that. The teams that engage in service time manipulation are getting close to violating actual legal principles of contract law. Here's a paper from the Boston College Law Review that lays it out pretty well starting on page 23:

     

    https://lawdigitalcommons.bc.edu/cgi/viewcontent.cgi?article=3528&context=bclr

     

    Cases like Kris Bryant have just enough grey area for teams to avoid punishment in front of an arbitrator, but it's still a real legal question. Not really comparable to feelings about a free agent player signing with a new organization -- there's nothing to legally arbitrate there.

     

    It's why teams don't option good players when they fall out of contention, even though they technically could within the CBA rules -- they would almost certainly lose those cases in front of an arbitrator, as a violation of the implied obligation of good faith in their contract.

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    I don't think fans hate Boras as much as how MLB is structured.  With some teams having 60M to 70M payroll and others 200M which teams are likely to get the cream that has risen to the top?  Yep the Yankee's, Dodgers, Nationals etc.  So when teams like the Indians can't keep a homegrown player like Lindor because he alone would be a quarter to a third of their payroll as a fan that sucks. The guy you watched come up. watched perform in the clutch and become one of the best players in baseball is ripped from your team because your team can cannot compete financially.

     

    Do I think the players get screwed more often than not and Boras is at least somewhat of an equalizer sure, but while I am a fan of baseball players I am a greater fan of the team I root for. So when Boras moves my favorite player to the highest bidder and I am rooting for a team that gets supplemental picks it doesn't feel fair when Boras moves player Z to team X simply because my team can't afford the player.

     

    Is that selfish on my part? sure, but so is wanting your team to win and others to lose, it is part of what makes you a fan, wanting your team to win.  If you are a top revenue generating team you love Boras because he prices out half the league most of the time so they have less competition for great players.  If your team is one of the bottom revenue teams probably not so much because he makes it hard to keep your star players and field a competitive team.

     

    It isn't so much about hating Boras as it is how the market system in baseball is setup.  Boras is doing his job and doing it well but market inequalities do make him look villainous to fans when he moves the best players on their team to another.

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    I don't think fans hate Boras as much as how MLB is structured.  With some teams having 60M to 70M payroll and others 200M which teams are likely to get the cream that has risen to the top?  Yep the Yankee's, Dodgers, Nationals etc.  So when teams like the Indians can't keep a homegrown player like Lindor because he alone would be a quarter to a third of their payroll as a fan that sucks. The guy you watched come up. watched perform in the clutch and become one of the best players in baseball is ripped from your team because your team can cannot compete financially.

     

    Do I think the players get screwed more often than not and Boras is at least somewhat of an equalizer sure, but while I am a fan of baseball players I am a greater fan of the team I root for. So when Boras moves my favorite player to the highest bidder and I am rooting for a team that gets supplemental picks it doesn't feel fair when Boras moves player Z to team X simply because my team can't afford the player.

     

    Is that selfish on my part? sure, but so is wanting your team to win and others to lose, it is part of what makes you a fan, wanting your team to win.  If you are a top revenue generating team you love Boras because he prices out half the league most of the time so they have less competition for great players.  If your team is one of the bottom revenue teams probably not so much because he makes it hard to keep your star players and field a competitive team.

     

    It isn't so much about hating Boras as it is how the market system in baseball is setup.  Boras is doing his job and doing it well but market inequalities do make him look villainous to fans when he moves the best players on their team to another.

    I agree with this post, but I'll nitpick and say that Boras isn't the one who moves a player. His client, the player, makes the final decision about whether to stay or go. However, Boras has deservedly acquired the reputation of being more aggressive about negotiating for his clients than most agents, presumably because a larger contract for his client gets him a larger cut. Also, I suspect that a player who puts the dollar amount of his contract as his highest priority is one who is more likely to choose Boras as his agent, which in turn makes it more likely Boras will be involved in these situations. It's kind of like a feedback loop. That said, in these situations Boras and the player are not being unethical. They are simply playing by the rules, exploiting the (inequitable) system.

    I think more extensive revenue sharing would benefit not only the majority of fans but also the majority of players. When only a few teams have much greater power to pay large contracts it means the few players getting those contracts benefit at the expense of other players. Giving all teams similar financial wherewithal would mean that player salaries will be more equitable, not just within a given team but within MLB as a whole. It also would mean players in one team's system have similar chances of succeeding as a player in another team's system, both in terms of on-field performance and in terms of salary. Think of it this way--compare a utility player for Kansas City to a utility player for the Dodgers. The two probably have similar performance profiles and so forth but which player will be more likely to have a higher salary and chance of postseason success? Which borderline minor league player will have a greater chance to be promoted to the majors, one in the KC system or one in the Dodger system?

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    It's also important to realize that just because someone signs with Boras it doesn't necessarily mean that he's really their primary guy, too. He's a big-time agent with a lot of clients...Kirilloff will get some attention but not undivided.

     

    The extensions before making their debut have a lot more value to guys who were lower draft picks. Kirilloff got a healthy signing bonus and it makes it easier to bet on himself. He also doesn't need to support his family.

     

    I think he's going to be a great, great hitter so I'd love to get him locked down and not have to deal with any arbitration games and hold him through at least 1-2 years of FA...but we'll see how it goes. 

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    MLB has a lot of dumb rules and agreements and Boras is smart enough to see the loopholes and weaknesses and exploit them for his players.  He has done an amazing job.   I get angry at some of the tactics, but I get angry at some of the FO people too.  The Seattle situation really opened up a window on many FO personnel. 

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    People need to remember too that it is not up to Boras if and when a client signs a deal.  He tries to get and it is up to his client if they will sign it.  I have been stating for weeks that with the CBA coming up I expect major changes to it because over the last decade how teams are spending money has shifted a ton.  

     

    The old rules of signing deals for players until they are in late 30's are no longer happening.  There is advantage to players signing bigger deals earlier on.  If the Twins want to piss Kirilloff, then manipulate his service time, then you will never get a good deal with him.  At least I sure would never sign with a team that screwed me over to save a little bit of money, I would want to stick it to them later.  

     

    Put the best team on the field, worry about 6 years from now later on.  If he crushes for years and gets too expensive to resign well you get 6 good years.  If he does not then who cares about 1 extra year.  If Kirilloff hits well enough and healthy he should break with team.  We are talking about keeping him down for a few weeks to have one more year of control over him, because we expect he will be so good that we will not be able to resign him.  

     

    Bryant with Cubs was well publicized for this.  There was huge talks about him not being tendered this year because he has been struggling last couple years.  We have no clue how well Kirilloff will be playing in 5 or 6 years.  

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    Actually it's a lot more complicated than that. The teams that engage in service time manipulation are getting close to violating actual legal principles of contract law. Here's a paper from the Boston College Law Review that lays it out pretty well starting on page 23:

     

    https://lawdigitalcommons.bc.edu/cgi/viewcontent.cgi?article=3528&context=bclr

     

    Cases like Kris Bryant have just enough grey area for teams to avoid punishment in front of an arbitrator, but it's still a real legal question. Not really comparable to feelings about a free agent player signing with a new organization -- there's nothing to legally arbitrate there.

     

    It's why teams don't option good players when they fall out of contention, even though they technically could within the CBA rules -- they would almost certainly lose those cases in front of an arbitrator, as a violation of the implied obligation of good faith in their contract.

    Good faith has a lot of gray area.

    1. AK is not the best defensive LF (Cave)

    2. Rooker was up at the MLB and got injured. 

    3. Is AK better than a platoon of Cave/Rooker?

    4. Maybe the Twins want to use AAA to improve his defensive abilities in LF and 1B.

    5. Maybe the Twins are going with the hot bat at the end of ST or not.

     

    The Twins could use a few of the above to justify AK being sent down.

     

    The Rays did the same with Evan Longoria until he signed a long, team friendly contract.

     

    The Twins Front Office needs to put the TEAM ahead of any player. Getting an extra year is much more important than a few weeks.

     

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    The Twins could use a few of the above to justify AK being sent down.

    Yes. I wasn't referring to Kirilloff specifically, just service time manipulation in general.

     

    Kirilloff would be less blatant than the Kris Bryant situation -- pretty much every 2021 prospect has a better case for being sent down than Bryant did, since there was no 2020 minor league season. And it's a fairly easy calculation for any team to trade a few weeks for an extra year of a position player under the current set-up. (Although as these cases add up, plus comments like those from the Seattle FO, the league may pay for it eventually, in the form of new CBA rules and/or labor strife!)

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