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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