A new frontier in contract extensions was breached on Monday when Astros first base prospect Jon Singleton became the first player to sign a multi-year, multi-million-dollar extension in advance of his major league debut. The 22-year-old Singleton, who is hitting .267/.397/.544 with 14 home runs for Triple A Oklahoma City, agreed to a five-year, $10 million contract with three club options and will play his first game for Houston, which is off today, on Tuesday. The options and bonuses in Singleton's contract could increase the total value of the deal to $35 million over eight years.
Singleton is the first minor leaguer to sign a major extension, but not the first to be offered one. Fellow Astros prospect George Springer and Pirates outfield prospect Gregory Polanco were both recently offered seven-year contracts worth a reported $23 million and $25 million, respectively, with the understanding that their promotion to the major leagues would follow. Both declined. Springer, who turned down his offer last September, was called up in mid-April, the delay pushing back his free agency by year. Polanco, who rejected his offer earlier this year, remains in Triple A despite a .350/.411/.548 batting line over 241 plate appearances, as the Pirates appear to be waiting to promote Polanco to make sure he is not eligible for salary arbitration as a Super Two player in January 2017.
It must have taken extraordinary resolve for both Springer and Polanco to decline those offers. Put yourself in their shoes: You're in your early 20s, riding buses in Triple A on the verge of your lifetime dream of making the major leagues. You know you have the talent to become a superstar in the majors, a status that would yield you tens if not hundreds of millions of dollars in salary and endorsements. You also know that one fluke play could wipe out your major league career before it even starts and that even the best prospects can be humbled by major league pitching. Nothing is guaranteed to anyone, but suddenly your organization comes to you and offers you the money and the promotion at the same time. Maybe it's less than you could earn if everything goes perfectly, but it's still tens of millions of dollars guaranteed for signing your name, and you'll still hit free agency in your prime, leaving open the possibility of a far greater payday to come. It's financial security for life and a lifetime dream realized in an instant.
It's also a huge potential savings for the team. Springer and Polanco refused to sell themselves short, and Springer has likely already profited from that decision. The Astros won't be able to lock him up for $23 million over seven years now that he's hit .309/.404/.702 with 10 home runs over his last 24 major league games.
Singleton needn't have emerged as a superstar to earn in excess of his guaranteed $10 million in his first five major league seasons. Just look at fellow first baseman Mark Trumbo. The Diamondbacks' slugger is a deeply flawed player with a career .297 on-base percentage. He is also an All-Star for his home run prowess, which helped him reach a $4.8 million settlement in his first year of arbitration last winter, less than two months after being traded to Arizona from the Angels. He has made $6.245 million in his first four full major league seasons, and if he merely repeats that number in arbitration this coming offseason he'll top $11 million in his first five years in the majors. As for Singleton's potential $35 million over eight years, Prince Fielder, another slugging first baseman who debuted at the same age as Singleton, made $23 million in his seventh full major league season alone and more than $80 million in his first eight full seasons combined. Fielder may be a lofty comparison point, but it's still informative that he made more than twice as much in his first eight seasons as Singleton can under his new contract.
Singleton has more reason to be wary of risk than Springer and Polanco, however. A self-described marijuana addict, Singleton was twice suspended in the minors for using the drug, the latter coming in early 2013. In March he admitted that in his depression following his suspension last year, he self-medicated with alcohol. There's an entire conversation to be had about the appropriateness of those suspensions, but it remains true that marijuana is on Baseball's list of Drugs of Abuse. Singleton has triumphed greatly over his addictions this year, as evidenced by his performance at Triple A, but there's no doubt a very real fear in his mind that his career could be derailed by subsequent moments of weakness. Given that, it's possible to paint Singleton's new deal as the result of a team preying upon a vulnerable young player, but the fact of the matter is that if he wasn't the first player to sign such a contract, someone else would have been, and likely soon. As evidenced by the Springer and Polanco offers, this sort of contract was in the air, and someone was going to take the bait. It's hard to blame Singleton for blinking first. Even if the Astros exercise all three options, they'll only have him for one more year than they would have under the traditional six-year system (the current season counts as a year on his contract, but not as a full season of service time toward his free agency, so he wouldn't have been a free agent until after the 2020 season anyway). He'll still be a free agent at the age of 30, and may yet land that nine-figure payday. The worst case scenario for Singleton is that his major league career goes bust and he's left with $10 million. We should all be so unfortunate.