Apologies for the jump scare, Red Sox fans, but: Rusney Castillo. Don't get up in arms just yet — this is still a piece about what it will take to sign Roman Anthony long-term — but it's important to remind ourselves that even the most "surefire" prospects aren't sure things.
You can't just hand a guy making his MLB debut $300 million dollars and forget about it for the next 15 years. There's going to be risk from both sides when making a deal, but a sense of security, too.
Now, Anthony, the best prospect across all of baseball, is a marquee player already. His arrival signals the official start of the "Big Three" era in Boston, and introduces arguably the most talented player to the team since the ill-fated Mookie Betts trade.
So, with all this hype and pomp and circumstance surrounding him, it's only natural that the Red Sox would want to keep Anthony in town for the next decade-plus. What would it take for them to do that?
A Roman Anthony-Red Sox extension would have to be historic
The Red Sox actually have some recent history in extending young player on long-term deals ahead of their arbitration years.
Last spring, they signed starting pitcher Brayan Bello to a six-year, $55 million extension. Bello was fresh of a campaign where he authored a 4.24 ERA in 157.0 innings at 24 years old. With four years of team control left (including one pre-arb year), the team bought out two of Bello's free agent years in order to keep him on the roster through the pitcher's 20s.
Just a few weeks later — and, notably, after the start of the regular season — Boston handed utility man Ceddanne Rafaela an eight-year, $50 million contract. Rafaela wasn't even 40 games into his MLB career, but after spending a few years building up a reputation as one of the game's top 50 prospects, the Red Sox chose to buy out all his pre-arb and arbitration years, as well as the first two seasons of free agency (they also added a ninth-year club option).
And, of course, this season, the Red Sox came to terms on an eight-year, $60 million contract with Kristian Campbell, the first member of the Big Three to make their MLB debut. His deal includes a few club options that could bring the total value of the deal over $100 million.
It's worth noting that Anthony had a more prominent prospect profile than any of those players, ranking inside as the best prospect in baseball on most aggregate lists this offseason. Rafaela is arguably the best comparison because of his age (23) at the time he signed his deal and position, but it's actually another wunderkind from the Brewers who may have set the benchmark for Anthony.
Jackson Chourio famously signed an eight-year, $82 million extension with the Milwaukee Brewers prior to ever playing a game in the big leagues. It was a huge gamble that paid off big time (at least so far), though Chourio was and younger (19) than Anthony is now (21).
Considering he'd be sacrificing his first few years of free agency (and the middle of his prime) on any six-plus-year deal, it's not outrageous to think he and the Red Sox might price those seasons at exorbitantly high values, especially given the inflation of star contracts in baseball right now.
So, would eight years and $100 million get the job done? It'd be a huge stretch to hand a guy with practically no MLB service time nine figures, even one as good as Anthony, but would he be willing to take less?
The Red Sox have been as aggressive as any team at getting their young stars locked up long-term. Perhaps a Mayer extension could set the bar for Anthony to beat, though he'll probably set the bar for future No. 1 prospects if and when he signs a contract with the Red Sox.