Risk, legacy and the future of the Red Sox: Five questions about Chris Sale's extension

Of the top 30 players in baseball, five have signed extensions this week alone. But a few factors help make Chris Sale's deal unique. Brad Mills/USA TODAY Sports

The free-agent season might have been sluggish once again, but the extension season is smoking hot. With ESPN's Jeff Passan reporting that the Boston Red Sox have agreed to a five-year extension with ace lefty Chris Sale -- worth somewhere in the neighborhood of $145 million -- yet another established star has decided to forgo the possibility of future free-agent riches.

According the extension tracker at MLB Trade Rumors, 20 players have now agreed to extensions since the end of last season. Let's break them into groups:

The "so good we've seen enough" group: Eloy Jimenez, White Sox; Brandon Lowe, Rays. Both are rookies -- Jimenez has yet to make his major league debut -- but both have impressed their organizations so much they bought out the entirety of each player's controllable years. For the players, it gets them cash sooner and allows them to forgo the relative uncertainty of arbitration in favor of income certainty. Both deals reportedly include a couple of team option years beyond the six-year term of the extension.

The "you don't need no stinking arbitration" group: Jorge Polanco, Twins; Jose Martinez, Cardinals; Miles Mikolas, Cardinals; Jose Leclerc, Rangers; Alex Bregman, Astros; Blake Snell, Rays; Whit Merrifield, Royals; Max Kepler, Twins; Luis Severino, Yankees; Aaron Nola, Phillies; Raisel Iglesias, Reds. These players have performed so well during their pre-arbitration seasons their clubs decided to commit to them through their arbitration years and, in most cases, beyond. (Martinez's case is a little different.)

The "free agency, what is it good for?" group: Aaron Hicks, Yankees; Nolan Arenado, Rockies. Rather than taking their first crack at free agency after the 2019 season, Hicks and Arenado signed on for seven more seasons with their current organizations.

The "if it ain't broke don't fix it" group: Paul Goldschmidt, Cardinals; Mike Trout, Angels; Carlos Carrasco, Indians; Chris Sale, Red Sox. A quartet of star-level performers coming off early-career extensions, all of whom decided the grass is not necessarily greener on the other side of Free Agency Street. Goldschmidt, of course, made his commitment to the Cardinals before he has even made his regular-season debut for the club.

The future free-agent lists are losing luster fast. Based on the ratings I compiled for my position tiers series, nine of the top 30 players in baseball have signed extensions since the end of last season -- five of them this week alone.

(Note: These lists don't include the extension-of-an-extension Clayton Kershaw agreed to with the Dodgers after the season. Kershaw would make it 10 of the top 30.)

In that context, here are five questions that leap to mind about Boston's commitment to Sale.