Xander Bogaerts is currently hitting .339 and leading the American League in hits with 57. Although his numbers don't show it right now, Mookie Betts is still one of the more electric players in the MLB. If you combine the 2016 salaries of both players, they equal $1.216 million; a bargain to say the least.
Bogaerts is set to hit the free agent market after the 2019 season, while Mookie will hit free agency after the 2020 season. However, it would be a lethal mistake to let either of these players even approach free agency. Although the Red Sox have some time to figure out their extensions, the longer they wait, the more difficult and expensive it will become.
Given that both players are only 23-years-old, and are already demonstrating above average play, a lengthy extension should be the route the Red Sox take. According to MLB Trade Rumors extension tracker, since 2011, 70% of extensions for players with less than 5 years experience have been announced from February to March.
Another issue that comes into play is that Xander Bogaerts is represented by Scott Boras, who has been known to be a tough negotiator. With the numbers Bogaerts is putting up, a seven year contract would not be out of the question. If the Red sox can land him at 7-years, $70-$77 million, it would be a steal, however, with Boras as his agent, he could get well north of those numbers. For reference, here are the top 10 shortstop salaries in the MLB for 2016.
As good as Mookie Betts is, I'd have to believe that Bogaerts would be the priority. Especially since the Red Sox have had a revolving door of shortstops since Nomar left. By no means do the Sox have to choose between extending the two, and I'm sure Mookie will see a generous extension also.
Among all outfielders in the MLB, Betts ranks 90th in salary, with Jackie Bradley right behind him at 92nd. As is the case with Bogaerts, Betts has shown a lot of promise, even at a young age, and stands to only improve his game as he matures. Given all the factors, I wouldn't be surprised to see a 6- or 7-year extension for Betts as well, somehwere in the neighborhood of $68-70 million. A contract like this would put Betts at about $10 million average, still well outside top 10 salaries for outfielders, and once again a steal for the Sox.
As I said before, the longer the Sox wait, the more value these players will gain, and it will be harder to sign them to a reasonable contract. With Price having the 3rd highest salary in baseball, plus the contracts of Hanley and Pablo, the Red Sox need to sign these two for as cheap as possible. There is no doubt in my mind that they will sign Xander and Mookie, but the sooner the better.