The Red Sox have been the most successful team of the past two decades, and that is thanks in part to clever drafting. While they haven't always successfully signed future stars out of the draft, they have at least recognized future talent. Here are the Red Sox top five drafts since 2000.
The Red Sox captured a championship in 2007, as well as drafting an impressive class. Four of the players they drafted have since combined for six All-Star selections and three World Series Championships. Unfortunately, none of those actually came with the Red Sox. Relief pitcher Hunter Strickland was traded two years later in a mid-season deal for first baseman Adam LaRoche, who left in the ensuing offseason. He would be a solid rotational piece for a contending Giants team, winning one World Series with them, as well as the Nationals this past season.
Another reliever, Ryan Pressly, also signed with the Red Sox but was picked in the 2012 Rule 5 draft by the Twins. A regular and integral part of their bullpen, Pressly was then traded to the Astros in 2018 and was named an All-Star with Houston last year for the first time. They also drafted catcher Yasmani Grandal, who unfortunately chose not to sign a professional at that point in his career. He has been a two-time All-Star, the most recent also being last year.
Then there was the prize of the draft, first baseman Anthony Rizzo whom they took in the sixth round. Rizzo was part of a package deal in 2010 for Padres All-Star Adrian Gonzalez, and then was traded less than two years later to the Cubs. He became Chicago's top prospect, and of course, is now considered one of the best first basemen in the game.
The 2002 draft just barely beat out the 2007 draft, based on the fact that the success of the players actually came in Boston. A combined seven All-Star selections and three World Series, this draft class produced three key players. Brandon Moss, an outfielder and first baseman, played only a season and a half with the Sox before leaving as part of the 2008 Manny Ramirez trade. He has since jumped around the league, playing for seven total teams, but did have an All-Star selection a few years prior to his retirement after the 2017 season.
Starter Ricky Romero did not sign with the Sox out of the draft, and had a very short career with the Blue Jays once he hit the majors. He played only five years, with his peak being an All-Star in 2011 at the age of 26. His quick downfall resulted mainly from knee problems, having to undergo multiple surgeries following his final campaign in 2013.
But the brightest light in the draft was undeniably Jon Lester. He spent nine successful years in Boston, with three All-Star selections, two championships, and two top-five finishes in the Cy Young Award race. He was traded in 2014 in a largely forgotten deal with the Athletics for Yoenis Cespedes, and Lester signed with the Cubs the following offseason. With Chicago he has added two All-Star appearances and another World Series victory as he continues to pitch in the MLB at the age of 36.
The 2004 draft is very similar to the 2007 one, as they both saw one superstar and two decent role players getting selected by Boston. Reliever Cla Meredith spent only one year in Boston, getting traded for catcher Doug Mirabelli, who would be part of two championships in Boston. Meredith was not as lucky, as throughout his career he was at best a solid reliever on bad Padres and Orioles teams.
10th round pick Steve Pearce has had an interesting relationship with the Red Sox. He was drafted by the Sox but did not sign a professional contract until he was picked one year later by the Pirates. He has been with seven teams in his career, most recently with the same team who originally drafted him: the Boston Red Sox. He is best known for his impressive play in the 2018 World Series, where he was named MVP for his three home runs on four hits during the five games against the Dodgers. He was one of many Sox players who struggled last year, and is without a contract heading into next season.
But the star of the show was second-round pick Dustin Pedroia. There is not much that hasn't been said about the little second baseman, but I will still mention his 2008 MVP award, four All-Star selections, four Gold Gloves, and two World Series victories. He has remained a crucial player up until 2018, where injuries began to catch up to him. Pedroia is still on the road to recovery, and his future remains in doubt. Perhaps the delay in the season's start allows him to finally get to full health, but even that isn't certain.
The 2011 Draft is the most recent draft on the list, as it is hard to rank recent drafts where prospects haven't made the MLB yet. This draft boasts the best player on this entire list, as well as the most key players so far. Pitchers Noe Ramirez and Matt Barnes have both been solid pitchers in the MLB, but Barnes has spent his entire career on the Sox, while Ramirez spent a little over two seasons. Barnes was important to the Red Sox 2018 championship, and is one of the most reliable pieces in their bullpen.
Travis Shaw played only two seasons in the majors with Boston, as he was sent away in a trade to acquire Tyler Thornburg, who at the time was one of the best relievers in the league. In the first year after the trade Shaw made it look like it was a huge mistake as he batted .273 with 31 homers. But he has since been on the decline, and it is sad to see the once-promising career slowly fall apart.
With one of four first-round selections the Red Sox grabbed defensive wizard Jackie Bradly Jr. He has been one of the greatest defensive centerfielders in the league, which is unfortunately paired with an inconsistent bat. The one year JBJ batted over .250, when he batted .267 in 2016, he was named an All-Star. All he needs is a consistent bat, and he would be one of the best overall players in the league. But despite how important he's been to the team, Bradley was not the best outfielder in this draft class.
Mookie Betts was taken relatively unknown in the fifth round, but would see more and more attention as he impressed in the minors. It only took three years for him to join the majors, and an additional year to become the starter. He has never batted under .260 in his career, and this sturdy bat is why he has been named to four All-Star games in addition to four Gold Gloves, three Silver Sluggers, one World Series win, and an MVP. He was traded to the Dodgers this offseason as the Red Sox looked to cut current and future costs to their payroll.
This is a very packed draft class, full of many solid players. It doesn't have one defining superstar like the prior drafts, but the sheer number of great players more than makes up for that. Kirby Yates, Pedro Alvarez, and Jason Castro all were selected to an All-Star game in their careers, yet all three didn't sign for the Red Sox following their selections.
Another player who chose to not sign following their selection by the Sox in this draft was Charlie Blackmon. With the Rockies, he has been a four-time All-Star, two-time Silver Slugger, and even won the Batting Title in 2017. The center fielding wizard has shown no signs of slowing down, but does appear to be looking for a change of scenery from a disappointing Colorado team.
Clay Buchholz arrived through this draft and has since seen plenty of ups and downs in his career. The righty managed a no-hitter, two All-Stars, and was crucial to the 2013 World Series championship. He has struggled since that championship, having only a couple of good seasons in the past six years. Jed Lowrie also saw his name called in the first round, and spent four years with the Sox before being traded. He has had a relatively silent career but did become an All-Star in 2018.
Lastly, we saw Jacoby Ellsbury taken with the 23rd overall pick in the draft. He was actually selected three years earlier in the 23rd round by the Rays, but he didn't sign. He has been an All-Star, Gold Glover, Silver Slugger, and two-time World Series Champion, all with the Red Sox. He signed with the Yankees, and to Red Sox fan's pleasure hasn't reached those same heights since he began making over $20 Million per year. He was released after last year's season ended. But despite his disappointing ending, he still was a great way to top off a very deep and talented draft class.