There have not been a lot of really good players who get a chance due to being selected in the Rule 5 Draft. Roberto Clemente is the best example, being selected by the Pirates from the Brooklyn Dodgers in 1954. I'm sure the Dodgers want that one back. Johan Santana, Kelly Gruber, Jose Bautista, Fernando Vina, and Shane Victorino are some other players who have done well since being selected. Boston does not have nearly as much success. In fact, very few players Boston has picked up in the Rule 5 Draft have had much of any success in the Majors.
Since I started watching the team, only four players selected by Boston in the Rule 5 Draft have played in the Majors with the Red Sox. Boston lost Wil Ledezma, Ryan Pressly, and Josh Fields, who had some success in the Majors, over the years. Looking back prior to that, there really were not any big name players selected either.
And now, counting down the best players to make it to the Majors selected by the Red Sox since 1991, based on their Major League success:
5. Matt White
4. Adrian Brown
3. Adam Stern
Stern was a personal favorite of mine since he was a fellow Nebraska Cornhusker, though he is originally from Canada. Stern had been in the Braves system and had a decent season in Greenville, yet the Braves did not add him to their 40 man roster. Stern spent the entire 2005 season in Boston, either on the active roster or on the disabled list and ended up appearing in 36 games, hitting .133/.188/.333, though he did get his first home run and stole a base. That is obviously the problem with the Draft, Stern was clearly not ready and it likely stunted his growth as a player, because he never played more than 10 games in the Majors again. Stern played in just 10 games with Boston in 2006 and was traded to the Orioles for Javy Lopez (the catcher).
2. Lenny DiNardo
The most likely players to be selected in the Rule 5 Draft are relief pitchers, particularly lefties, and DiNardo is a good example. Selected in the 2003 Draft from the Mets, DiNardo appeared in 22 games over the course of the season, though he was also injured for a time. He struck out 21 and walked 12 in 27.2 innings and had a 4.23 ERA. He made it through the season with Boston, was granted free agency and re-signed, and was able to go back to the minors in 2005. He made it back to Boston later that season and had a 1.84 ERA in eight games, striking out 15 and walking five in 14.2 innings. He had a rough season in 2006 though, going 1-2 with a 7.85 ERA and a significantly decreased strikeout rate. DiNardo was reasonably successful with Oakland in 2007 when he was 8-10 with a 4.11 ERA. He played another season for Oakland and one for the Royals.
1. Vaughn Eshelman
It is pretty close between Eshelman and DiNardo for the title here. DiNardo likely had the best individual season and had the longest Major League career, but Eshelman was ever so slightly better, mostly on the strength of his decent 1995 season. The southpaw Eshelman was selected in the 1994 Rule 5 Draft from the Baltimore Orioles. He won his first three Major League games in 1995, only giving up three earned runs in 18.2 innings. It was a pretty decent start to the season. He finished the season 6-3 with a 4.85 ERA. He walked 36 and struck out 41 in 81.2 innings. He had an identical 6-3 record in 1996, but with a 7.08 ERA. He was mostly used in relief, making it into 29 games out of the bullpen versus ten starts. He was then 3-3 with a 6.33 ERA in 1997, again splitting time between the rotation and bullpen. He was left exposed in the expansion draft and was selected by the Devil Rays, but he never made it back to the Majors.
Unfortunately, the best player Boston selected in the Rule 5 Draft was immediately traded away. Marwin Gonzalez was selected in the 2011 Draft from the Cubs but was traded to the Astros for someone named Marco Duarte. Gonzalez has been with Houston ever since and has been a fairly reliable utility player. In 2015, he hit .279/.317/.442 with 12 home runs and 34 RBIs. Duarte, who had been a very good pitcher in the Mexican League, never made it to the Majors.
This season, Boston's Rule 5 selection was Josh Rutledge, an infielder who has already played for Boston the last couple of seasons. He is expected to be another utility infielder option along with Brock Holt and Marco Hernandez. They also lost Justin Haley, a pitcher in Pawtucket. There is a possibility he could be returned.
So, the Rule 5 Draft is not terribly exciting. Certainly not historically for the Red Sox. None of these players are household names, and none should be. It takes a lot of luck for a player from the Rule 5 Draft to turn into a good player. There have been a few, but Boston has not been that lucky.