When it comes to the Rule 5 Draft, the Phillies, like other clubs, have uncovered a few gems. Conversely there have been some draft duds for every team.
Navigating through Baseball-Reference.com revealed the first such Draft took place in 1903, the same year as the first World Series. Starting in '52, the Draft has been part of baseball's annual Winter Meetings. Eligibility rules and Draft prices varied throughout the years. At one time, umpires were drafted from the Minor Leagues.
Phillies' first
The Phillies' first selections came in 1905 when they chose four: pitcher John McCloskey (from Omaha Rourkes), pitcher Lew Moren (Atlanta Crackers), infielder Paul Sentell (Macon Brigands) and August Hoff (Savannah Pathfinders). Moren spent four seasons with the Phillies, McCloskey and Sentell parts of two unproductive seasons, while Hoff never saw the Major Leagues.
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Hall of Famer
Selecting a franchise-record 12 players in 1910, the Phillies came up with a Hall of Fame pitcher and 11 names never to be seen again.
Right-hander Grover Cleveland Alexander, selected from the Syracuse Stars for $750, wound up with a 190-91 record with the Phillies (1911-17; '30). He was the ace on the Philadelphia's first pennant winner ('15) and among the first Baseball Hall of Fame induction class ('39). Alexander was easily the best pitcher the Phillies have drafted and will probably ever draft.

The Rule 5 Draft included one other Hall of Fame legend, outfielder Roberto Clemente, selected from the Dodgers organization in 1954 by the Pirates.
Flyin' Hawaiian
In terms of overall success, center fielder Shane Victorino may be the most successful Phillies selection, at least for a position player. Drafted from the Dodgers organization in 2004 for $50,000, Shane went on to an eight-year Phillies career that included a World Series championship, National League pennant, three other playoff seasons, two All-Star selections and three Rawlings Gold Glove Awards for defensive excellence.

Here's Pinky
Next to Victorino is third baseman Arthur (Pinky) Whitney, who was taken from the New Orleans Pelicans (1927). He played for the Phillies, '28-33 and '36-39. As a rookie in '28, Whitney drove in 103 runs, which remains a club rookie record. Among the club records he holds for a third baseman in a season: RBIs (124 in '32), hits (207 in '30) and highest batting average (.342 in '30). His .307 lifetime average is the highest for any franchise third baseman.
Other notables
1928: RHP Phil "Fidgety Phil" Collins ('29-35). Won 72 games in his seven Phillies seasons. Nickname came from his nervous traits on the mound.
1959: C Clay Dalrymple ('50-68). Behind the plate for 100-plus games six straight years starting in '61. Heavyweight boxing champ in college. 
1960: RHP Jack Baldschun ('61-65). Averaged 66.6 appearances, won 39 and saved 59 for the Phillies. His out pitch was a screwball. 
1989: 3B Dave Hollins ('90-95; 2002). Switch-hitter who was an All-Star in '93, the year Philadelphia won the pennant.
1991: C Todd Pratt ('92-94; 2001-05). Played on '93 NL champions, was there for closing of the Vet and opening of Citizens Bank Park.
This decade
2010: INF Michael Martinez 
2011: CF Ender Inciarte 
2013: RHP Kevin Munson 
2014: CF Odubel Herrera and LHP Andy Oliver
2015: OF Tyler Goeddel and LHP Daniel Stumpf
Lost were:
2011: LHP Lendy Castillo (Cubs)
2013: RHP Seth Rosin (Mets)
2016: LHP Hoby Milner (Indians),
2017: OF Carlos Tocci (White Sox, traded to Rangers)
Big payday
The 1980 World Series champion Phillies were built through a strong Minor League system during the 1970s.
During the 1980 Draft held in Dallas, the club lost a franchise-high four players off Triple-A Oklahoma City's roster: outfielder George Bell (Blue Jays), catcher/outfielder Orlando Sanchez (Cardinals), left-hander Carlos Arroyo (White Sox) and right-hander Jim Wright (Royals). A $200,000 payday.