1991 would see Giles join the Kinston Indians of the “A+” Carolina League, hitting .310 over 125 contests. He scored 71 times and collected 47 RBI. He started out the following season with Kinston (42 games, .264, 18 RBI), joining the “AA” level Canton-Akron Indians in the Eastern League (23 games, .216). He spent the entire 1993 season with the AA outfit, improving his average to .327 with eight home runs, 18 stolen bases , and 64 RBI.
In 1994, Giles joined the Charlotte Indians, Cleveland’s “AAA” affiliate in the International League. He averaged .313 at the plate, while seemingly discovering his power stroke, collecting 16 home runs and 58 RBI over 128 games. He played with the “AAA” level Buffalo Bisons of the American Association in 1995, hitting .310 with 15 home runs and 67 RBI. He also made his first major league appearance in Cleveland, scoring six times and going 5-for-9 with a home run and three RBI in a short September callup.
1996 would see Giles split his time between the Bisons and the Indians. He hit .355 at the major league level over 51 games, with 14 home runs, five round-trippers and 27 RBI. He also drew 19 walks and only struck out 13 times in 143 plate appearances. He would eventually play in parts of four seasons for the Tribe, hitting .284 with 39 home runs and 157 RBI over 299 games. After the 1998 season, the Indians sent him to the Pirates for pitcher Ricardo Rincon (7-8, 3.73 over four seasons in Cleveland).
In 1999, Giles put together his best season to date, doubling his career home run total. He hit .315 with 33 doubles, a career high 39 home runs (NL eighth) and 115 RBI (NL 10th), walking 95 times (NL seventh) with 80 whiffs in 627 plate appearances. He placed 19th in the season ending NL MVP voting. He could also boast a .418 OBP (NL eighth) and a .614 SLG (NL fifth). He batted third and played all three outfield positions (mostly center field, never at the same time). On May 3rd, he parked two in the cheap seats, making five RBI in a 9-8 win over the San Francisco Giants. Pittsburgh posted a 78-83 record, finishing the season in third place in the NL Central.
2000 would see Giles again finish 19th in the NL MVP vote and be rewarded with his first all-star invitation. He repeated his .315 batting average, raising his OBP to .432 (NL fourth) with 114 walks (NL second) and only 69 strikeouts. He scored 111 runs (NL 10th), hit 37 doubles, seven triples (NL seventh), and 35 home runs for 123 RBI (NL fifth). He also ranked second in the NL with 14 outfield assists. He batted third or cleanup all season, appearing nearly equally in all three outfield positions. On April 6ht, he went 5-for-5 with three runs, a triple and two home runs for four RBI in a 10-1 win over the Houston Astros. The team finished in fifth place in the division, at 69-93.
In 2001, Giles continued to put up good numbers for the cellar dwelling Pirates. In 160 games (NL eighth), he hit .309 with 116 runs scored (NL 10th), 37 doubles, seven triples (NL eighth), and 37 home runs with 95 RBI. He also stole 13 bases and walked 90 times against only 67 strikeouts. He made his second straight all-star appearance and finished 24th in the NL MVP voting. In the first game of a doubleheader on July 28th, he got a chance to live up to every eight year old’s dream. Down by a score of 8-5 against the Astros, he hit a bottom of the ninth, two out, bases loaded walk-off home run. He also hit a single and a double earlier in the game. Despite this small show of heroism, the Pirates finished at 62-100, a distant last place NL Central finish.
2002 would see Giles finish 13th in the NL MVP vote. He hit .298 in 153 contests, with 95 runs scored, 37 doubles, 38 home runs (NL sixth), 103 RBI, and career highs with 15 stolen bases and a mind-boggling 135 walks (NL second). He also struck out only 74 times in 644 plate appearances and finished with an NL second best 6.6 offensive WAR, his .450 OBP and .622 SLG were career highs, and also good for second best in the NL. He ranked third in the league with 13.2 AB per HR and led the league with 13 assists from LF, batting third and cleanup. On September 27th, he scored five runs, walking twice, hitting a double and two home runs, stealing a base, and finishing with six RBI in a 13-3 win against the Chicago Cubs. The Bucs posted a 72-89 record, finishing in fourth place in the six-team NL Central.
2003 would start out with Giles hitting .299 through Pittsburgh’s first 105 games. He hit 30 doubles and 16 home runs for 70 RBI, with 85 walks and a .430 OBP. The Pirates batting him mostly in the third spot and in left (although he collected a handful of starts batting cleanup and/or in center field). He hit two home runs for three RBI in a 5-4 win over the Arizona Diamondbacks on May 10th. On August 26th, the Pirates traded him to the San Diego Padres for leftfielder Jason Bay (six seasons with the Pirates, 719 games, 139 home runs, .281 batting average, 452 RBI), pitcher Oliver Perez (four seasons, 21-28, 4.59), and a player to be named later (minor leaguer Corey Stewart).
In seven seasons with the Padres, Giles hit .279 with 83 home runs and 415 RBI, never again approaching the level of productivity seen when he was with the Pirates. He led the NL with 119 walks in 2005, finishing that season ninth in the NL MVP race.
All-Time Statline: Five seasons, 715 games, 782-for-2541, .308/.426/591, 501 runs, 174 doubles, 26 triples, 165 home runs, 506 RBI, 40 stolen bases, 519 walks, 338 strikeouts, 25.2 wins above replacement.
Next man up: another part of the family – a Pirates all-star centerfielder through most of the 70’s.