December 8, 1987: Four years and one day after making him the Reds first big free agent acquisition, the Reds trade outfielder Dave Parker to the Oakland A’s for starting pitcher and future Reds ace Jose Rijo and reliever Tim Birtsas.

Parker’s best Reds season had come in 1985 when he finished second in MVP balloting after hitting .312 with 34 home runs and 125 rbi, 42 doubles, a .551 SLP, and a .916 OPS (149 OPS+). He led the league in rbi, doubles, total bases, and intentional walks. He finished fifth in MVP voting in 1986 when he hit .273 with 31 home runs and 116 rbi, again leading the league in total bases, but his OPS+ slipped to 117 (OPS was .807). He slipped a little more in 1987 when he hit .253 with 26 homers, 97 rbi, and a .744 OPS (92 OPS+) and his defensive performance had also been declining now that he was 36 years old.

Parker still had a few more productive years remaining and finished 11th in MVP voting in the American League while with the Oakland A’s in 1989 (.264/22/97 with .741 OPS) and 16th in MVP votes with the Milwaukee Brewers in 1990 (.289/21/92 with .781 OPS). His final season came in 1991.

The Reds had young outfielders in place ready to replace Parker, namely Kal Daniels, Eric Davis, Paul O’Neill, and Tracy Jones. All the outfield prospects were at least a decade younger than Parker and all were talented players.

For Parker, the Reds received their next ace pitcher in Jose Rijo. Rijo had reached the majors at age 19 with the New York Yankees in 1984, but had struggled in his first four major league seasons, going 19-30 with a 4.75 ERA (83 ERA+) with the Yankees and Oakland A’s before joining the Reds.

Rijo made an immediate impact in Cincinnati, going 13-8 with a 2.39 ERA at age 23 in his first Cincinnati season (1988). Fighting of injuries in 1989, he was 7-6 with a 2.84 ERA, but came back in 1990 to go 14-8 with a 2.70 ERA in the season of the Reds’ first World Championship since the Big Red Machine days in 1976. Rijo was named the World Series MVP after going 2-0 with an 0.59 ERA against his former team, the Oakland A’s. He allowed only nine hits and struck out 14 in 15 1/3 innings of work in the Series.

Rijo had one of his best seasons in 1991, going 15-6 with a 2.51 ERA, leading the league in WHIP (1.077) and finishing fourth in Cy Young Award voting. He finished fifth in Cy Young voting in 1993 when he was 14-9 with a 2.48 ERA and leading the league with 227 K’s on a poor Reds team that finished 73-89. Injuries slowed him over the next couple of years before “retiring” following the 1995 season. However, Rijo worked his way back and returned to the majors to pitch parts of both the 2001 and 2002 seasons with the Reds, making the unusual move of returning to the majors after missing five seasons from ages 31-35.

With the Reds, Rijo was 97-61 with a 2.83 ERA (139 ERA+) in ten seasons. Overall, he was 116-91 in 14 seasons with a 3.24 ERA (121 ERA+).

The Reds also received lefty Tim Birtsas in the deal and Birtsas helped the Reds as a lefty reliever/spot starter from 1988-90. In three seasons with the Reds, Birtsas was 4-8 with a 3.93 ERA in 107 games (five starts). In five major league seasons, Birtsas was 14-14 with a 4.08 ERA.

December 8, 1991: Two years and two days after acquiring him, the Reds trade erstwhile closer turned starter Randy Myers to the San Diego Padres for Bip Roberts and minor leaguer Craig Pueschner.

Myers had been a star reliever for the New York Mets and the Reds, having finished fifth in Cy Young Award voting for the 1990 Reds World Championship team when he was 4-6 with a 2.08 ERA and 31 saves. Myers had slumped in 1991 and had moved to the starting rotation for the only time in his 14-year major league career in an attempt to shake the slump and help an ailing Reds rotation. Myers was 6-13 with a 3.55 ERA in 1991 with Rob Dibble (3-5, 3.17 ERA, 31 saves) assuming the closer role in 1991. Myers regained his Cy Young form as a reliever, finishing eighth in Cy Young voting with the Chicago Cubs in 1993 and fourth with the Baltimore Orioles in in 1997. For his career, Myers was 44-63 with a 3.19 ERA and 347 saves.

For Myers, the Reds received diminutive (5-7, 150) IF-OF Bip Roberts who had been underrated in his days with the Padres due to his utility nature of being able to play multiple positions. While with the Padres, Roberts had played every position on the field except for pitcher, catcher, and first base. From 1988-91 with the Padres, Roberts had hit .298 with a .771 OPS (115 OPS+), including hitting .309 with 46 stolen bases in 1990 before slumping to .281 in 1991.

The Reds traded for Roberts and he proceeded to have his best major league season in 1992. Roberts was named to the all-star team and finished eighth in MVP voting after hitting .323 with 34 doubles, 45 stolen bases, and an .826 OPS (132 OPS+). He tied former Red Woody Williams’s record of ten consecutive hits and went 2-2 in the all-star game.

Roberts was hurt and slumped in 1993, hitting only .240 with a .625 OPS and was granted free agency at season’s end and played for five different teams over the next five seasons before retiring after the 1998 season. With the Reds, Roberts batted .294 with 70 steals in two seasons and posted a .754 OPS (108 OPS+). In 12 major league seasons, Roberts batted .294 with a .737 OPS (100 OPS+). Pueschner never played in the major leagues.

December 8, 2005: The Reds traded fan favorite first baseman Sean Casey to the Pittsburgh Pirates for lefty pitcher David Williams.

The Reds had acquired Casey in a trade on March 30, 1998, the day before opening day for the previously announced Reds opening day starting pitcher, Dave Burba. After starting slowly, Casey won the first base job and became a three-time all-star for the Reds. Known as “The Mayor” for his friendly demeanor, Casey batted .305 in eight seasons with the Reds, with 118 homers and 604 rbi with an .834 OPS (114 OPS+). His two best Reds seasons were 1999 (.332, 42 doubles, 25 homers, 99 rbi, .938 OPS) and 2004 (.324, 44 doubles, 24 homers, 99 rbi, and a .915 OPS). However he slumped in 1995 to .312 with nine homers (.795 OPS) at age 30 and the Reds traded Casey to his hometown Pittsburgh Pirates.

However, Casey did not last long in Pittsburgh. With the Pirates losing and possessing a large contract (especially for Pittsburgh) and Casey batting .296 with only three homers in 59 games, Casey was dealt to the Detroit Tigers. Casey only hit .245 with five homers in 53 games for the Tigers that season, but he hit .529 during the World Series with two home runs. Casey played two more seasons before retiring after hitting .322 for the Boston Red Sox as a part-time player in the 2008 season.

For his 12-year career, Casey hit .302 with 130 home runs and an .814 OPS (109 OPS+). The Reds received lefty Dave Williams in return for Casey their trade with the Pirates. Williams had his best season in 2005 when he was 10-11 with a 4.41 ERA in 25 starts. However, Williams didn’t fool anybody in Cincinnati, going 2-3 with a 7.20 ERA in eight starts, allowing nine homers in 40 innings before the Reds traded him (and cash) to the New York Mets for reliever Robert Manuel. Manuel would pitch a total of three games and 4 1/3 innings for the Reds before being traded to the Seattle Mariners for outfielder Wladimir Balentien who was granted free agency by the Reds in November, 2010. Balentien had hit .264 with three homers for the Reds in 2009. For his career, Williams was 22-31 in six seasons with a 4.83 ERA (91 ERA+).