December 15, 1900: The infamous Frank Robinson trade to the contrary, the Reds make the worst trade in franchise history when they deal future Hall of Famer Christy Mathewson to the New York Giants for end-of-the-line Hall of Fame pitcher Amos Rusie.

You can read it about it in more detail here. Suffice it to say, Rusie was 0-1 as a Red, making three appearances for them in his last games as a major leaguer. He won 246 games before joining the Reds (246-174, 3.07 ERA career). Mathewson won one game for the Reds, in 1916 after the Reds reacquired him to manage the team. Between 1900 and 1916, Mathewson won 372 games while with the Giants (373-188, 2.13 ERA career, 1-0 with the Reds).

December 15, 1920: Reds trade 1919 World Series star pitcher Dutch Ruether to the Brooklyn Robins for future Hall of Famer Rube Marquard. Marquard apparently had been made available after having been fined for scalping World Series tickets in the Robins’ seven game 1920 Series loss to the Cleveland Indians.

Ruether had been one of the best pitchers on the Reds’ 1919 World Championship team going 19-6 with a 1.82 ERA, leading the league with a .760 won-loss percentage and allowing only one home run in 242 2/3 innings that season. Ruether, an excellent hitting pitcher, also hit .261 with two doubles and three triples during that season. Ruether, a former waiver claim, was in his third major league season and had never won more than three games in a season before. Ruether had won his only decision in the World Series, carrying a 2.57 ERA in two games (14 innings) and batted .667 (4-6), with a double, two triples, and four rbi in the Series (2.214 OPS). He followed up his outstanding 1919 by going 16-12 with a 2.47 ERA and five shutouts in 1920.

Marquard was a 13-year veteran who had three 20-game victory seasons in his career. At the time of his acquisition, Marquard had a lifetime 159-124 record with a 2.74 ERA. Marquard had won 19 consecutive starts to begin the season in 1912 on his way to a 26-11 record. He definitely had star power, but he was turning 34 years of age. Ruether was just 26 and was a very good pitcher himself. The deal was made and Ruether went on to pitch seven more seasons, going 99-74 with a 3.97 ERA (100 ERA+).

Marquard pitched one season for the Reds, going 17-14 with a 3.39 ERA (105 ERA+), then was dealt to the Boston Braves with shortstop Larry Kopf for pitcher Jack Scott. With Boston, Marquard was 25-39 with a 4.44 ERA (89 ERA+). For his career, Marquard was 201-177 with a 3.08 ERA. Scott pitched only one inning for the Reds, but later was a double digit winner three times for the New York Giants. Marquard pitched well in his one season as a Red, but there’s little way to spin this trade as a Reds victory.

December 15,1959: The Redlegs trade all-star second baseman Johnny Temple to the Cleveland Indians for first baseman Gordy Coleman, second baseman Billy Martin, and pitcher Cal McLish.

It sounded like a good idea. The Redlegs were trading “high” as Temple was coming off possibly his best season for three players. The 32-year-old second baseman hit .311 with a 35 doubles, 102 runs scored, and an OPS of .809. In return, the Reds received good glove, fiery second baseman Martin, also 32, a veteran of four teams already; the 34-year-old McLish, also a veteran of four teams; and 25-year-old Coleman, a rookie of six games.

As it turned out, Temple played four more seasons and was selected to one more all-star team, but wasn’t the same player as he was with the Redlegs. With the Redlegs, Temple played nine seasons, hitting .291 with an OPS of .733 (93 OPS+). He played 13 major league seasons, hitting .284 with an OPS of .713 (91 OPS+). Martin played one season for the Redlegs, hitting .246 with a .639 OPS (74 OPS+), participated in two major brawls, and was sold to the Milwaukee Braves who also dealt him after six games in his final season. Martin had a .257 lifetime batting average with a .669 OPS (81 OPS+) in an eleven year career. McLish was 4-14 in his one season with the Reds with a 4.16 ERA. In his fifteen seasons, McLish was 92-92 with a 4.01 ERA. Coleman played eight seasons for the Reds, hitting .273 with 98 home runs. His best season was during the 1961 World Series team when he hit .287 with 26 home runs and an .845 OPS (113 OPS+). He followed up in 1962, hitting .277 with 28 homers.

December 15, 1960: In a three-way deal, the Reds trade Gold Glove shortstop Roy McMillan to Milwaukee Braves for young pitchers Joey Jay and Juan Pizarro. The Reds then trade Pizarro and pitcher Cal McLish to the Chicago White Sox for third baseman Gene Freese. This was one of new VP-GM Bill DeWitt’s first deals with the acquisition of Freese and Jay considered to have been keys to the Reds 1961 National League championship.

McMillan is considered to have been the original “Gold Glove” shortstop, but carried a weak bat (career .243 average with 72 OPS+). The Reds had also sold his double play partner, Billy Martin, to the Braves just a couple of weeks earlier. McLish, acquired one year earlier, had only gone 4-14 for the Reds. Pizarro, who was a Red for just a few minutes, had been 23-19 with a 3.93 ERA in four years with the Braves. Jay, had been a “bonus baby” signing for the Braves, but had been considered a bust, going 24-24 with a 3.39 ERA in seven seasons. Freese had already played for three times by age 25, but had a powerful bat for an infielder and could play third base.

1961 proved to be a very good year for all parties involved, except for Martin.. McMillan hit only .220 but still received MVP votes for his stellar glove work for the Braves and he played six more seasons giving him a 16-year major league career. Martin batted six times for the Braves, who then traded him to the Minnesota Twins, for whom he batted .246 in his last season. Overall, Martin played 11 seasons (for seven teams), batting .257 (81 OPS+). McLish was 10-13 for the White Sox with a 4.38 ERA (92-92, 4.01 lifetime). Pizarro had a big year for the White Sox, going 14-7 with a 3.05 ERA. He went on to pitch through the 1974 for eight different teams (nine, counting the Reds for whom he didn’t pitch), a total of 18 major league seasons with a career 131-105 record and a 3.43 ERA. His best season was 1964 when he was 19-9 with a 2.56 ERA.

Freese had a big season for the Reds, hitting .277 with 26 home runs for the 1961 National League champions. Freese’s play allowed the Reds to move Eddie Kasko to shortstop and the Reds acquired Don Blasingame early in the 1961 season to play second base as GM DeWitt completely retooled the Reds’ infield. Freese suffered a leg injury running the bases early in the 1962 season and he was never quite the same player. In twelve seasons, for six different teams, Freese hit .254 with a 115 career home runs.

Jay became a star in 1961, leading the National League with 21 wins and four shutouts and finishing fifth in MVP balloting. He was 21-10 with a 3.53 ERA and was the winner in Game Two of the 1961 World Series vs. the New York Yankees. He followed his 1961 season by going 21-14 in 1962 with a 3.76 ERA, before dropping to 7-18 in 1963 with a 4.29 ERA. In six Reds seasons, Jay was 75-63 with a 3.80 ERA. For his career, Jay was 99-91 over 13 seasons with a 3.77 ERA and 16 shutouts.

December 15, 1970: The Reds trade pitcher 1960’s ace Jim Maloney to the California Angels for pitcher Greg Garrett.

Maloney was the best pitcher of the 1960’s Reds, posting a decade mark of 134-80 with a 3.08 ERA, 30 shutouts, an ERA+ of 120 for the decade, averaging 7.9 K’s per nine innings, allowing only 7.3 hits per nine innings, and was twice a 20 game winner. However, at age 29 in 1970, Maloney tore an Achilles tendon running the bases which drove him from the game as the Big Red Machine was reaching dominance. Maloney was 0-1 in 1970 with a 11.34 ERA in seven appearances. Traded to the Angels, Maloney was 0-3 with a 5.04 ERA, finishing his career 134-84 with an ERA of 3.19. He attempted comebacks with both the St. Louis Cardinals and San Francisco Giants, but did not pitch in the majors again.

Garrett, the lefty pitcher, had an interesting background himself. He was drafted three different times in the amateur draft (1965, 28th round by Kansas City Athletics; 1966, 22nd round by the Chicago White Sox; 1967, 10th round in January secondary draft by the Atlanta Braves), but refused to sign with any of the teams. From California, he signed with the San Francisco Giants as a free agent in June, 1967, but was drafted from their minor league system by the California Angels in 1968. After having struck out 184 minor league hitters in 154 innings in 1969, Garrett made the 1970 Angels squad as a rookie. Pitching well, Garrett was 5-6 with a 2.65 ERA in 32 appearances (seven starts), with an ERA+ of 137, striking out 6.4 batters per nine innings, and allowing only 5.8 hits per nine innings at age 23.

Garrett made the 1971 Reds team out of spring training, allowing only three hits and no runs in 5 2/3 innings in his first start with the Reds, but walking seven and striking out only one. His second appearance was a three inning relief stint where he walked three more batters, striking out one and allowing four hits in nine innings. These two appearances gave him an unlikely 1.04 ERA while posting a WHIP of 1.962, walking a batters at a 10.4 rate per nine innings. Garrett was sent to AAA Indianapolis and never returned to the major leagues, retiring after the 1972 minor league season.