After completing high school, Estrada was signed by the Milwaukee Braves as an amateur free agent on September 27, 1956. Prior to the start of the season, Estrada was sent from the Braves to the Baltimore Orioles in an unknown transaction.
With the Orioles
Chuck made his major league debut with the Orioles two seasons later, on April 21, 1960, in front of a crowd of 9,377 at Memorial Stadium. Estrada came in relief for starting pitcherSteve Barber in the 5thinning, and pitched two innings of one-hit ball with five strikeouts. Estrada spent the beginning of the season coming in relief, but he later joined the young Orioles starting pitching rotation, which also featured Steve Barber, Milt Pappas, Jerry Walker and Jack Fisher. Estrada's rookie season was perhaps the best season of his career. He pitched in a total of thirty-six games, and started twenty-five of them. He tied with Jim Perry for the American League lead with 18 wins that season. Only four other pitchers since had led their respective league without winning more than twenty games in the season. Estrada also was on top of the American League in hits allowed per nine innings, and finished with a twelve complete games, 144 strikeouts and a 3.58 earned run average. The All-Star Estrada finished second in the Rookie of the Year voting, falling distantly behind Orioles teammate Ron Hansen. He placed 12th in the American League Most Valuable Player Award voting, but he did win the year's TSN Pitcher of the Year Award. Estrada also was on the Topps All-Star Rookie Roster under the category of right-handed pitcher. Estrada had another successful season in, pitching in thirty three games for the Orioles. He had a 15-9 record, a 3.69 earned run average and 160 strikeouts in 212 innings of work. He again led the league in hits allowed per nine innings. However, Estrada again showed signs of wild pitching, as he issued a league-high 132 walks, thirty-one higher than that of his rookie season. He again placed second in the league by hitting ten batters in the season, finishing only one lower than the leader, Jim Kaat, of the Minnesota Twins. The next season was disastrous for Estrada, as he led the league with seventeen losses. He only collected nine wins on the season, and his ERA ballooned to 3.83. He had 121 walks in 223.1 innings, finishing a close second behind Los Angeles Angels rookie southpawBo Belinsky. Estrada's woes did not end, though. The following season, Estrada pitched in only eight games during the season. On June 8, 1963, Estrada suffered an elbow injury with bone chips and a spur in his right elbow, and was done for the season. The following season, Estrada came in as a relief/starting pitcher for the Orioles. It seemed the elbow injury had affected Estrada's pitching. He pitched only 54.2 innings that season, but he posted a 3-2 record with a 5.27 ERA.
Across the league
Estrada did not pitch the following season, and he was sent to the California Angels by the Orioles as part of a conditional deal two months prior to the start of the season. Just weeks into the 1966 season, he was returned by the Angels to the Orioles. A day later, he was sent packing again, this time to the Chicago Cubs. The Cubs gave Estrada a shot as a starting pitcher on June 14, 1966, but he pitched less than an inning, giving up three hits and four earned runs and also hitting a batter. The Cubs then sent him to the bullpen and used him in relief for the remainder of the 1966 season. His stats only worsened, as he pitched a career-worst 7.30 ERA in only 12.1 innings of work. The 28-year-old Estrada was released by the Cubs on November 30, 1966. That same day, he was picked up by the New York Mets as a free agent. The first game Estrada pitched as a Met was on April 13, 1967. Estrada came in the sixth inning to relieve Tom Seaver on his major league debut, and Estrada pitched two innings of hitless ball. He picked up the win in the first start of Tom Seaver's Hall-of-Fame career. However, the rest of the season did not fare as nicely. In 22 innings of work, Estrada gave up 28 hits, walked 17 batters, and had a 9.41 ERA. So ended Estrada's major league baseball career as a player. After retiring from the majors, Estrada found employment in the majors again, but this time as a pitching coach. He served as pitching coach for the Texas Rangers, San Diego Padres, and Cleveland Indians.
