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He pitched for the United States national baseball team in the 2019 WBSC Premier 12 tournament in November 2019.

On August 28, 2018, he was ruled out for the season after undergoing knee surgery. He ended the season 7–11 with an ERA of 5.33 in 27 starts. In ​158  ⁄3 innings, he struck out 108.

On December 20, 2018, Richard was designated for assignment.

On December 30, 2018, Richard was traded to the Toronto Blue Jays for minor league outfielder Connor Panas. Richard was placed on the injured list on March 29, 2019, with an injury to his right knee. Richard made his season debut on May 23 against the Boston Red Sox. He pitched 4 innings, allowing 1 run on 2 hits in a no decision. Pitching for Toronto in 2019, he was 1-5 with a 5.96 ERA in 10 starts covering 45.1 innings, and pitching for their AAA affiliate Buffalo he was 0-0 with a 5.06 ERA in two starts covering 5.1 innings. On September 12, 2019, his 36th birthday, the Blue Jays released Richard.

Richard was a fixture in the San Diego rotation in 2017, leading the team with 197​⁄3 innings over his 32 starts, including two complete games. He allowed a league-high 240 hits with a 4.79 ERA, but was third in the Major Leagues with a 59.2% ground ball rate and posted a personal best 6.9 strikeouts per 9 innings. In 2017 he led the major leagues in allowing opposing batters the highest batting average on balls in play (.351). He tied for the major league lead in pickoffs, with seven, while allowing four stolen bases and having 10 caught stealing. Richard was the Padres' nominee for both the Heart & Hustle Award and the Marvin Miller Man of the Year Award. In September, the Padres extended Richard through 2019 with a two-year deal.

In 2016, Richard was used as a situational leftie out of the bullpen until he was placed on the disabled list on June 21 with a blister on his finger. He returned to the bullpen in July but was designated for assignment on July 26 when Aroldis Chapman was added to the roster and then released on August 3. With the Cubs in 2016, Richard pitched to a 6.43 ERA in 14 innings over 25 games. The Cubs went on to win the World Series, and Richard was presented with a World Series ring when he returned to Wrigley Field with the Padres in 2017.

On August 6, 2016, the Padres signed Richard to a major league deal. He made his Padres return debut in the San Diego bullpen upon the first week of August. After two appearances out of the bullpen, Richard joined the San Diego rotation and made nine starts over the remainder of the season. With the Padres in 2016, he pitched to a 2.52 ERA over 53​⁄3 innings with 34 strikeouts. On December 20, Richard signed a one-year contract to stay with the Padres.

On July 3, 2015, Richard was traded to the Chicago Cubs for cash. His first start for the Cubs was a 7–2 victory against the Miami Marlins on July 4. After going 1–0 in 3 appearances (2 starts), Richard was outrighted to AAA. After 1 start in AAA, Richard was called up to start on Sunday, August 2, versus the Brewers. Richard got the victory, pitching 6 innings of 1 run ball, striking out 3 and walking none. He was designated for assignment a second time a day later. After electing for free agency, Richard re-signed with the club two days later to take a bullpen role when reliever Rafael Soriano developed a sore shoulder. Richard pitched to a 3.38 ERA over 21​⁄3 innings with two walks and one home run out of the bullpen over the rest of the year, and finished the 2015 season with a 3.83 ERA overall.

Richard underwent Thoracic Outlet Syndrome surgery in February 2014.

On July 30, 2014, Richard agreed to a minor league deal with the Arizona Diamondbacks. Richard appeared in 4 starts, 3 in AA and 1 in AAA.

On December 3, 2014, Richard signed a minor league deal with an invite to spring training with the Pittsburgh Pirates. Through 9 starts, Richard had an ERA under 2.50 in just 50 innings pitched with their Triple-A affiliate.

After his surgery in 2014, Richard's velocity dipped a bit, his fastball reading between 88-92 MPH in 2015.

The following spring, Richard joined the Wolverines baseball team and pitched well. In his one season in Ann Arbor, Richard pitched 21 games, mostly as a reliever and compiled a 0–1 record with a 2.43 ERA, a 1.20 WHIP, and 27 K's in 33.1 IP, good for a 7.29 K/9 innings ratio. The Wolverines were 42–19 that season and finished 4th in the Big 10 with a 17–12 conference record. They were the 3rd seed in the Atlanta Regional of the College Baseball Tournament but were eliminated in the 2nd round of the Regionals, losing both games to South Carolina by 1 run. After starting his baseball career with moderate success, Richard dropped his football scholarship at Michigan and focused on baseball full-time.

On February 16, 2013, Richard and the Padres avoided going to arbitration, both sides agreeing on a $5.24 million deal for one season.

Richard opened 2013 as the Padres number 2 starter, but had a rough beginning to the season, posting an 8.54 ERA in his first six starts. An intestinal virus forced Richard to push back a start in late April, and he was then placed on the disabled list on May 5 when the virus flared up again. Richard returned on May 27, but continued to struggle. On June 1, Richard pitched 2 innings in relief to earn his first win of the season in a 17 inning affair against the Blue Jays that the Padres won 4–3. On June 21, Richard injured his left shoulder and left the game after making only two pitches. He underwent shoulder surgery on July 15, ending his 2013 season. He finished with a 2–5 record in 11 starts with a 7.01 ERA and 24 strikeouts in 52​⁄3 innings. On October 28, 2013, he refused an outright assignment and elected free agency.

In 2012, Richard resumed his role in the Padres starting rotation. At the end of the season, he was the unanimous pick as the Padres Pitcher of the Year by writers covering the team. He had a 14–14 record with a 3.99 earned run average. His 33 starts were tied for second in the National League (NL) and he was fourth with ​218  ⁄3 innings pitched.

Richard is a pitch to contact pitcher, inducing groundouts at over a 49% rate through 2012. He also has pitched well at Petco Park, posting an ERA under 3.30 each year from 2010 to 2012.

In 2011, Richard regressed slightly, posting a 5–9 record with a 3.88 ERA while his strikeout-to-walk ratio dropped to 1.39 K/BB from 1.93 K/BB in 2010. A left shoulder strain forced Richard to the disabled list in July and later required arthroscopic surgery, ending his season.

Richard started 33 games for the Padres in 2010, building a 14–9 record and a 3.75 ERA over 201​⁄3 innings. On September 21, 2010 Richard threw his first career shutout, giving up eight hits, two walks, and recording six strikeouts in a win against the Los Angeles Dodgers along with a golden sombrero at the plate, striking out four times.

In 2009, Richard was initially used out of the bullpen, but then moved to the starting rotation on May 12, making 14 starts for the White Sox that year. On July 31, 2009 Richard was traded along with Aaron Poreda, Adam Russell and Dexter Carter to the San Diego Padres for 2007 Cy Young Award-winner Jake Peavy.

Richard made his first start for the Padres on August 1, 2009, recording no decision in 5​⁄3 innings at home against the Milwaukee Brewers. Richard compiled a 5–2 record with a 4.08 ERA over 12 starts in his partial season with the Padres.

From 2009–2013, Richard's pitching repertoire consisted of a four-seam and a two-seam fastball (90-95 MPH), a changeup, a slider, and an occasional curveball. Since 2011, he has relied more on his two-seam fastball than his four seam, with this he has induced more than a 50% groundball rate each year since 2011.

After playing for the Rookie-level Great Falls White Sox and Class-A Kannapolis Intimidators in 2005, the Intimidators and Class-A Advanced Winston-Salem Warthogs in 2006, the Warthogs in 2007 and the Class-AA Birmingham Barons and Class-AAA Charlotte Knights in 2008, Richard made his major league debut with the White Sox on July 23, 2008.

The White Sox selected Richard in the 8th round of the 2005 Major League Baseball Draft. He was the 2nd player from Michigan drafted, the first being Chris Getz, also selected by the Sox in the 4th round.

Richard was redshirted for the Wolverines football team his freshman year. In 2004, he battled for the starting quarterback spot on the team but lost it to Chad Henne. Richard was the Wolverine's #2 quarterback that season, but he saw limited action, mostly in blowout wins over Miami (Ohio), Indiana, and Northwestern. Richard appeared in 4 total games for the Wolverines in 2004, only attempting 15 passes for 8 completions and 52 total yards.

Richard accepted a scholarship to play football and baseball at the University of Michigan in the fall of 2003.

Clayton Colby Richard (born September 12, 1983) is an American professional baseball pitcher who is a free agent. The Chicago White Sox selected Richard in the 8th round of the 2005 Major League Baseball Draft. He has played in Major League Baseball (MLB) for the White Sox, San Diego Padres, Chicago Cubs, and Toronto Blue Jays.