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Going into the 2009 Major League Baseball draft, the Los Angeles Angels of Anaheim had two first-round draft picks, as well as three supplemental first-round picks. With these five selections, they drafted two outfielders, Randal Grichuk and Mike Trout; and three pitchers: Skaggs, Garrett Richards, and Tyler Kehrer. Skaggs was the 40th overall selection in the 2009 draft, taken 15 slots after Trout. He had committed previously to play college baseball for Cal State Fullerton, but he chose to sign with the Angels on August 7, 2009, for a $1 million bonus instead.
Skaggs made his professional baseball debut on August 22, 2009, relieving starting pitcher Fabio Martinez with a scoreless sixth inning for the AZL Angels in a 2–1 win against the AZL Athletics. He pitched ten Rookie League innings that season, playing in both the Arizona League and with the Orem Owlz of the Pioneer League. Between the two teams, Skaggs posted a 1.80 ERA as a rookie. In 2010 Skaggs and Trout lived as roommates while they played for the Cedar Rapids Kernels of the Class A Midwest League, befriending each other and the family that had rented out their basement to the players. Skaggs pitched in 19 games for the Kernels that year, starting 14, and posted a 8–4 win–loss record with a 3.61 ERA during that time. Skaggs was also one of seven Kernels named to the 2010 Midwest League All-Star team.
On July 25, 2010, Skaggs was one of several players sent to the Arizona Diamondbacks in exchange for three-time All-Star pitcher Dan Haren. In exchange for Haren the Diamondbacks received pitcher Joe Saunders, prospects Patrick Corbin and Rafael Rodríguez, and a player to be named later, speculated to be Skaggs. Skaggs was not named officially at the time of the trade because Major League Baseball prohibited any player from being traded until they had played professional baseball for one full year. Therefore, while the trade was made at the end of July, Skaggs remained with the Kernels until August 7. Once Skaggs was eligible to be traded, the Diamondbacks assigned him to the Class A South Bend Silver Hawks of the Midwest League. There, he posted a 1–1 record and a 1.69 ERA in four starts and sixteen total innings. Between the two Midwest League teams, Skaggs' 2010 record was 9–5, and he posted a 3.29 ERA with 102 strikeouts.
Skaggs was assigned to the Class A-Advanced Visalia Rawhide of the California League to start the 2011 season, where he anchored the team's starting rotation. He started 17 games with the Rawhide that season, posting a 5–5 record and a 3.22 ERA while striking out 125 batters in 100+2⁄3 innings. Although Visalia finished in fifth place in the California League North Division, the league named Skaggs both a midseason and postseason all-star. On July 10, 2011, Skaggs was chosen as the starting pitcher for Team USA at the annual All-Star Futures Game. In the one inning he pitched Skaggs gave up one hit and one walk, recorded one strikeout, and left two batters on base. The next day, Skaggs was promoted from Visalia to the Double-A Mobile BayBears of the Southern League. In ten starts with Mobile, Skaggs went 4–1 with a 2.50 ERA and 73 strikeouts in 57+2⁄3 innings. At the end of the season, the Diamondbacks named Skaggs their minor league pitcher of the year.
The BayBears kept Skaggs through the beginning of the 2012 season. In thirteen starts with the team that year, he posted a 5–4 record and averaged more than one strikeout per inning. At the end of June, Skaggs was promoted to the Reno Aces of the Triple-A Pacific Coast League. There, he went 5–5 with a 2.91 ERA and 45 strikeouts, and Reno captured their first Pacific Coast League championship title. Skaggs was one of five players to appear in both the 2011 and 2012 MLB All-Star Futures games, the others being Nolan Arenado, Manny Machado, Wil Myers, and Jurickson Profar. He was not originally named to the Futures game but was selected to replace Trevor Bauer after Bauer was called up to make his major league debut.
The Diamondbacks called Skaggs up to the major leagues on August 21, 2012, to start the first game of a same-day doubleheader against the Miami Marlins. He made his MLB debut the next day, giving up two runs in 6+1⁄3 innings in a 3–2 win against the Marlins. Skaggs stayed with the Diamondbacks until he was shut down for the season on September 24, following three consecutive poor outings and a drop in his fastball's velocity. He went 1–3 in his major league rookie season, with a 5.83 ERA in six starts.
Going into the 2013 season, MLB.com named Skaggs the 10th overall MLB prospect, and the highest-rated prospect in the Diamondbacks organization. He entered spring training a contender with Patrick Corbin and Randall Delgado for the final spot in the Diamondbacks' starting rotation, but was ultimately optioned to the Aces before the start of the season. He spent most of the 2013 season with the Aces, but made one appearance with Visalia, where he recorded eight strikeouts. Skaggs also made seven major league starts with the Diamondbacks, ending the season with a 2–3 record and a 5.12 ERA. During this time, Skaggs also struggled with opioid abuse, which he disclosed to his family after the 2013 season. After this disclosure, he ceased his Percocet consumption cold turkey.
Skaggs was part of a three-team trade conducted on December 10, 2013. He and pitcher Hector Santiago were sent to the Angels, while outfielder Adam Eaton went to the Chicago White Sox. Arizona received Mark Trumbo, as well as two players to be named later. Arizona general manager Kevin Towers told reporters that the team had looked to trade Skaggs after concerns emerged over his decreased confidence, command, and pitch velocity – his fastball speed, for instance, had dropped from a high of 90.6 mph (145.8 km/h) to 88.7 mph (142.7 km/h) over the course of the previous season.
Leading into the 2014 season Skaggs was in competition for the fifth place in the Angels' starting rotation with veteran Joe Blanton. He spent spring training focusing on enhancing his fastball command and developing the other pitches in his arsenal. He also made a mechanical tweak to his pitching mechanics, returning to the larger stride that he took in high school and as a member of the Angels' farm system. Skaggs was named to the Angels' opening day roster that spring, joining a rotation that also featured Santiago, Jered Weaver, C. J. Wilson, and Garrett Richards. After going 4–4 with a 4.34 ERA in his first twelve starts, Skaggs was scratched from his scheduled June 9 start against the Oakland Athletics. Manager Mike Scioscia revealed that Skaggs was suffering from a strained right hamstring and was placed on the disabled list as a precaution. He spent nearly a month on the disabled list before being activated on July 2 to start in a game against the White Sox.
On July 31, 2014, Skaggs left a potential no-hitter in the fifth inning after experiencing left forearm tightness and was relieved by Mike Morin, who lost Skaggs's no-hit bid by giving up a hit to Baltimore Orioles' batter Caleb Joseph. After MRI tests revealed a strain to the common flexor tendon of Skaggs's arm, the Angels placed the pitcher on the 15-day disabled list. On August 10 the team revealed he had sustained a partial tear of the ulnar collateral ligament and would need to undergo a season-ending Tommy John surgery to repair his arm. At the time of the injury, Skaggs had posted a 5–5 season record with a 4.30 ERA in eighteen starts. Due to his former issues with opioid addiction, Skaggs's mother and surgeon prevented him from taking any painkillers that were stronger than Tylenol 3.
Originally, Skaggs wanted to start his rehabilitation in the minor leagues during the 2015 season, but after seeing Matt Harvey of the New York Mets successfully return to the mound after eighteen months of Tommy John rehabilitation, he decided to wait until the 2016 season to pitch again. Skaggs was assigned to the Triple-A Salt Lake Bees at the start of the season to build his endurance before returning to the Angels. A bout of biceps tendinitis in April set back Skaggs's recovery, but by July, he was able to begin rehab assignments with the Class-A Advanced Inland Empire 66ers and with the Bees. He made his first major league start since undergoing surgery on July 26, 2016, pitching seven scoreless innings in a 13–0 win against the Kansas City Royals. Striking out five, Skaggs allowed three hits, and his only walk of the night was Alcides Escobar. Skaggs finished his first season back with a 3–4 record and a 4.17 ERA.
Injuries continued to trouble Skaggs's time with the Angels. On April 28, 2017, he left a game against the Texas Rangers in the fifth inning with muscle pain, later diagnosed as a Grade 2 oblique muscle strain with a typical recovery time of ten to twelve weeks. The injury kept him out of the lineup for fourteen weeks after he suffered a recurrence of oblique pain shortly before a scheduled rehab assignment in July. He returned to the mound on August 5, throwing 83 pitches and giving up three runs on six hits in four innings. Skaggs was limited to eighty-five innings across sixteen starts in 2017. He went 2–6 with a 4.55 ERA and 76 strikeouts. Throughout the 2018 season, a recurrent adductor muscle strain placed Skaggs on the disabled list on three separate occasions. Between the second and third instances, the injury seemed to impact his performance: after nineteen starts with a 2.62 ERA, Skaggs gave up 17 runs in 6+2⁄3 innings across two starts. Despite the injury, the 2018 season proved to be the best of Skaggs's career, as he set career highs with eight wins, twenty-four starts, 125+1⁄3 innings pitched, and 129 strikeouts. His 0.84 ERA in June set an Angels record for all pitchers with a minimum of thirty innings. Skaggs went 8–10 for the year, with an overall ERA of 4.02.
On April 12, 2019, Skaggs sprained his left ankle in the fourth inning of a game against the Chicago Cubs when he landed in a divot on the pitcher's mound at Wrigley Field. He attempted to pitch through the injury, but he could not push off the foot, and his fastball speed dropped by 5 mph (8.0 km/h) almost at once. After recording the third out of the inning, Skaggs was removed from the game and placed on the injured list. He returned from the injury on April 26, pitching five scoreless innings against the Kansas City Royals and seeing fastball speeds up to 94 mph (151 km/h). Upon his return Skaggs led the Angels' rotation with seven wins and 78 strikeouts. Skaggs continued to suffer from physical pain which he managed through self-medication. In the final start of his career Skaggs threw 91 pitches in 4+1⁄3 innings against the Oakland Athletics, and sportswriter Nathan Fenno observed him to be less effective than he had been throughout the season. In total Skaggs posted a 28–38 win–loss record and a 4.41 ERA for his major league career, striking out 476 batters in 520+2⁄3 innings pitched.