Herrera was signed by the Texas Rangers as an international free agent in 2008 at age 16. He began his professional career in the Dominican Summer League, making 34 errors in 51 games at shortstop for an .863 fielding percentage in 2009, and slowly progressed through the farm system, albeit behind several other top prospects. In 2012, he made 51 errors playing 110 games in the field between second base and shortstop, for the Class A-Advanced Myrtle Beach Pelicans.

Playing for the Double-A Frisco RoughRiders in 2013, he batted .257/.289/.339 with 2 home runs in 389 at bats. Predominantly an infielder in the Rangers’ system, he began playing sporadically in the outfield during the 2014 season, in which he split time between Myrtle Beach and Frisco RoughRiders, winning the Texas League batting title. He also participated in the Venezuelan Winter League, where he earned recognition as the most valuable player (MVP) by posting a .372 batting average with six home runs and a .988 on-base plus slugging (OPS).

Herrera was selected by the Philadelphia Phillies from the Rangers in the 2014 Rule 5 draft, which stipulated that he must remain a part of their roster for the 2015 season. Phillies’ general manager Rubén Amaro, Jr. said that the Phillies viewed Herrera as an intriguing prospect, insofar as he “fits the bill” of what the club sought to do – develop speed and athleticism within their lineup, as well as give younger players a chance to prove themselves. Paula Wolf, a writer for LNP, compared Herrera to another former Phillies’ outfielder selected in the Rule 5 draft, Shane Victorino.

Standing 5 feet 11 inches (1.80 m) tall and weighing 200 pounds (91 kg), entering 2015, he cumulatively hit .294 during his minor league career, with a .354 on-base percentage. Power hitting is not a strength, but the Phillies were optimistic about his potential to develop as a major league hitter. In 2015 scouts called him a line drive hitter with the ability to “use his speed to create havoc.” Some felt he had potential to develop into a base stealer if he could embody a more cerebral approach on the basepaths. Defensively, he spent most of his early minor league career as a second baseman or shortstop before transitioning to the outfield.

In May 2016, Manager Pete Mackanin benched Herrera for not hustling on a ground ball, something he had observed Herrera do before. Herrera would go on to have a breakout season in 2016. On July 5, Herrera was named to the NL All-Star team, the first time in his career. He finished the season batting .286/.361/.420 and 15 home runs and 49 RBIs, and leading the majors in infield hits (30) and leading NL center fielders in errors (9). On December 15, Herrera signed a 5-year, $30.5 million contract extension.

In June 2017, Herrera hit 14 doubles, a Phillies franchise record. In July, following him catching the unfavorable attention of his manager for ignoring signs and taking what his manager felt was a lackadaisical approach to the game, he was benched mid-game by Manager Mackanin for not hustling. He finished the season batting .281/.325/.452 and 14 home runs and 56 RBIs.

On May 7, 2018, Herrera became the fastest player in Phillies history to reach 500 career hits since Chase Utley in 2007. He recorded his 500th hit in his 476th career game. Utley did so in 474 games. On May 20, Herrera’s 45-game on-base streak came to an end with a dropped third strike against the St. Louis Cardinals. It was the fourth-longest on-base streak in Phillies history. From June 17 to June 22, Herrera homered in five consecutive games, tying the Phillies’ franchise record.

Herrera’s 2019 season was short-lived as he played only 39 games batting a career-low .222/.288/.341, with a home run and 16 RBIs in 126 at bats. He had the slowest sprint speed of all major league center fielders, at 26.7 feet/second. On July 6, he was suspended for the rest of the season retroactive to June 24, due to his violating MLB’s Joint Domestic Violence, Sexual Assault and Child Abuse Policy, in a domestic violence incident on May 27.

On May 27, 2019, Herrera was arrested at the Golden Nugget Atlantic City hotel and casino in Atlantic City, New Jersey, after a report of domestic violence. He was charged with simple assault for allegedly assaulting his 20-year-old girlfriend, Melany Martinez-Angulo, who had visible signs of injury on her arms and neck including “handprint markings” and scratches, and released from custody with a summons and a court date. The maximum penalty in New Jersey for simple assault was six months in jail, plus a $1,000 fine. He was placed on administrative leave by MLB the next day. The domestic violence charges were dropped after his girlfriend opted not to testify and proceed with the case.

On January 14, 2020, Herrera was designated for assignment by the Phillies.