Draft and minor leagues

Strickland was drafted by the Boston Red Sox in the 18th round, 564th overall pick, of the 2007 Major League Baseball draft. He made his professional debut with the GCL Red Sox, logging a 6.04 ERA in 9 appearances. The next year, he played for the Low-A Lowell Spinners, and pitched to a 5-3 record and 3.18 ERA in 15 games. He was assigned to the Single-A Greenville Drive to begin the 2009 season, and posted a 5-4 record and 3.35 ERA in 83.1 innings of work.^[2]

On July 22, 2009, Strickland was traded to the Pittsburgh Pirates along with Argenis Díaz in exchange for Adam LaRoche.^[3] He finished the year with the Single-A West Virginia Power, registering a 4-2 record and 3.77 ERA in 8 games. He split the 2010 season between West Virginia and the High-A Bradenton Marauders, accumulating a 2-5 record and 5.53 ERA with 25 strikeouts.^[4] However, his season was cut short due to a right elbow strain. He missed the entire 2011 season with a rotator cuff injury that required surgery.^[5] In 2012, he split the year between the Double-A Altoona Curve and Bradenton, logging a 4-4 record and 3.70 ERA with 58 strikeouts in 33 appearances. On November 20, 2012, the Pirates added Strickland to the 40-man roster to protect him from the Rule 5 draft.^[6] On March 27, 2013, Strickland was designated for assignment by the Pirates.^[7]

On April 2, 2013, Strickland was claimed off waivers by the San Francisco Giants.^[8][9] Strickland underwent Tommy John surgery in May and was designated for assignment on July 23, 2013, and released the next day, but re-signed on a minor league contract with the Giants 5 days later.^[10] He was re-added to the Giants' 40-man roster on November 20, 2013.^[11]

San Francisco Giants (2014–2018)

Seattle Mariners (2019)

On January 24, 2019, Strickland signed a one-year deal with the Seattle Mariners.^[29] On March 30, Strickland suffered a Grade 2 right lat strain, which put him out for a couple of months.^[30]

Washington Nationals (2019)

On July 31, 2019, the Mariners traded Strickland and Roenis Elías to the Washington Nationals in exchange for Aaron Fletcher, Taylor Guilbeau, and Elvis Alvarado.^[31] In 24 games with the Nationals, Strickland went 2-0 with a 5.14 ERA. Overall in 2019, combined with both teams, Strickland made 28 total relief appearances with a 2-1 record and a 5.55 ERA. The Nationals finished the 2019 year with a 93-69 record, clinching a wild card spot, and eventually went on to win the 2019 World Series over the Houston Astros, their first championship in franchise history. It was also the second time Strickland won a World Series in his career.^[32] During the NLDS against the Los Angeles Dodgers, he gave up his 9th career postseason home run, a record for relief pitchers. He was released by the Nationals on March 14, 2020.^[33]

New York Mets (2020)

On June 29, 2020, Strickland signed a minor league contract with the New York Mets organization. On July 23, it was announced that Strickland had made the Opening Day roster for the Mets. On July 30, Strickland was designated for assignment when Brian Dozier was added to the roster. He was outrighted on August 2. On August 31, 2020, Strickland was selected back to the active roster.^[34] Strickland's contract was selected on August 31 adding him to the active roster. That night he threw a scoreless inning of relief with two strikeouts, but was designated for assignment again the next day.^[35] Strickland elected free agency on October 15, 2020.

Tampa Bay Rays (2021)

On February 2, 2021, Strickland signed a minor league contract with the Tampa Bay Rays organization.^[36] On April 9, 2021, Strickland was selected to the 40-man roster.^[37] In 13 games for Tampa Bay, Strickland recorded a 1.69 ERA.

Los Angeles Angels (2021)

On May 15, 2021, Strickland was traded to the Los Angeles Angels in exchange for cash considerations or a player to be named later.^[38] In 9 appearances for the Angels, Strickland struggled to a 9.95 ERA before being designated for assignment on June 7.^[39]

Milwaukee Brewers (2021)

On June 12, 2021, Strickland was traded to the Milwaukee Brewers in exchange for cash considerations.^[40]

Cincinnati Reds (2022)

On March 23, 2022, Strickland signed a one-year contract with the Cincinnati Reds.^[41] He made 66 appearances for Cincinnati in 2022, pitching to a 3-3 record and 4.91 ERA with 60 strikeouts and 7 saves in 62.1 innings of work.

On February 18, 2023, Strickland re-signed with the Reds on a minor league contract.^[42] Strickland was released by the organization on March 25.^[43] He re-signed with the Reds on a new minor league contract on March 27.^[44] In 12 appearances for the Triple-A Louisville Bats, Strickland struggled immensely to the tune of a 11.45 ERA with 8 strikeouts in 11.0 innings pitched. He was released by the Reds organization on May 9.^[45]

Los Angeles Angels (second stint)

On February 16, 2024, Strickland signed a minor league contract with the Angels.^[46] On April 8, after two games for the Triple–A Salt Lake Bees, his contract was selected to the major league roster.^[47]