Lively was born to Edward and Ginny Lively in Pensacola, Florida.[1][2] He began playing organized baseball at age 4 in the Tee-ball league; he was allowed to join a year early because of his prowess and the fact that his grandfather, Jim Lively, who coached him throughout his childhood, was the league commissioner.[2] He is a graduate of Gulf Breeze High School.[2]
In 2015, Lively went 8–7 with a 4.13 ERA in 25 games with the Double-A Reading Fightin Phils. He began the 2016 season with Reading before being promoted to the Triple-A Lehigh Valley IronPigs. He received the 2016 Paul Owens Award as best pitcher in the Phillies' farm system.[2] The Phillies added him to their 40-man roster after the 2016 season.[11] He was assigned to Lehigh Valley to begin the 2017 season.
On June 3, 2017, Lively made his major league debut with the Philadelphia Phillies against the San Francisco Giants. He allowed one run on four hits and three walks, earning his first major league win.[12] In his June 24 start against the Arizona Diamondbacks, he collected his first major league RBI with a 2-run home run, but gave up 4 earned runs and took the 9–2 loss.[13] He finished his rookie season with a 4–7 record and 4.26 ERA in 15 major league appearances. In 2018, Lively pitched in 5 games for Philadelphia, but after struggling to an 0–2 record and 6.85 ERA, he was designated for assignment on September 3, 2018.[14]
Kansas City Royals
On September 5, 2018, Lively was claimed off waivers by the Kansas City Royals, who then designated Eric Stout for assignment to add Lively to the 40-man roster.[15] Lively recorded a 1.35 ERA in 6.2 innings of work for Kansas City in 2018. He was assigned to the Triple-A Omaha Storm Chasers to begin the 2019 season. Lively himself was designated for assignment on June 20, 2019, following the promotion of Humberto Arteaga. He allowed 3 runs in the only inning he pitched for Kansas City.
Arizona Diamondbacks
On June 22, 2019, Lively was traded to the Arizona Diamondbacks in exchange for cash considerations.[16] He was assigned to the Triple-A Reno Aces, where he recorded a 5.04 ERA and 2–1 record across 7 appearances.
Samsung Lions
On August 7, 2019, Lively left the Diamondbacks organization to sign with the Samsung Lions of the KBO League. Lively pitched to a 4–4 record and a 3.95 ERA in his first season with Samsung. Lively re-signed with Samsung for the 2020 season on a $700,000 contract.[17] In 2020 he pitched to a 6–7 record and 4.26 ERA in 21 appearances. Lively only made six appearances in 2021, registering a 4.05 ERA. On June 1, 2021, Lively was released after being diagnosed with a shoulder injury.[18]
Cincinnati Reds (second stint)
On January 6, 2022, Lively signed a minor league contract with the Cincinnati Reds.[19] He spent the entire year with the Triple-A Louisville Bats, making 18 starts and registering a 2–5 record and 4.09 ERA with 79 strikeouts in 77.0 innings pitched. He elected free agency following the season on November 10.[20]
On November 19, 2022, Lively re-signed with the Reds on a new minor league contract. He was assigned to Triple-A Louisville to begin the 2023 season, where he posted a 4–0 record and 2.33 ERA with 16 strikeouts across 5 games (4 starts). On May 9, 2023, Lively had his contract selected to the active roster.[21] He made his first start on May 20 against the New York Yankees, allowing 2 runs on 2 hits and one walk with a career-high 8 strikeouts in 5.2 innings pitched.[22] In an August 1 start against the Chicago Cubs, Lively allowed 13 runs on 13 hits and 2 walks in 4.0 innings of work.[23] In 19 total games (12 starts) for Cincinnati, he logged a 4–7 record and 5.38 ERA with 79 strikeouts in 88+2⁄3 innings of work. Following the season on October 18, Lively was removed from the 40–man roster and sent outright to Triple–A Louisville.[24] He elected free agency on November 6.[25]
Cleveland Guardians
On December 12, 2023, Lively signed a major league contract with the Cleveland Guardians.[26]