In 2022, Shackil joined WFAN and substituted for John Sterling as the play-by-play announcer for the New York Yankees when Sterling was absent.[2] WFAN named Shackil as Sterling's permanent substitute before the 2023 season.[6] He also became host of the WFAN post-game show.[7] Shackil also fills in on the YES Network and co-hosts a podcast with David Cone on Jomboy Media.[2] While filling in for Sterling on June 28, 2023, Shackil called Domingo Germán's perfect game.[8]
Following Sterling's retirement in April 2024, Shackil and Emmanuel Berbari assumed play-by-play duties for the Yankees for the remainder of the season.[9] After the Yankees hired Dave Sims to succeed Sterling for the 2025 season, Shackil announced that he was stepping away from WFAN's postgame show to focus on television broadcasting.[10] Shackil debuted as a lead play-by-play broadcaster for the YES Network when he called a series between the New York Yankees and the Athletics in May 2025.[11]