In January 1927, the White Sox traded Grabowski to the New York Yankees. He had his best season for the 1927 "Murderer's Row" New York Yankees, considered by some to be the best baseball team in history. Grabowski appeared in 70 games for the 1927 Yankees, sharing the catching duty with Pat Collins and Benny Bengough in 1927. Grabowski had a .350 on-base percentage for the 1927 Yankees. He remained with the Yankees through the 1929 season and won two World Series championships with the Yankees in 1927 and 1928.