Wine was sent to the expansion Montreal Expos at the end of spring training in 1969 as compension for pitcher Larry Jackson, who had been selected from the Phillies in the 1969 expansion draft but chose to retire rather than join the Expos. At first he was the back-up to Maury Wills, but he took over when Wills was traded to the Los Angeles Dodgers in June 1969. Although he played in just 121 games, Wine led the league in errors with 31, and batted just .200.