The 1965 season and the move to Moorabbin was a huge success. Starting with more than 51 000 at the opening game, the Saints packed them in at their new home. In Round 9, in front of more than 72 000 at the MCG, St Kilda seized top place from Melbourne with a big win, then held on for the remainder of the season to win the minor premiership for the first time. The momentum continued; two days after the last game, Stewart was a surprise winner of the game's highest award, the Brownlow medal. He had tied with North Melbourne's Noel Teasdale, but the medal went to Stewart on a countback (Teasdale received a retrospective award 24 years later). Then St Kilda won into the Grand Final in a thrilling semi-final against Collingwood decided by only one point. The medal win did not deflect Stewart's concentration – he dominated. His team were into only their second Grand Final, the first for 52 years. As St Kilda had not won a single premiership in its 93-year existence, it looked like history in the making. Essendon surprised by also beating Collingwood to advance to the Grand Final. Anticipation got to the inexperienced St Kilda players and coach; they got a bit too "up", overtrained during the week and were floundering come the big day. The Bombers, finals veterans, made them pay dearly and had the game won by three quarter time. Stewart went down fighting and was named his team's best player. He had shown a distinct liking for the big game during his finals performances. The following season, the Saints jumped out of the blocks and after winning the first eight games there was speculation that they could go through undefeated. Naturally, talk like that precipitated a slump, and by the last game, they were in danger of sliding right out of the finals if they lost. Thanks to Baldock, the Saints pulled a tight game out of the fire and went into the finals as equal favourites for the flag. Back in the 1960s, the Brownlow vote count was broadcast live on radio on the Monday following the end of the home-and-away season. As the reigning Brownlow medallist, Stewart thought he would only poll 14 or 15 votes, adding that he felt his last three or four games of the season had been poor. But by the end of the broadcast, Stewart had won his second successive Brownlow with 21 votes, winning by four from Carlton star John Nicholls, the first player to win back-to-back Brownlows since Dick Reynolds in 1937 and 1938.