But Maddon doesn't want his players to lose sight of what made them so special last year.
"More than anything, we have not been really relishing in victory, and I think we've been too painful in defeat," Maddon said on Tuesday night.
"We got to the World Series last year by kind of being free-spirited about the whole thing and permitting ourselves to go out there and play openly with risk taking and not worrying and all that kind of stuff."
But it isn't easy for these Rays to revert to that style.
The lovable underdog label doesn't sell as easily after a deep postseason run. Although essentially eight of last year's nine regulars remain on the team, their expectations are different.
"The fact of the matter is, we've experienced winning, and we don't want to go back to that old team," third baseman Evan Longoria said. "We don't want to concede to the fact that last year was fun. We want to continue that. We have the same talent, if not more talent, this year than we had last year. So I think it's a big disappointment for us to lose games."
Another reason for last season's team being more relaxed was the fact it was ahead. With Tuesday's win, Tampa Bay (64-54) is three games back of the AL Wild Card leaders and 10 games behind the Yankees in the AL East.
Through 118 games last year, the Rays' record was seven games better and they were three games up in the division.
"It feels like we're going to be disappointed if we have a winning record but don't make the playoffs, and that wasn't the case last year," second baseman Ben Zobrist said. "It was like, 'Even if we just have a winning record, we've far exceeded the expectation.' It's kind of like you can never have the same feeling you had last year, when there was absolutely nothing to lose."
The division-rival Yankees and Red Sox boast teams chocked full of veterans who are used to the pressures of winning. The Rays, however, sport a rather young team, and this is the first time this franchise is somewhat expected to win.
But Maddon and his new head of hair are here to help ease some of that tension.
"I think that once you've been to the World Series as young as we have, you want to live up to all these expectations," Maddon said. "And I would think that, for the most part, I would bet that our guys feel that they're letting people down when they're not performing as they're capable of. I think when you do go in that direction, losses can be painful, and you don't really revel in the joy of the day as much. But I want us to get back to that."