He was on the ice in Philadelphia in 2010 when the Blackhawks won their first Cup since 1961 thanks to Patrick Kane's overtime winner.
But Ladd was part of a post-Cup salary dump by the Blackhawks and ended up in Atlanta, then moved with the franchise to Winnipeg after the 2010-11 season.
This spring he helped guide the Jets to their first playoff berth since the NHL moved back to the hockey-mad prairie town. But they were swept by the Anaheim Ducks in the first round, and Ladd was forced to watch his old friends celebrate a little more than a week ago after besting the Tampa Bay Lightning in an emotional six-game series.
"Obviously happy for them, but ...," said Ladd, who is nominated for the King Clancy Award for dedication to the game on and off the ice, pausing before finding the appropriate words to describe watching another team win the ultimate hockey trophy.
"Definitely irks you a little bit because you want to be the guy doing the same thing. I know they’re a great group of guys from their trainers, through management and obviously the guys in that room that I know, so, happy for them."
The Maple Ridge, British Columbia, native is the owner of two Stanley Cup rings, having won a Cup as a young player with the Carolina Hurricanes in 2006. Four years later, he was part of a Blackhawks team that had scratched and clawed its way from irrelevance to a championship, so he understands that there are certain growing pains that are, like it or not, part of evolving as a franchise.
So is it true that to win you have to first lose? And is that the arc the Jets are now on?
"I think you’d like to say no," Ladd said. "But every experience I’ve had says contrary. Whether it was in Chicago, Detroit taught us a few lessons before we took that next step. So yeah, I think the biggest thing I think you learn is there’s such a fine line between winning and losing and you have to find those little things that will get you over the hump."
In each of the Jets' four games this spring they held leads over Anaheim but could not find a way to close the deal.
"Our series this year was extremely close," Ladd said. "Those four games could have gone either way except maybe the Game 4. It was just finding those ways to win. Definitely some big learning experiences for us and a lot of guys that hadn’t had the opportunity to play playoff hockey and something that’ll help them along the way."
The Jets continue to evolve as a team, adding Drew Stafford and defenseman Tyler Myers shortly before the trade deadline in exchange for disgruntled forward Evander Kane and defenseman Zach Bogosian. They have top-end talent on the blue line in Jacob Trouba and top defensive prospect Josh Morrissey, promising skill up front in the form of Nikolaj Ehlers and Nicolas Petan and a promising young netminder in Connor Hellebuyck. But Ladd knows that it’s the Jets’ work ethic that was a catalyst to making the playoffs and nothing can be taken for granted.
"I’d say we had a group that understood what we needed to do to be successful. Paul [Maurice, head coach] did a great job of laying that out," Ladd said. "And we came to work every day to reach that goal."
And there’s no question the fans in Winnipeg are expecting more after a brief but emotional return to the postseason.
"Just the excitement level around town," Ladd said. "Where everywhere you went people were wearing Jets stuff and talking about the playoffs. I think you feel that as a player and, like I said, a lot of those guys hadn’t experienced that before, and you have to experience that to give you that extra drive to make sure you want to get back there."
Finally, it would not be a chat with Ladd if we didn’t ask the former Atlanta resident about the weather in Winnipeg.
Is it really a dry cold?
"Every time I talk to you, I get this question," Ladd noted. "It is [a dry cold]. I don’t know, man. Minus-30 is minus-30. I’ve never seen a warm minus-30. But it’s warm in the rink."