A look into Stan Bowman’s depth moves that helped in his last Stanley Cup championship

Additionally, Darling appeared in five playoff games in 2015 and earned his first postseason win in Game 1 of the first round against the Nashville Predators. The Blackhawks fell behind 3–0 before Darling replaced Corey Crawford, and Chicago rallied for a 4–3 double-overtime victory, which head coach Joel Quenneville called ‘one of the greatest relief performances you’re going to see.’ All in all, he won three playoff games and posted a 2.28 GAA and .936 SV%, contributing to Chicago’s Cup win that season. As well, Darling became the first Illinois-born player to win the Stanley Cup with the Blackhawks, and his signing was a slam dunk for Bowman.

Bowman Signed Brad Richards to a One-Year Deal

The New York Rangers had just bought out the remaining seven years of veteran Brad Richards’ contract in June 2014, and Bowman made a low-risk move by signing the centerman to a one-year, $2 million deal on July 1, 2014.

Richards posted 37 points (12 goals, 25 assists) in 76 regular-season games with the Blackhawks and made an impact in the playoffs as well, serving as the team’s second-line center, mostly playing between Patrick Kane and Bryan Bickell and tallying 14 points (3 goals, 11 assists) in 23 postseason games. Moreover, he saved some of his best work for Game 6 of the Finals against his former team, the Tampa Bay Lightning.

Richards assisted on the only two goals scored in Game 6 of the Finals, including a spectacular helper with just over five minutes remaining. He froze the opposition with a faked shot before sliding the puck over to Kane, who buried the one-timer to give the Blackhawks the insurance marker and seal the 2–0 Game 6 win to capture the Cup.

Richards’ veteran presence and timely contributions helped push the Blackhawks over the top, making Bowman’s one-year gamble on him a vital piece in winning another championship.

Bowman Traded for Kimmo Timonen

At the 2015 NHL Trade Deadline, Bowman made an intriguing move by acquiring veteran D-man Kimmo Timonen from the Philadelphia Flyers in exchange for a second-round draft pick and a conditional fourth-round pick. At 39 years old and recovering from blood clots that nearly ended his career, Timonen hadn’t played a single game that season before the trade, but Bowman saw value in the blueliner’s experience and leadership.

Timonen played in 16 regular-season games down the playoff stretch, averaging just under 12 minutes a night, and he also appeared in 18 postseason games, mainly in a third-pairing role, averaging just under nine minutes a night.

While Timonen didn’t exactly light up the scoresheet, finishing without a point, his steady veteran presence on the blue line and inspirational leadership in the locker room made a difference after returning from nearly a full season off due to a blood clot. After the Blackhawks’ Game 6 win over the Lightning in the Finals, captain Jonathan Toews accepted the Stanley Cup from commissioner Gary Bettman and handed it to Timonen, who finally got the chance to hoist Lord Stanley before retiring after the season and going out as a champion.

Bowman Traded a First-Round Pick for Antoine Vermette, Who Scored Three Game-Winners

Just days before the 2015 NHL trade deadline, Bowman made a bold move, trading the Blackhawks’ 2015 first-round pick and a prospect to the Arizona Coyotes in exchange for forward Antoine Vermette, a veteran two-way center who had recorded 35 points in 63 games with Arizona before the trade.

However, the centerman had a tough time finding his rhythm in the final 19 games of the 2014-15 regular season, tallying only three assists. That said, despite early doubts, he stepped up in the playoffs, scoring three clutch game-winners during the Blackhawks’ 2015 Stanley Cup run.

His first came in overtime of Game 4 against the Anaheim Ducks in the second round, tying the series 2-2. He followed that by scoring late in Game 1 of the Final, giving Chicago a key road win over Tampa Bay. His final game-winner came in Game 5 against the Lightning, and his three clutch tallies turned Bowman’s deal from a potential flop into a huge success, as Vermette became a major factor in the 2015 Cup win.

This time around, heading into the 2025–26 campaign with the Oilers, Bowman already has his veteran core intact, much like he did with his Blackhawks team almost a decade ago. However, while his last Cup win saw him prioritize adding experience, this time he appears to be shifting toward youth, with players like Matt Savoie and Isaac Howard looking to crack Edmonton’s lineup next season.

For now, it’s a contrast to the approach he took nearly a decade ago, but the fact remains, Bowman found the missing pieces to win the Cup once before. And who knows, there’s still a long way to go before the 2026 playoffs. While he’s focused on getting younger now, that priority could shift by the time the trade deadline rolls around.