In 16 seasons as general manager, Holland has guided the Detroit Red Wings to three Stanley Cup championships and has reached the playoffs every season, extending Detroit’s postseason steak to 23 consecutive--the longest active streak in North American professional sports.
Holland, who’s been with the organization for over 30 years, took over a Red Wings team coming off its first Stanley Cup in 42 years and molded it into one of the most consistent franchises of all-time.
Since Holland became GM in 1997-98, the Red Wings have 861 victories, including regular season and playoffs--the most of any NHL franchise--and Detroit has won four Presidents’ Trophies and 10 Western Conference Central Division titles.
The Red Wings success would not have been possible if Holland hadn’t made some key acquisitions in free agency, carefully assembling a championship-caliber puzzle year after year.
With NHL free agency beginning on July 1, let’s take a look back at five of the biggest free-agency acquisitions during the Holland era:
Luc Robitaille—July 5, 2001
Los Angeles Kings forward Luc Robitaille was a big reason why Detroit’s Stanley Cup hopes were crushed in 2001.
With four points from Robitaille in the first-round series, the seven-seed Kings pulled off a monumental upset, eliminating the heavily-favored Wings from the 2001 playoffs. That offseason, when Robitaille received a less-than-adequate offer from the Kings, Holland came calling.
Robitaille, who played 12 of his first 15 NHL seasons in LA, signed a two-year contract with Detroit for $9 million--considerably less than market value at the time.
He compiled 50 points on 30 goals and 20 assists in his first season with the Red Wings, and added nine points in the 2002 playoffs to help Detroit win its third Stanley Cup in six years. After 16 NHL seasons, Robitaille hoisted the Cup for the first time.
Robitaille played one more season with the Wings, posting 31 points in 81 games. In 2003, he returned to LA for his last two NHL seasons and retired as the highest-scoring left winger in league history.
Brett Hull—August 22, 2001
Over the course of his career as Red Wings GM, Holland has made a habit of making impactful late-summer acquisitions.
The addition of Brett Hull in 2001 was no different.
After three seasons with the Dallas Stars, including scoring the series-clinching goal in the 1999 Stanley Cup finals, Hull found himself without a team. The Stars declined their option on Hull’s contract but in August 2001, at age 37, the all-star forward wasn’t prepared for retirement.
That summer, The Wings had already traded for Dominik Hasek and signed Robitaille, appearing to be a complete team ready for another run at the Stanley Cup.
But after Red Wings veterans lobbied for Holland to sign Hull, Detroit came to terms with one of the most prolific scorers in history when he signed a two-year, $9 million deal.
In 2001-02, Hull posted 63 points for Detroit, playing in all 82 regular season games for the first time in his NHL career.
He also tallied 18 points in the playoffs, including two goals in the 2002 finals to help the Red Wings capture the franchise’s 10th Stanley Cup.
Hull posted 144 points over the next two seasons with the Wings to help extend Detroit’s postseason streak. He signed a free-agent contract with the Phoenix Coyotes in 2004 before the NHL lockout and played just five games for the Coyotes before retiring in 2005.
Chris Osgood—August 8, 2005
Goalie Chris Osgood was drafted by Detroit in 1991 and spent his first eight NHL seasons with Detroit.
But in 2001 when the Red Wings acquired Dominik Hasek, Osgood was placed on waivers. After spending four seasons with the New York Islanders and St. Louis Blues, Osgood reunited with the Wings in 2005.
In another late-summer acquisition by Holland, Osgood, at 32 years old, signed a one-year, $900,000 deal to return to Detroit. But this time, he was competing with Manny Legace for the starting spot on first-year coach Mike Babcock’s team.
In his first season back with Detroit, Osgood went 20-6-5 in sporadic duty and the top-seeded Red Wings were upset by the Edmonton Oilers in the first round of the playoffs.
Osgood signed on for five more seasons in Detroit, and in 2007-08, he won back the starting job and led the NHL with a 2.09 goals-against average. However, Hasek, who re-signed with Detroit in 2006-07, was given the starting job in the 2008 playoffs.
Osgood replaced Hasek between the pipes in Game 4 of the first round and put together a streak of nine consecutive victories. He went 14-4 in the 2008 playoffs with a 1.55 GAA, leading Detroit to the Stanley Cup championship—the second Cup of his career.
Osgood played 80 games throughout the next three seasons, compiling a 38-21-14 record, but after sports hernia surgery in 2011, he retired that offseason at age 38.
Brian Rafalski—July 1, 2007
On July 1, 2007, when Mathieu Schneider left the Red Wings to join the Anaheim Ducks, it looked like Detroit’s blue line was in trouble.
But the same day that the talented two-way defenseman departed for Anaheim, Holland signed defenseman Brian Rafalski to a five-year, $30 million deal, and the panic would eventually dissipate.
Rafalski was a hometown player from Dearborn, Mich. who instantly fit in with Detroit's system and locker room, and, paired with Nicklas Lidstrom, proved to be a crucial asset on a lethal power-play blue line.
Rafalski posted 42 assists and added 13 goals, including 10 power play goals in 2007-08, his first season with Detroit. He earned a plus-27 rating in the regular season, leading the Wings to a 51-win campaign and 116 points—the club’s highest output since 1997-98.
The defenseman earned 14 points during the 2008 playoffs to help the Wings secure their first Stanley Cup since 2002.
Rafalski played three more seasons for the Red Wings, compiling 204 points in his four seasons with Detroit, but after battling debilitating injuries in 2010-11, Rafalski unexpectedly retired at age 37 with one year left on his contract.
Marian Hossa—July 2, 2008
Forward Marian Hossa was moved from the Atlanta Thrashers to the Pittsburgh Penguins at the 2008 trade deadline and was the highest-touted free agent on the market that offseason.
After defeating Hossa and the Penguins in the 2008 Stanley Cup finals, the Red Wings signed Hossa to a one-year, $7.45 million contract.
In his only season with the Red Wings, Hossa scored 40 goals and added 31 assists, helping Detroit return to the Stanley Cup finals for the second consecutive year.
Hossa posted 15 points in the playoffs, but the Red Wings fell just short of winning back-to-back Stanley Cup championships, losing to the Penguins in a heartbreaking seven-game series.
Following the 2008-09 season, after failing to come to terms with Detroit, Hossa cashed in for the long haul, inking a 12-year deal with the Chicago Blackhawks for $62.8 million.
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