The Five: Red Wings Worst UFA Contracts

When it comes to contracts given by the team to unrestricted free agents, the Detroit Red Wings fanbase isn’t shy about giving their opinion. And for the most part, they don’t tend to like many of the signings.

People are unhappy with the term given to the likes of Ben Chiarot, Andrew Copp and J.T. Compher. They certainly don’t like anything at all about the pact given to Justin Holl.  Some even suggest the Holl contract to be among the worst ever in team history.

Making the decision to assess the team history with UFAs, Detroit Hockey Now is presenting our opinion on the five worst UFA contracts in Red Wings history. Did Holl make the cut? Read on and find out.

This Red Wings Choice Wasn’t A Weiss Decision

When Valtteri Filppula left the Red Wings for Tampa Bay, then-Detroit coach Mike Babcock was pushing hard for the team to sign UFA center Stephen Weiss of the Florida Panthers. The team ending up giving Weiss a five-year deal with $24.5 million, with an AAV of $4.9 million.

However, a chronic core issue that led to sports hernia surgery would slow Weiss. Over two seasons, he would account for 11 goals and 18 assists in 78 games before he was bought out in 2015.

Hatcher Didn’t Hatch In Detroit

Adding all-star Derian Hatcher in 2003 to a defense that already was including future Hall of Famers Nicklas Lidstrom and Chris Chelios seemed to be a stroke of genius for Red Wings GM Ken Holland. Instead, the move struck out.

Just 15 games into his Red Wings career, Hatcher would suffer a significant knee surgery requiring surgery. When clubs were coming back from the 2004-05 lockout season, Detroit was opting to utilize a compliance buyout to rid themselves of the remainder of Hatcher’s five-year $30-million contract.

CuJo? How About Oh No

With Dominik Hasek’s retirement following the 2001-02 Cup win, Detroit was in need of a netminder. The choice was between two all-star UFAs – Ed Belfour and Curtis Joseph. The Red Wings would opt for the latter, giving Joseph a three-year, $24-million contract. They’d soon come to regret their decision.

Curtis Joseph Detroit Red Wings Upper Deck Victory Card @DetroitRedWings #LGRW #NHL pic.twitter.com/WVxLN2fIR9

— NHL Hockey Cards (@NHLHockeyCards) September 18, 2023

While his numbers were solid in Detroit, Joseph never gave off the impression he really wanted to be with the Red Wings. When he and his family were arriving to the press conference announcing his signing, they marched in like a funeral procession. Joseph happily allowed backup Manny Legace to start the first time the Wings would visit his previous home to play the Toronto Maple Leafs. By contrast, the previous year, Hasek demanded he play in Buffalo against his old club the Sabres. He didn’t want it to be viewed as if he was ducking the assignment.

Had the club been satisfied with Joseph’s performance, there’s no way they would’ve brought Hasek back out of retirement and to Detroit the following season. His arrival would create a soap-opera like environment in the dressing room between the two netminders.

A Signing That Went To The Dogs

Losing Vladimir Konstantinov to a debilitating brain injury suffered in a limousine crash days after their 1996-97 Stanley Cup win, the Red Wings were left with a gaping hole on their defense. Reaching out to sign Uwe Krupp to a four-year, $16.4-million contract was a double whammy, It was not only going to fix their defense, Detroit would pluck Krupp off the roster of their arch rivals, the Colorado Avalanche.

Uwe Krupp! 🚨 #LGRW | @DetroitRedWings | #Krupp pic.twitter.com/s7GegrnyRT

— NHL Deutsch (@NHLde) August 10, 2024

Krupp scored the Cup-winning goal for the Avs in 1996. But he’d play only 30 games for the Red Wings. A herniated disc put him out 22 games into the 1997-98 season. Krupp would miss the entire 1999-2000 and 2000-01 campaigns.

Making matters worse, it came to light that Krupp was partaking in his hobby of dog sled racing while out of action. The Wings would suspend Krupp. He’d counter by filing a grievance over the $12.3 million he was owed by the team. Eventually, they were able to resolve their differences. Krupp would return to play eight games in 2001-02.

Red Wings Young And Useless

Adding a 40-goal scorer to the lineup is always cause for excitement. And that level of excitement was palpable when the Red Wings were scooping up Warren Young. Playing on Mario Lemieux’s wing, he was a 40-goal sniper in 1984-85 for the Pittsburgh Penguins. He’d agree to a four-year, $1.2 million contract with Detroit.

Young’s numbers weren’t dismal. He’d score 22 goals for the 1985-86 Wings. But 22 is a long way from 40. After one season, the Red Wings let him go. By 1988, Young was completely out of hockey.