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Dylan Larkin trade request tests Steve Yzerman, but Red Wings GM has been here before

General manager Steve Yzerman’s captain put him in a bind. The face of his franchise requested a trade, and the saga was unfolding in public.

But this was long before Detroit Red Wings center Dylan Larkin’s trade request sent shock waves around the NHL last week.

It was 2014, and Yzerman’s captain at the time was Martin St. Louis — a Hall of Fame player and the Montreal Canadiens’ current coach, but at the time the leading scorer for the Tampa Bay Lightning.

So, as challenging as the Larkin trade request could be for Yzerman this summer, this is also not an unfamiliar situation for the Red Wings GM to navigate. He’s not one to get rattled or pushed into a corner.

Back then, Yzerman executed a strong deal to resolve St. Louis’ trade request — plus another one two years later involving Jonathan Drouin.

Larkin may have given Yzerman a short list of preferred destinations, including the Minnesota Wild, league sources told The Athletic. But Yzerman still has some agency in how to proceed with Larkin, who has five years left on his deal, despite his no-trade clause.

“Steve Yzerman owes one thing to the Detroit Red Wings only, and (that’s) what’s best for them,” former NHL GM Craig Button said. “Dylan Larkin can’t sing and whistle at the same time. He can’t sit down and say, ‘I have a no-(trade) clause to protect me from you trading me anywhere,’ and then you coming back and saying, ‘I don’t want to play here anymore.’ You don’t get to pick.

“I don’t care about the list you gave me. You said, ‘I want to be traded,’ I’ll determine where we trade you. … And if you don’t like it, you have a contract, you play.”

That’s one possible tactic. Here’s what Yzerman’s history tells us about how he could handle this situation.

In 2014, Martin St. Louis, by that point captain of the Tampa Bay Lightning, wanted to be traded to the New York Rangers. Steve Yzerman made the best of the situation. (Mike Carlson / Getty Images)

Martin St. Louis

The situation

St. Louis is one of the Lightning’s all-time greats. He was their first Hart Trophy winner and led them to their first Stanley Cup title in 2004. By the 2013-14 season, St. Louis was 38 years old, but still playing at a high level, scoring 30 goals that season.

He had just been named captain in October 2013, replacing another face of the franchise in Vincent Lecavalier, who had been bought out. And the Lightning were having a good season, preparing for a playoff push.

That all made the situation even more challenging for the Lightning when Yzerman — also the executive director for Team Canada — left St. Louis off of the initial Olympic team roster that winter in Sochi, Russia.

St. Louis was very upset over the snub, especially coming from his own GM, and met privately with Yzerman before the February Olympics to request a trade. St. Louis had a full no-movement clause and made it clear his preferred landing spot was with the New York Rangers, with his family having an offseason home in Greenwich, Conn.

The timeline

St. Louis’ request came before the February Olympics, with the NHL trade deadline rapidly approaching in early March. It was a tough scenario for the Lightning, as a lot of the young players, including Steven Stamkos, revered St. Louis.

St. Louis still had one year left on his contract. So, Tampa Bay could have tried to delay the decision, but St. Louis’ feelings didn’t change even after he was added to the Olympic team as an injury replacement and won a gold medal.

Yzerman executed the trade with the Rangers on Mar. 5.

The result

Considering Yzerman really had only the Rangers to deal with, he pulled off a very strong deal for Tampa Bay.

The Lightning traded St. Louis to New York for Rangers captain Ryan Callahan, a first-round pick in 2015 and a conditional second-round pick in 2014. Because the Rangers reached the conference final that season, the 2014 second-round pick became a first-round pick. And since the Lightning ended up re-signing Callahan, a condition triggered that sent the Rangers a second-round pick in 2015, and Tampa Bay got an additional seventh-rounder in 2015.

The fact that Yzerman got Callahan plus what turned into a couple of first-round picks should be considered a strong return based on both St. Louis’ requested destination and the timeline. The Rangers went on to the Stanley Cup Final in 2014, losing to the Kings. He played one more season before retiring.

Callahan re-signed in the summer of 2014 on a six-year deal and played five full seasons with Tampa Bay. He was a key leader and role player on teams that went to the Stanley Cup Final in 2015 and the conference finals in 2016 and 2018.

St. Louis addressed fans’ reaction to his request on a media call before the Lightning retired his jersey after his career ended.

“In life, you make decisions, you know? Sometimes you make hard ones,” St. Louis, who retired after the 2014-15 season, said in 2016. “For me, I hope they remember me for what I brought to the team. I came in 2000 to a last-place team. I think I left that team in way better shape than when I came.

“It would have probably been a better story if I had finished my career there, but there are a lot of variables that come along the way as you get older. You have kids … I don’t want to go back into it, you know? Things happen sometimes, and you have to make tough decisions. … So I (wish) they can forgive me, I guess, in that sense?

“I understand their pain. It wasn’t easy for me to do that either. I love Tampa. I loved playing there. I loved everything about it. It was just time to move on, for a bigger reason than just me.”

What we learned

In this particular case, Yzerman did send St. Louis to his preferred destination, the Rangers, though he wouldn’t have done so had he not received a strong return.

Yzerman demonstrated he could net a good deal despite the perceived very few options. And, keep in mind, this trade came before the Lightning’s string of deep runs into the playoffs, though they had been to the conference final in 2011. Yzerman had also just parted ways with another of the best players the franchise had ever had, buying out Lecavalier.

There was certainly a strained relationship between Yzerman and St. Louis, and there has likewise been friction between Larkin and the Red Wings’ Hall of Fame former captain. But where Yzerman’s team is now in its arc is different than with Tampa. That brings added scrutiny to the Red Wings, who are a decade removed from their last playoff berth.

This scenario also revealed that fans can be forgiving of their former stars. It wasn’t that way immediately for St. Louis, as there was plenty of bitterness from fans. It took several years for the fences to mend. But you couldn’t tell there were any issues at all when St. Louis got his jersey finally hoisted to the rafters in January 2017.

In 2016, Jonathan Drouin wanted to be traded. After being demoted to the AHL, he held himself out of the lineup. Steve Yzerman suspended him without pay, then brought him back for the Lightning’s playoff run, which dramatically changed the dynamic. (Mike Stobe / Getty Images)

Jonathan Drouin

The situation

Drouin was a prized Lightning prospect, the No. 3 pick in the 2013 NHL Draft. But the talented winger struggled to find consistent playing time with the Lightning (including getting healthy scratched in all but six playoff games in their 2015 run to the Cup Final).

After Drouin was demoted to AHL Syracuse in January 2016, his agent, Allan Walsh, released a statement to make his November 2015 trade request public, calling it an “untenable” situation. Drouin started a holdout, not playing for Syracuse, and Yzerman suspended him without pay.

The timeline

The trade request was initially made privately between Walsh and Yzerman in November 2015, then put in public view in January in Walsh’s statement.

Drouin ended his holdout in March and reported to AHL Syracuse, preparing for a playoff push. Drouin was brought up to Tampa Bay for the Stanley Cup playoffs and played a big role in the Lightning’s run to the Eastern Conference final. He had 14 points in 17 playoff games. In June, after the season, Drouin rescinded the trade request, hoping to stay with the team.

The result

The Lightning did end up trading Drouin in June 2017 in a big swap for defenseman Mikhail Sergachev. The teams also traded conditional 2018 draft picks (Tampa received a second-round pick, and Montreal received a sixth-round pick).

The trade wasn’t necessarily made because of the then-rescinded trade request but because the Lightning really liked Sergachev, who became a key cog on Tampa’s back-to-back Stanley Cup runs in 2020 and 2021. The Canadiens wanted another star up front, and Drouin was appealing because he is French Canadian.

What we learned

These processes can sometimes be long and evolving.

Drouin’s request came in November 2015, and Yzerman didn’t simply cave. Walsh put out the public statement a few months later to ramp up pressure, especially when Drouin got sent down to the AHL. But Yzerman held firm, suspending Drouin without pay and letting the extremely competitive prospect decide how long he was comfortable holding out.

Drouin blinked first, ending his holdout in March and playing for Syracuse. He was great during the Lightning’s playoff run, which changed the narrative a bit. Teammates supported Drouin, believing in his talent. The sides appeared to mend fences that summer, with Drouin rescinding his request and planning to play a strong role for the team the following season.

Obviously, playing hardball with a touted rookie prospect is one thing compared to an established captain such as Larkin. It would be challenging and awkward for Larkin to head into the season with this casting a shadow over him and the organization.

But this situation does reinforce that Yzerman doesn’t buckle easily.

How does this apply to Larkin?

Elements of both trade sagas could be relevant to Yzerman’s present situation with Larkin.

St. Louis’ standing with the Lightning is more comparable to Larkin’s in Detroit. Yzerman trading St. Louis to his preferred destination is particularly notable because of Larkin’s limited list. But St. Louis was also 38, and although Yzerman got a strong return for him in the circumstances, Larkin’s age, contract and role as No. 1 center will mean the bar for a suitable return will be higher this time around.

Can the Wild meet that price? They have two former first-round picks in Danila Yurov and Charlie Stramel, who could be interesting to the Red Wings, but Detroit may need a bigger headliner than that to get a deal done.

Meanwhile, the Drouin saga illustrates Yzerman’s willingness to wait for the right deal. It is indeed different dealing with a young player who can be sent to the minors. But in both trades, Yzerman made sure to get a credible return — even when, in Drouin’s case, it meant waiting over a year.

Going into the season with this hanging over the Red Wings would be far from ideal for anyone, but it might still be better than taking a sub-standard return for one of the franchise’s most important players.

Of course, the hope for all involved will be that it doesn’t come to that. The resolution of St. Louis’ request offers some hope that Yzerman can find a suitable solution to an otherwise ugly situation. But both the scrutiny and the degree of difficulty may be even higher this time around.

In the same way the Drouin and St. Louis trades became crucial moments in Yzerman’s Tampa Bay legacy, how he handles Larkin will go a long way to defining his tenure in Detroit.

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