Tuesday, July 9, 2019

Playing “What if?” with four of the cap era’s biggest free agency decisions

We’re over a week into the free agency period, which means most of the big decisions have already been made. And we’ve seen plenty. The Canadiens chose to try an offer sheet on Sebastian Aho, and the Hurricanes chose to match. Artemi Panarin chose the Rangers over the Islanders and Blue Jackets. The Panthers chose to give $70 million to a goaltender. And the Predators chose to finally do whatever it took to land Matt Duchene, even if it meant giving up P.K. Subban.

Will some of those decisions turn out to be mistakes? Probably. That’s the beauty of this time of year. The GMs, owners, players and agents make the best choices they can, and the rest of us get to watch and see how it all turns out.

That’s always been the fun part for me, because I love a good round of “what if?” I mean, I really love it. I’m the guy who once wrote an entire alternate history of the NHL based on the Tom Kurvers trade never happening. I may have a problem. But I’m betting at least a few of you are right there with me.

So today, let’s look back on four key free agency-related scenarios from the salary cap era, and how history may have changed if they played out differently. As we’ll see, the decisions that get made at this time of year can have profound and sometimes unexpected impacts – not just on the teams and players involved, but on what does (and doesn’t) happen around the league as a result.

2006: What if the Senators choose Zdeno Chara over Wade Redden?

The situation: One year into the cap era, the Senators were Cup contenders who’d just finished the 2005-06 season with the best record in the East. But they were faced with a tricky offseason dilemma. Each of their two best defensemen, Wade Redden and Zdeno Chara, were on the brink of unrestricted free agency. And the team decided that they only had the budget and cap space to re-sign one of them.

So who would it be? Both players were coming off excellent seasons; Chara had finished fourth in Norris voting, while Redden was fifth. Chara was a rare combination of size and skill who’d taken a while to find his game in the NHL but had developed into one of the best defensemen in the league since being traded to Ottawa, having been named a first-team all-star in 2004. Redden hadn’t quite hit those heights but owned a longer track record, having been a consistent presence on the Ottawa blueline for a decade. Along with Daniel Alfredsson, he was the face of the franchise.

You can pick one. Who do you go with?

What happened: The decision went down to the wire, but ultimately the Senators chose Redden, re-signing him on the eve of free agency to a two-year extension that carried a $6.5 million cap hit. Chara became a UFA, and quickly signed a five-year deal with the Bruins with a $7.5 million cap hit.

Needless to say, it all worked out brilliantly for the Bruins. Chara has had 13 years and counting in Boston; he’s been a postseason all-star five times, won a Norris and been a finalist four other times, and led the team to a Stanley Cup in 2011. He’s almost certainly the greatest free agent signing of the cap era, and maybe even of all-time.

Redden finished out his two-year extension in Ottawa, playing reasonably well if not quite at an all-star level, before needing a new deal again in 2008. This time, the Senators couldn’t keep him, and even tried to get him to waive his no-trade clause on multiple occasions. He refused, denting his reputation with some Senators fans in the process, and eventually signed a six-year contract with the Rangers on the first day of free agency. That deal ended up being a bust, and Redden spent much of it in the AHL.

At the time, it had seemed like a tough call. In hindsight, it couldn’t have been more lopsided. And the Senators chose wrong.

But what if… : First things first. A lot of the “Redden vs. Chara” narrative has always felt a little too convenient. We don’t know a lot of what happened behind the scenes, including whether Chara ever really wanted to stay in Ottawa in the first place. It’s possible that the Senators just re-signed the player who wanted to stay to the best deal they could, and the rest of it is just a dramatic storyline slapped on top of some fairly standard cap management.

But that’s no fun. So let’s pretend that the Senators really were faced with an either/or choice. What if they’d chosen Chara, on the same sort of five-year deal he got from Boston?

Well, the first repercussion is that a big chunk of their fan base is furious. That’s the part of the story that gets skipped over these days, but as a hockey fan living in Ottawa at the time, I can tell you that it’s hard to overstate just how popular Redden was. He had his occasional detractors, like any player. But for most of his time as a Senator he was the golden boy, and the fans didn’t want to see him go.

Are the Senators better with Chara instead, even at a higher salary? In hindsight, absolutely, although it’s worth remembering that Redden helped them get to the Stanley Cup final in 2007. Do they win that final with Chara in the lineup? They might. And they almost definitely manage more than the two playoff game wins they had over the following four years. Could they have kept Chara on another deal beyond that? That gets dicey, but even if he’d bolted after five years, they’d have still come out ahead compared to two years of Redden.

Meanwhile, the Bruins lose out on their captain, and probably their 2011 Cup too. More bad news: they would have had an extra $7.5 million to spend in that 2006 offseason. Do they throw it at another blueliner, like Ed Jovanovski or Pavel Kubina? Or maybe one of the big forwards like Alex Tanguay or Martin Havlat? None of those options look great in hindsight. Take Chara off the market in 2006, and the next decade-plus of Bruins history starts to look very different.

On that note, here’s one more what-if to consider: What if Chara had hit the market, but chosen not to sign in Boston? According to reports, the other main bidder was the Los Angeles Kings. Would Chara have been as dominant in Los Angeles as he was in Boston? Probably. But that might not have been a good thing. If Chara improve the rebuilding Kings by just a few wins by Year 2, that moves them out of the second-overall pick in the 2008 draft, and probably makes Drew Doughty an Atlanta Thrasher. Do the Kings win two Cups with Chara instead of Doughty? And if you want to really get crazy, do the Thrashers improve enough after adding Doughty with the second-overall pick that they’re not in Winnipeg today? Bruins fans are happy that we never got to find out.

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