A Trip Down Memory Lane: The 10 biggest trades in Sens History

Well, we’re mid December and there’s still no NHL hockey, and very little Sens news to speak of. So what do you do when there’s no new developments to cover? You reminisce, of course.

Like any other NHL franchise, the Senators have had their share of home runs as well as head scratchers over the years on the trade front. Going back through the Senators trade history was both nostalgic and eye opening. Granted the ability of hindsight, you suddenly feel like the smartest person in the room. You wonder aloud how anyone thought it was a good idea to trade Pavol Demitra (768 career pts) for Christer Olsson (16 career pts) straight up in 1996. Whoops. Or why in 1923 the team got fleeced by the Hamilton Tigers by paying THEM cash for Leth Graham who wouldn’t score a single point for the Sens over the next 3 seasons! I’ll admit I may have gone down the trade history rabbit hole a bit too far.

In any case, here are the 10 most franchise-altering trades the Sens have made in modern team history. Some for the better, some for the worse, and all up for debate.

Honourable mentions:

These guys just missed out on the cut because the deals didn’t quite move the needle enough, or weren’t sufficiently infuriating to make the grade . Better luck next time.

Alex Daigle → Pat Falloon, Vaclav Prospal, 1998 2nd rd pick (which became Chris Bala)

JG Pageau → Islanders 2020 1st & 2nd rd. picks (conditional 3rd did not materialize)

Mike Fisher → 2011 1st rd & 2012 conditional 3rd

Brian Elliott → Craig Anderson

Mika Zibanejad & 2018 2nd rd pick → Derick Brassard & 2018 7th rd pick

Nick Foligno → Marc Methot

Jakob Silfverberg, Stefan Noesen, 2014 1st rd (Nick Ritchie) → Bobby Ryan

Jason Spezza & Ludwig Karlsson → Alex Chiasson, Alex Guptill, Nick Paul, 2015 2nd rd

#10) Sens trade their 2010 1st rd pick (16th overall) to St. Louis for David Rundblad

At first glance, this doesn’t seem so bad. What team doesn’t get enamoured with a prospect who doesn’t pan out from time to time? The problem is that St. Louis would go on to use that pick to take Vladimir Tarasenko, who in his last 5 full seasons has posted goal totals of 37, 40, 39, 33, and 33 respectively. The Sens, on the other hand, made the trade for Rundblad on June 25th 2010. By Dec 17th 2011, the organization had already soured on him and traded him as part of the Turris deal. Grand total production out of Rundblad in Ottawa? 24 games, 4pts and a -11 rating. Management would probably like a do over on this one.

#9) Sens trade Ben Bishop to the Lightning for Cory Conacher & a 2013 4th rd pick

I promise this list will not be made up entirely of Senators misfires over the years. Good trades are coming, people! But to get to the good, we have to sift through the wreckage of a few miscalculations. One such blunder would be trading a 6’7” goalie entering the prime of his career for a 5’8’’ (maybe on skates) undrafted forward. Ben Bishop (who, even in a crowded Ottawa crease, was largely viewed as the player with the most upside in the organization) would go on to set franchise records for Tampa Bay and be nominated for 3 Vezinas. Cory (whom I’m sure is a lovely person in real life) unfortunately would go on to have a 72 game stint with the Sens potting a paltry 6 goals before moving on. The kicker? HE WOUND UP BACK WITH TAMPA. So in the end, the Sens moved a perennial Vezina finalist for a 4th round pick. Makes you wonder how Ottawa would have fared with their existing pieces + a Tarasenko/Bishop injection into the dressing room. Likely a very different decade if that were the case.

#8) Sens trade Martin Havlat & Brian Smolinski to the Blackhawks for Michal Barinka, Josh Hennessy, Tom Preissing, & a 2008 2nd rd pick (Patrick Wiercioch)

The Martin Havlat era was the equivalent of eating Chinese food. It was nice while it lasted, but ultimately it left you wanting more. Which is why his departure was inevitable. The organization gets points here for having the wherewithal to get something before he left via free agency. But how does an organization do a 6 player deal and still somehow end up giving up the only two assets of note in the trade? You would have liked for them to have gotten at least one top six player in return for a talent like Havlat (injury prone as he may have been), and a usable player like Smolinski. Preissing only lasted one season in the Nation’s capital, Hennessy was unable to establish himself at the NHL level (23 games over 5 seasons between Ottawa & Boston), and Michal Barinka (who I had to double check was indeed a real person and not a typo) played 17 games for Binghamton before returning to the Czech Republic never to be heard from again. The Sens were at least able to get 200+ games out of Wiercioch before he moved on, but anytime you flip a franchise cornerstone you’d like to get a bit more in return.

#7) Sens trade Mark Stone to Vegas for Erik Brannstrom, Oscar Lindberg, and a 2020 2nd rd pick

Hated this trade when it happened, and still not sold on it yet either. I’m hopeful that Brannstrom will prove me wrong on this deal and will mature into the elite puck moving defenseman he was projected to be. He’s still a baby by NHL blue liner standards (21 years old) so the jury is still out. But given the glut of defensive players under the age of 23 currently in the Sens system (Sanderson, Bernard-Docker, Guenette, Wikstrand, Chabot) who project to get a shot at NHL playing time in the future, you’d have to think that the Sens would probably prefer a bonafide top line player than another defensive prospect. While the offensive output is certainly missed, it’s all the little things that don’t show up on a stat sheet that Stone does as good or better than anyone else in the league that really hurts. The takeaways, puck pressure, and removing opposing passing lanes on rushes that are key components to Stone’s game have yet to be replaced. Not to mention he was a fan favourite and great in the community. Big shoes to fill Erik, let’s hope you’re up to the task.

#6) Sens trade Bryan Berard, Don Beaupre & Martin Straka as part of a multi-team trade and receive Wade Redden & Damian Rhodes

The optimism Sens fans had when they selected Bryan Berard 1st overall in the 1995 entry draft was short lived. Depending on whose side you take, you’ll either believe that Berard had some maturing to do and felt entitled upon his arrival to an NHL camp (management’s belief) or that the Sens were poorly managed, attempting to tank again for another high draft pick, and had some unscrupulous contract negotiation techniques (Berard’s belief). Whatever the case, Berard became expendable in a hurry when he balked at the team’s attempt to re-assign him to the minors. The result would end up being one Sens fans are likely pleased with, as the team was able to secure Redden and Rhodes in a three team deal with the Leafs and Islanders. Which begs the question, why don’t we do more trades with the Islanders? Between this, the Pageau trade, and another one we’ll get to in a moment, the Sens look like geniuses every time they call Long Island. Someone make Lamiorello’s number a speed dial option on Dorion’s cell immediately.

#5) Sens trade their 2008 draft 18th overall pick & a 2009 3rd rounder for Nashville’s 2008 1st rounder, 15th overall (which would become Erik Karlsson)

Probably not the Erik Karlsson trade you were expecting to see on this list. Don’t worry, that one’s coming. But sometimes you need to celebrate the smaller moves that end up paying off huge down the line. This trade is the perfect example of that. For whatever reason, the Senators seem to have better luck when trading picks for picks on draft day than they do for fully materialized NHL players. Perhaps this is a testament to Dorion & Mann’s amateur scouting ability. However, if you’re to believe that, then what does this say about the organization’s professional scouting ability? But I digress… The most obvious example of draft day success would be in 2008 where the team was able to secure 2x Norris winner and franchise icon Erik Karlsson with the 15th selection in the first round. Not bad for what would amount to be Chet Pickard (Nashville’s selection at 18th overall) and Taylor Beck (Nashville’s 3rd rounder the following year). I don’t need to bust out the NHL trade simulator to know that Karlsson for Pickard & Beck is a trade you make 100 times out of 100.

#4) Sens trade Shane Bowers, Andrew Hammond, 2018 Conditional 1st (Bowen Byram), 2019 3rd (Matt Stienburg) to Colorado for Matt Duchene

Remember this trade a few years from now, because it has a chance to climb up the list for all the wrong reasons for Sens fans. Hammond was a nice story, and he’s earned his place in Sens' folklore but he was never a long term solution in the Ottawa crease. Matt Stienburg is currently at Cornell (home of alumnus Andrew Bernard), and is a few years away from turning pro. But where it will likely get ugly fast for the Sens is Bowers and Byram. Both have great chances at breaking camp with a loaded Colorado team this year once the season gets up and running, and are poised to play big roles for the Avalanche immediately. We learned with the emergence of Cale Makar that Colorado isn’t afraid to give big minutes to rookies early on. Byram could have a similar trajectory (perhaps not as high of an offensive ceiling) right from the get go. Expect for him to star for Team Canada at the World Juniors this year, and then be in the conversation for the Calder trophy in the show. Bowers projects to be an NHL caliber forward who, if he gets slotted in on one of the Avalanche’s top two lines, could force his way into the Calder conversation as well. If Mackinnon and Co. wind up becoming the 2nd coming of Sakic’s late 90’s teams, expect to hear the names Byram and Bowers a lot over the next 5+ years of your life. All that for 1 and a half seasons of Matt Duchene (who I actually really liked while he was in Ottawa). Steep price to pay for a player on a team that was apparently on the brink of a tear down anyways. File this one away under “to be reviewed” a few seasons from today.

#3) Sens trade Greg Devries & Marian Hossa to Atlanta for Dany Heatley

Hey, remember when Atlanta had a team for a 2nd time? Seems so long ago. This is one of the rare trades involving star players in pro sports where both teams can viably say they would probably make the same deal today knowing how it all played out. It’s tough to see one of the most gifted offensive players in Senators history and a future hall of farmer leave no matter what the circumstances. But the Alfie-Spezza-Heatley “Pizza Line” was one of the most electrifying eras in Ottawa sports history. The clip at which the Sens scored goals during those years was unparalleled for the franchise. So much so, that Pizza Pizza (whom you could exchange tickets for pizza slices the day after Sens home games) had to change the rules around their promotion several times over the course of Heatley’s time in Ottawa. The three amigos were scoring goals faster than their pizza ovens could crank out pies. I still remember being at our family cottage when I saw news of the trade break across the ticker at the bottom of our screen. When I told my Dad (who was in the other room) the news he screamed “THEY DID WHAT?!?”, then went quiet. About a minute later after processing it, he came into the room and exclaimed “ya know what I’m OK with that trade” which is probably the perfect way to describe this deal. Shocking at the time, but fast forward a decade and both teams would probably still do it again.

#2) Sens trade Karlsson & Francis Perron to San Jose for Josh Norris, Chris Tierney, Rudolfs Balcers, Dylan Demelo, 2019 2nd rd, 2020 1st (Stuetzle), 2021 2nd rd (conditions for 1st not met), no additional 1st rd pick by 2022 (the “Hoffman” clause about Karlsson not being on an Eastern Conference roster in the 2018-19 season)

I will be the first to admit that I have come full circle on this trade. When it first happened I thought “San Jose did it again, they fleeced us”. My view was that Tierney/Balcers/Demelo

would likely be short term players who would ultimately never get re-signed by the team. I also thought Norris was a decent prospect, but was part of the deal mostly because he was besties with Tkachuk, not because he could potentially be a top 6 NHL forward. And finally that Karlsson would continue producing at an all world level, and San Jose’s picks would be in the 25-31 range for the next couple seasons.

In the famous words of Michael Scott “Well, well, well, how the turn tables…” (that’s two Office references thus far for those keeping score at home). If you predicted in the moment that Karlsson would immediately regress, that the Sharks would crumble and their pick would wind up being a top 3 selection, that Norris would be named to the AHL’s all rookie team AND 1st team all star, and that the Sens would actually make a rare re-signing for Tierney at a super cap friendly 2yr / $3.5M deal then go buy a lottery ticket now. The stars could not have lined up any better for the team. If Stuetzle & Norris wind up being only 75% as good as they’re looking right now, this will likely go down as the #1 deal in franchise history. But for the moment I can’t in good conscience make it any higher as they’re still just prospects and who knows what the future holds.

***Side note: My favourite part of this entire deal is that Dorion was genuinely afraid that San Jose was going to pull another fast one on him. So much so that they actually included a “Hoffman Clause” in the deal whereby if the Sharks traded Karlsson to an Eastern Conference team they had to give an additional first to the Sens. Classic.

#1) Sens trade Yashin to the Islanders for Bill Muckalt, Zdeno Chara, and a 2001 1st rd pick (Jason Spezza)

Remember how I alluded to the Islanders making another glorious appearance on this list? Well it just so happens that they’re the number one trade the Sens have ever made. Not only did they rid themselves of a distressed asset (Yashin was fresh off being stripped of the captaincy after sitting out the entire 1999-2000 season amidst his 3rd contract dispute with the Senators in 5 seasons), but they acquired two pillars of the franchise that propelled them to heights they’d never been before. I cannot for the life of me remember a single Bill Muckalt highlight but according to his hockeydb profile he played 70 games for Ottawa and had 0 goals & 8 assists in 2001-02. “Oh, he must be a defenseman”. That’s a good initial thought, and where my mind went first as well. Nope, he was a right winger. “Oh he must have been an enforcer then”. Nope, only had 46 PIMs. What the heck happened that year? The next year he suffered an injury with Minnesota and unfortunately had his career cut short, but he’s now the Associate HC at the University of Michigan so he’s doing alright for himself. Chara and Spezza would become fan favourites and perennial all-stars. Yashin on the other hand, signed an absurd contract with New York and became essentially untradeable. 5 years later he was out of the NHL entirely. I’d say the Sens did alright for themselves here