Before the clock struck three: Part 1

Screen times spike annually on trade deadline day for fans and general managers alike, as fans refresh their feeds desperately hoping their team has swung a deal that could change the course of their franchise, while general managers fire trade proposals back and forth as they race against the clock.

For years, the day has stood as one of the most exciting days on the hockey calendar. Whether your team is looking for a depth add to push their playoff hopes over the top, taking a big swing that could help bring home a Stanley Cup, or is looking to cut bait on some unrestricted free agents and pick up some futures in return, the deadline offers hope for everyone.

The Senators have made 40 deals on deadline day in franchise history and have stood pat just five times. Here’s a look back at the most notable of those days, from the 2001 deadline up until the 2013 deadline. Part 2, revisiting deadlines from 2014 to 2025, will be released Thursday.

March 13, 2001: Senators add Curtis Leschyshyn and Mike Sillinger

The team’s deadline acquisitions of Curtis Leschyshyn and Mike Sillinger combined for a goal in their first game as Senators. Leschyshyn, acquired from Minnesota for a third-round pick, was a depth defenceman at that point in his career, brought along to help bolster the blueline for the playoffs.

Sillinger, meanwhile, infamously holds the record of being traded the most times in NHL history. The return in this one may have been the most unique. The Senators had sent Vinny Prospal to Florida just two months prior for a conditional 2001 fourth round pick or 2002 third round pick. The pick would be returned back to Florida in exchange for the two-way centre.

“Florida offered me a contract right at the deadline,” Sillinger recounted to The Athletic’s Daniel Nugent-Bowman in 2019. “They said, ‘If you don’t sign this contract, we’re gonna trade ya.’ We were in contract negotiations for about a month or three weeks before the deadline. It was hardball contract (talks). I get pulled off the ice in the pregame skate. I’m sitting in the room with the GM and the coach. They’re explaining, ‘If you don’t sign this contract, this is it.’

Sillinger, the ultimate Puckdoku answer, would record three of his 240 career NHL goals with Ottawa and seven of his 548 career points. The Senators were ultimately swept by the Leafs in the first round of the playoffs.

Leschyshyn signed a three-year, $6 million contract with Ottawa in the offseason and appeared in an even 200 regular-season games and 36 playoff games in total with the club.

March 11, 2003: Senators acquire Bryan Smolinski

The Senators drafted Tim Gleason 23rd overall in the 2001 entry draft, and the gritty defenceman looked like a lock for at least a middle or bottom pairing in the NHL as he continued his junior career with the Windsor Spitfires. But the team and the prospect couldn’t agree on terms for a contract, leading Gleason to be used as trade bait at the 2003 deadline.

Gleason’s rights were sent to Los Angeles in exchange for Bryan Smolinski. A versatile centre who could play up-and-down the lineup, Smolinski was widely expected to be a rental for the Sens — he even said as much at the time. “I would welcome anything when it comes to July 1,” Smolinski said after the trade. “If it’s the Kings, that would be great. We still live there. It was tough to leave.”

But after a good end to the regular season — three goals and five assists in 10 games — Smolinski was won over by the Senators and their depth. He contributed two goals and seven points in 18 playoff games. 

"Looking on the outside in, it's sickening how young they are and how everyone wants to score," Smolinski said in May, after the Senators won Game 1 of the Eastern Conference Finals over New Jersey. "You can throw the ball up in the air and pick four lines. It's sick the depth that we have."

Smolinski would end up re-signing a four-year contract extension with Ottawa after the playoffs. He recorded seasons of 46 and 48 points sandwiched around the 2005–06 lockout before being shipped to Chicago alongside Martin Havlat.

March 9, 2004: Senators acquire Greg de Vries, ship out Shane Hnidy

With New York Rangers general manager Glen Sather holding an All-Canadian fire sale, the Senators picked up defensive defenceman Greg de Vries on deadline day in 2004 in exchange for depth defender Karel Rachunek and 1999 seventh-round draft pick Alexandre Giroux. 

Sather had signed de Vries to a four-year, $13 million contract just the summer before the trade, leading the media to question Senators general manager John Muckler whether or not Sather had picked up any of the money remaining on the deal. "I have no comment on that, I'm sorry," Muckler said at the time. "But it's a good question." 

de Vries would play 13 regular season games and seven playoff games before being involved in a much more important deal in Senators history. After the 2004–05 lockout ended, de Vries was traded with Marian Hossa to Atlanta in exchange for Dany Heatley.

Earlier in the day, the Sens also traded Shane Hnidy to Nashville in exchange for a third-round pick that became Peter Regin. Regin played parts of five seasons in Ottawa, and scored three goals in the Sens’ first-round playoff loss to Pittsburgh in 2010.

February 27, 2007: Senators acquire Oleg Saprykin in exchange for second-rounder

With Heatley, Spezza, and Alfredsson having a season for the ages, and Mike Fisher, Peter Schaefer, Antoine Vermette, Chris Kelly, Chris Neil, and the midseason acquisition of Mike Comrie providing secondary scoring, there was no need for Muckler to make a swing for a scorer at the 2007 deadline. Instead, he added bottom-sixer Oleg Saprykin. 

"He could play pretty well anywhere," Muckler said at the time. "We're going to run into injuries throughout the playoffs, we have a depth defenceman, we now have a good support staff for the regular players. He makes us a better hockey club because there's more depth on the hockey team. That's something we haven't had in the past."

"It's great to go to Ottawa," Saprykin said after being traded. "It's good that everybody there expects to play in the finals of the Stanley Cup.”

Indeed, the Senators were headed for the franchise’s first-ever Stanley Cup Finals. Saprykin played 15 out of the team’s 20 playoff games, scoring the game-winner in the Game 1 of the Eastern Conference Finals, a 5-2 win over Buffalo.

March 4, 2009: Senators swap Vermette for Leclaire and a second-rounder

Drafted 55th overall by the Senators in 2000, Antoine Vermette had cemented himself as one of the league’s best faceoff men and two-way centres by the age of 27. 

With Vermette under contract through the following year — at just $2.76 million per season — and the Senators well out of the playoff race on deadline day in 2009, he was sent to Columbus for starting netminder Pascal Leclaire and a second-round draft pick.

As the Senators were stuck at the bottom of the Northeast Division standings, Leclaire took the rest of the season to recover from an ankle surgery and returned healthy to start the 2009–10 season. But due to a litany of other injuries, mainly a bad hip, he was forced to retire at the age of 30, having played just 48 games over two seasons in Ottawa.

Thankfully, the Senators also acquired a second-round pick in the deal that was used on another goalie, Robin Lehner. The ‘Panda’ started 76 games in Ottawa but would see better career success after a trade to Buffalo, in which the Senators obtained the right to draft Colin White.

March 2, 2010: Senators acquire Andy Sutton

While it did come in a day before the deadline, we’ll make a small exception. The Senators traded a second-rounder for the 6-foot-6 behemoth Andy Sutton, helping to add some experience and physicality for a potential playoff run. 

"Islanders GM Garth Snow\] knew what he could get elsewhere and he was certainly fielding questions from other general managers," [said Murray at the time. "At the end of the day he came back and we talked and I guess I owe him something or vice versa, but we were able to make the deal."

Sutton played 18 regular season and six playoff games in Ottawa, and ended up laying a devastating and well-publicized hit in the Sens' first round series against Pittsburgh, knocking Jordan Leopold unconscious. The Sens would end up losing in six games to the Pens.

Three weeks before the Sutton trade, the Sens picked up veteran forward Matt Cullen in exchange for another second-round pick, making it one of their more active shopping sprees before the deadline in team history.

Cullen scored four goals and four assists down the stretch run in the regular season and led the team in playoff scoring with three goals and five assists.

April 3, 2013: Senators flip Bishop for Conacher

Only a year after shrewdly swapping a second-round pick for the massive Ben Bishop, the Senators decided to sell from a position of strength with Bishop stuck behind Craig Anderson and Robin Lehner on the depth chart.

It’s anyone’s guess how Bishop’s career would have turned out in Ottawa — Anderson remained their starting netminder for seven more seasons. But it certainly turned out well in Tampa Bay, where he played to a sparkling 2.28 goals-against average and .921 save percentage over parts of five seasons, and in Dallas (2.33 and .923 over three seasons). 

Meanwhile, for the undrafted and undersized Conacher, Ottawa was not what the doctor ordered. He never again matched his nine goals or 24 points he had recorded with the Lightning to that point in the season and was waived under a year later. 

There was a silver lining to the trade, though. Conacher would come up big in the playoffs that year for the Sens, scoring the game-tying goal against Montreal in Game 4 of that season’s first round playoff series with just 23 seconds left to play. He’d also add two more goals in Game 5, though he was also healthy scratched once in that first round and once in their second-round loss to Pittsburgh.

Stay tuned for Part 2 on Thursday!

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