The Ottawa Senators have been here before, just not quite in the same fashion.

Since entering the league in 1992, the team has picked in the top five of the NHL Entry Draft a total of seven times. The players chosen have ranged from total home runs to complete and utter misfires, but the Senators have never had an opportunity quite like this one. In franchise history, they’ve never had two picks in the top five.

Even with this many picks, and this high in the draft, a lot goes into finding the best players, perhaps more so. History is, of course, the best teacher for matters like this. So let’s take a deep dive into the Senators’ seven top-five selections over the past 28 years, and see what we can glean from the players chosen, and how they turned out.

1992: 2nd Overall - Alexei Yashin (Centre)

The first ever draft pick in franchise history, there’s no denying that Alexei Yashin was the Ottawa Senators’ first homegrown superstar.

His offensive acumen was incredible, roaring out of the gate with 79 points in his first 83-game season (1993-1994). From there, Yashin powered the Senators offensively every season, totalling 491 points in 504 games over seven campaigns, serving as captain for the 1998-1999 season.

Of course, there is the matter of why he didn’t remain captain.

Yashin’s tenure with the Senators was tumultuous at best. He faced intense criticism for failing to produce in the playoffs, but most vitriol was directed at his antics off the ice. Various contract hold-outs, and trade demands resulted in captaincy being transferred to Daniel Alfredsson. This led the team, the fans, and the league in general to sour on Yashin, culminating in him being traded to the New York Islanders in 2001, for a package including the second overall pick that year (we’ll get to that).

Off-ice turmoil aside, Yashin remains one of the most productive Senators of all time, and is a prime example of the high-end talent the team wishes to find in this year’s draft.

1993: 1st Overall - Alexandre Daigle (Centre)

Touted as a can’t-miss prospect - so much so that the Senators were accused of tanking in order to get him - Alexandre Daigle entered the NHL with a cargo train full of hype. In fact, one of the reasons for the team’s conflicts with Yashin was them appearing to hold the French-Canadian in a higher regard. This included, but was not limited to paying Daigle more, and advocating for him to win the Calder trophy ahead of Yashin.

You all know the story, I won’t belabour the point: Daigle did not come close to living up to his hype. Never breaking 51 points in a season - a mark he only hit twice in roughly four and a half seasons with the Sens - Daigle crashed and burned upon entry into the NHL. Despite a lucrative contract, Yashin outplayed Daigle by every metric, with the Canadian being criticized for his lacklustre effort, and uninterested attitude. His legacy in Ottawa was marred by coaches being fired for demoting him to the fourth line, and being kicked off a team flight for a bomb joke (seriously, look it up).

Despite the long-held frustration in Ottawa, perceptions of Daigle have softened over the past few years. In 2017, he gave an interview to TVASports, opening up about his struggles with depression that derailed his career.

The Senators can hardly be blamed for passing on Daigle, but it’s a bitter pill to swallow when the likes of Chris Pronger and Paul Kariya were taken after him, and the Quebec Nordiques were rumoured to offer up names likes Owen Nolan, Peter Forsberg, and Ron Hextall. To say nothing of any draft picks.

1994: 3rd Overall - Radek Bonk (Centre)

Though it took him a few years to find his footing, Radek Bonk eventually emerged as the Senators’ top centre after Yashin’s departure.

In his first five seasons with the team, Bonk managed a high of 35 points, much to the dismay of a fanbase still trying to rinse the bitter taste of Daigle out of its mouth. During the 1999-2000 season, however, Bonk exploded for 60 points in 80 games, and over the five seasons from ‘99 to ‘04, notched 287 points in 372 games. He also established himself as a playoff performer, and reliable two-way forward in the rigid Jacques Martin system.

While Bonk never matched the level of offence provided by Yashin, he’s a great example of a top Sens prospect done right. The team didn’t rush him; slowly ramping up his icetime, and allowing him to grow within the system before being thrust into a top six role. His average icetime increased from 13:44mins in 1998-1999, to 18:14mins in 1999-2000, and their patience paid off in the form of a player who was vital to the team’s first taste of success.

1995: 1st Overall - Bryan Berard (Defenceman)

If you’re sensing a pattern here, it’s because we’re about to delve into another messy divorce between the Ottawa Senators and a top draft pick.

Bryan Berard roared into the 1995 NHL Entry Draft, scoring 75 points in 58 OHL games with the Detroit Jr. Red Wings. The Woonsocket, Rhode Island native was an easy choice for a Senators team beginning to find some offence, but still lacking on the back end.

Berard would never play a game for the Ottawa Senators.

The first American to be selected first overall by a Canadian franchise, Berard was taken aback upon finding out that after what he characterized as “a pretty good camp”, the Senators were sending him back to junior for one more year. He asked for a trade, and was accommodated by being sent to the Islanders, in a package that sent Wade Redden and Damian Rhodes back to Ottawa.

It’s a “he said/she said” situation, of course, but Berard was recently quoted as saying “it’s like they just did not want to pay me that year”, and pointed to the generally sub-optimal state of the franchise at the time. We may never know the true details of what happened here, but it seems like a relationship that was always doomed to fail.

1996: 1st Overall - Chris Phillips (Defenceman)

Any way you slice it, Chris Phillips was the first time that the Ottawa Senators knocked a Top-5 draft pick out of the park. Though Yashin and Bonk may have provided more in the way of points and offence, the Senators got something out of Phillips that they desperately needed: stability.

The defensive stalwart from Calgary would go on to play nearly as many games in an Ottawa uniform as Yashin and Bonk combined - 14 shy to be exact - and became a key figure on a burgeoning Senators team.

After another season in junior (*coughs*), Phillips joined the Senators, and provided the defensive impact they had hoped for. He helped the team eliminate the New Jersey Devils in the first round of the 1998 playoffs for the their first postseason series victory, and was one of the foundational players in their prime days of contention. From the 2003 Eastern Conference Final run and his famous overtime goal, to the 2007 Stanley Cup Final, Phillips was a lockdown defenceman in Ottawa’s greatest days of success, and was a key contributor to them.

With this pick, the Senators not only found one of the league’s more underrated stay-at-home defenders, but one of their all-time great leaders, as well. He served as an alternate captain for nine seasons, and firmly cemented his place as a pillar in the community.

People may point to his lower point totals, but Phillips is the exact kind of player and person that the Senators should be targeting. Upper-end ability, and captain material in the room.

2001: 2nd Overall - Jason Spezza

As part of the aforementioned Yashin trade with the Isles, that somehow also yielded Zdeno Chara, the Senators also owned the second overall pick in the 2001 NHL Entry Draft. It ended up being a young Toronto native named Jason Spezza.

Mike Milbury is the greatest GM in Ottawa Senators history.

Though he was wet behind the ears upon being drafted, and faced a learning curve in a Jacques Martin system that favoured defence, it wasn’t long before Spezza emerged as one of the NHL’s elite playmaking centres. He impressed during 33 games in the 2002-2003 regular season, but truly arrived in that year’s Eastern Conference Final.

From there, and especially after the lockout of 2005, Spezza became a bonafide playdriving centre for Ottawa. Anchoring the Pizza Line with Dany Heatley on his left and Daniel Alfredsson on his right, much of the team’s offence went through Spezza, and as he went, so did the Senators. Tallying more assists than goals every season, he was as high-end a playmaker as one could find.

After 686 games in Ottawa, and a brief stint as captain, Spezza was traded to the Dallas Stars in 2014. Chronically under-appreciated during his time in the capital, he remains second in franchise history in goals, assists, points, powerplay goals, and game-winning goals.

Frankly, if either of Ottawa’s top five selections in 2020 come anywhere close to Spezza’s levels of production, it would be a massive win. The team is in dire need of game-breaking talent, especially up the middle. With the likes of Quinton Byfield, Tim Stuetzle, and Marco Rossi in play, Pierre Dorion and Co. are surely hoping for something along the lines of a Spezza 2.0.

2018: 4th Overall - Brady Tkachuk

After seventeen years spent outside of the top five, the Senators unceremoniously flopped back into it with an almost impressively bad 2017-2018 season. Having the choice to send either their 2018 first, or 2019 first to the Colorado Avalanche, Dorion elected to keep that year’s selection, which ended up being the fourth overall choice.

The Senators selected Brady Tkachuk, and the pick was met with widespread acclaim. Wait...why are you Googling that? Is my word not good enough for you?

While he’s only played two seasons, young Brady has become fan favourite. His attitude, and tenacious play style has endeared him to a fanbase dying for some faint sliver of hope to latch on to. Impressive point totals aside, Tkachuk has produced offence at a level only seen in the league’s top class. In fact, I dissected his first two years, and compared them to those of Mark Stone, in this piece here.

Though it’s early, Tkachuk is a prototypical home run draft pick in every sense. He’s effective in all aspects of the game, and provides an amount of leadership and character rarely seen in players ten years his senior.

Tkachuk is everything the Sens should be looking for in this draft, and more.

“Those who don’t learn from history are doomed to repeat it”, so what can we learn from 22 years, and seven top five selections?

Well, as far as talent goes, we know the Senators are capable of finding the right guys. Every one of the aforementioned selections was at least capable of producing at a high-level, though their roles may have differed. That said, it seems apparent that the Senators are looking for more offence than defence in this year’s top five.

However, talent isn’t everything. For all the flack Pierre Dorion gets for trying to bring in “character guys”, there is serious merit to avoiding bad attitudes, in both the short and long term. For every Phillips, Spezza, or Tkachuk, there can also be a Berard, a Daigle, or a Yashin.

There is not a shred of evidence to suggest that any future Sens would present similar issues, but the team needs to lock down players that they know will be pillars on and off the ice for years to come.

To refine this a little further, there’s one pick that leaps out to me as the type of all-around player and person that the Senators need: it’s Jason Spezza.

Ottawa needs a point-a-game player, especially a centre. They need a guy up the middle who can feed the likes of Tkachuk, Drake Batherson, and Anthony Duclair, and power a high-octane offence by extension.

In the locker room, Spezza was a guy that his teammates, and the media always raved about. Pleasant to be around, led by example, and has a hockey mind so strong that folks around the game regard him as a future GM.

Regardless of who they take, the Senators will be getting a wealth of talent from their picks. Tops on their list of priorities, however, needs to be a play-driving centre, that can also be a source of leadership when the going gets tough.

If they can avoid their previous mistakes, and recapture their previous magic, then the future is going to very bright in Ottawa.