The Absolute Worst Toronto Maple Leafs Trades No One's Heard About

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Few teams have historically been run as poorly as the Toronto Maple Leafs.

The Toronto Maple Leafs have seen many players come and go through the years.

It always stings when someone they had within the organization develops well beyond expectations, only it’s with another franchise.

This has been the case too many times in the organization’s very long history. However, these are usually well known moves. For example, when the Leafs bet on Andrew Raycroft and Justin Pogge to be the future starters in goal, they gave up a young prospect named Tukka Rask who ended up carrying the Boston Bruins for 15 years.

Or when Boston used the draft picks they received for Phil Kessel to draft Tyler Seguin and Dougie Hamilton. Seguin was as good as Kessel, but Dougie Hamilton went on to become one of, if not the best defenseman of his generation.

Lopsided trades like that one live in infamy.

Those well publicized and often discussed transactions aren’t the focus here.

There have been moves made that haven’t received the same level of press. There are the Leafs disaster transactions that have gone under the radar.

Jun 13, 2023; Las Vegas, Nevada, USA; Florida Panthers forward Carter Verhaeghe (23) . Mandatory Credit: Lucas Peltier-USA TODAY Sports /

Toronto Maple Leafs Under the Radar Disasters: Carter Verhaeghe

A 6’2 Toronto Born winger drafted and developed by the Toronto Maple Leafs, who went on to score 40 goals – but not for his hometown team.

The Leafs haven’t developed one of their own low picks into a star since Tomas Kaberle in the late 90s, which goes a long way to explain their lack of success over the last 25 years.

Hockey fans are enjoying Carter Verhaeghe’s heroics this postseason, having helped take his Florida Panthers all the way to the Stanley Cup Finals.

This season, his numbers were incredible. The center played 81 games where he scored 42 goals and added 31 assists for 73 points.

Verhaeghe is the sort of player that the Toronto Maple Leafs would love to have playing for their franchise.

Though he never did step onto the ice in blue and white, he was once with the Leafs. Toronto drafted Verhaeghe in 2013. He was selected in the third round, 82nd overall.

Verhaeghe didn’t last long with the Toronto Maple Leafs.

General Manager Lou Lamoriello included him as part of the package used to trade for Michael Grabner.

The New York Islanders got Verhaeghe along with goaltender Christopher Gibson (played 16 total NHL games), defensemen Tom Nilsson (played 0 NHL games) and Matthew Finn (played 0 NHL games), and forward Taylor Beck (played 92 total NHL games) in a bizarre five for one trade.

Grabner ended up playing 80 games that season, his only with the Leafs. He registered nine goals and nine assists.

Tyler Biggs

Former Toronto Maple Leafs general manager Brian Burke had a type.

He likes his hockey players the same way he likes his coffee, with no sugar but plenty of truculence. It’s likely why he and the Leafs decided to move up in the 2011 NHL Entry Draft.

In order for the Leafs to get their preferred player with the 22nd overall selection, they had to trade the Anaheim Ducks a pair of picks.

The Buds got the 22nd pick in exchange for the 30th and 39th picks. Burke was likely ecstatic when his team used their first round selection to acquire Tyler Biggs.

The 6’3″, 215 lbs right-winger may have been perfect for Burke, but not the NHL. Unfortunately, Biggs never took a shift in the league. While he did play in the AHL, it’s the furthest he managed to get in his hockey career before hanging up his skates for good.

Meanwhile, the picks the Toronto Maple Leafs sent the Ducks in exchange for Biggs had far more success. With the 30th pick, Anaheim took Rickard Rakell.

He’s had a spectacular career, which included back-to-back 33 and 34-goal campaigns for the Ducks. Rakell currently plays for the Pittsburgh Penguins. This season, he played a full compliment of 82 games where he recorded 28 goals and 32 assists. Rakell’s now skated in 651 career NHL games where he’s scored 186 goals and tallied 226 assists for a total of 412 points.

If that was all the Leafs gave up for Biggs, it would be bad enough, but it’s not.

With the 39th selection, Toronto watched the Ducks take goaltender John Gibson. He remains with Anaheim to this day having played over 400 NHL games. He owns the second-most wins in the organization’s history with 180 of them. (Jean-Sebastien Giguere is the franchise leader with 206 wins.)

Travis Dermott #23 of the Toronto Maple Leafs checks Travis Konecny #11 of the Philadelphia Flyers during the second period at Wells Fargo Center on January 18, 2018 in Philadelphia, Pennsylvania. (Photo by Patrick Smith/Getty Images) /

Travis Konecny (and Sebastian Aho)

The table was all set in 2015 for a draft pick that would elevate the Toronto Maple Leafs forwards. The expectation when the Leafs were on the clock at slot 24, was that the organization would take the captain of the Ottawa 67’s, Travis Konecny.

This was Toronto’s second pick of the first round.

They used the first to take Mitch Marner. Another stud player would have given the team the offensive boost they desperately needed. However, instead of taking Konecny or Sebastian Aho who were both waiting to hear their names called, General Manager Kyle Dubas traded the 24th pick to the Philadelphia Flyers for the 29th and 61st selection.

The Flyers ended up using the pick to take Konecny.

There clearly wasn’t someone Dubas coveted at the 29th position so he traded down again. This time, he sent the 29th pick to the Columbus Blue Jackets in exchange for their 34th and 68th selections.

Toronto ended up drafting defenseman Travis Dermott with the 34th pick, Jeremy Bracco with the 61st pick, and Martins Dzierkals with the 68th. While Dermott played five seasons with the Leafs and two for the Toronto Marlies in the AHL, neither Bracco nor Dzierkals ever made it to the NHL.

Konecny, meanwhile, has played seven seasons in the NHL, all of which with the Flyers.

He has experienced 488 NHL games where he has scored 141 goals and 191 assists for a total of 332 points. Aho has also played seven NHL seasons. They’ve been spent with the Carolina Hurricanes where he’s registered 468 career points in 520 games. They’ve come on 218 goals and 250 assists.

Martin Gerber

This acquisition wasn’t via trade, but it did occur at the 2009 trade deadline.

With the Toronto Maple Leafs clearly out of the playoffs as the league’s seventh worst team. Burke made a puzzling move. Though he knew and even told the media that a rebuild was necessary, the general manager claimed a goaltender off re-entry waivers from the Ottawa Senators that would help his squad improve.

The Leafs primary goalie Vesa Toskala needed to step away from the team for a hip and groin surgery.

This should have been the perfect opportunity for Toronto to allow themselves dip in the standings and look ahead to the 2009 draft. The more they lost, the better their chances were at moving up the drat order and having an opportunity to select junior hockey phenom, John Tavares.

Instead, Burke decided to go a different route. He acquired Martin Gerber, a goalie that made the team better. In 12 games, he played winning hockey for the Buds, going 6-5. One of those wins came in the final game of the season. With the Toronto Maple Leafs sitting at 79 points and 26th overall (the fifth worst record in the NHL), Gerber lifted his team to win their last game and rocket them up the standings to where they finished, at 24th.

The Leafs ended up drafting Nazem Kadri at the end of that season with the seventh pick. It was believed that Burke was trying to move up and find a trade with the New York Islanders so that the Leafs could bring Tavares to Toronto. If he had a better draft pick in his pocket, perhaps Burke may have been successful in his quest.

Roman Josi

No one embodies the the Nashville Predators like the face of their organization for 12 years, defenseman Roman Josi.

Before the surly blue liner ever played a game in the NHL, he was destined to be a member of the Maple Leafs. That was until General Manager John Ferguson Jr. pulled the trigger on a trade with the Arizona Coyotes.

Ferguson had an eye on center Yanic Perreault. In order to get him off the Coyotes, the Leafs had to give up defenseman Brendan Bell. Neither man was an impact player at the time and the swap would have been insignificant if not for the draft picks attached. The Leafs received a fifth-round pick in the 2008 NHL Entry Draft. It materialized into the Leafs making the 129th overall selection of center Joel Champagne. Champagne never made it to the NHL but spent the majority of his pro hockey career in France.

On the other side, Ferguson included Toronto’s second-round selection for the 2008 draft. That pick was later flipped by the Coyotes to the Predators for Nashville’s 2008 second and third round picks. They were used on Colby Robak (46th overall) and Mathieu Brodeur (76th overall) respectively.

Next. A List Leafs Head Coaching Candidates. dark

(Note: All statistics for this article are from Hockey Reference.)

The Preds used Toronto’s pick on Josi, making him the 38th overall selection that year. Josi has played 827 career NHL games where he’s racked up 158 goals and 443 assists for a total of 601 points. Perreault played all of 17 games for the Toronto Maple Leafs in 2007 where he potted two goals and three assists.

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