Top 10 Best UFA Signings in Toronto Maple Leafs History

Free Agency can make or break a season and the Toronto Maple Leafs have a long history of signings.

We went over the worst five UFA signings in team history, but for this experiment we’ll be going through the top 10 Toronto Maple Leafs UFA signings instead.

More often than not, that flashy free agent at the top of everybody’s list doesn’t work out as planned.

One, they’re overpaid because teams are desperate, and two, they just can’t live up to expectations for a seven or eight-year contract.

The best free agent signings are usually those that have short-term (1-3 years) and don’t break the bank.

Finding a player that’s an aging veteran on the cheap, or a young player who has lots to prove is where you find value and the Leafs know all about this.

Throughout Leafs history, there have been times where the Leafs find a diamond in the rough, but there’s also been times where they pay David Clarkson over $35 million for seven years.

You can’t throw away money anymore during free agency because every dollar is so important in a salary-cap world.

As we go through this list, you’ll see a ton of great signings in the late 1990s and early 2000s because there was no salary cap then and the Leafs had the capability of being big-spenders.

Let’s look at the top-10 best UFA signings in team history.

#10. Patrick Marleau

During the Free Agency period in summer, 2017, Leafs fans saw plenty of optimism. Their team had just made the playoffs for the first time since 2004 in a full 82-game regular season and with stars Auston Matthews, William Nylander and Mitch Marner only going to improve, it was a special time in Leafs Nation.

As a result, as free agency hit, everyone expected the team to sign a defenseman. The offense seemed intact, but a defenseman was something the team desperately needed.

Instead, Lou Lamoriello and company decided to sign Patrick Marleau to a three-year $18.75 million contract.

Although Marleau only played out two of those three years and the team needed to trade a first-round draft pick to get out of the contract, the deal was worth it. Marleau scored 27 goals in his first year and provided a veteran presence in the dressing room that you can’t buy.

Marleau’s contract was definitely too rich by the end of it, but he was still a very good second-line player and leader that Matthews and Marner adored.

#9. Tyler Bozak

It’s crazy to think that Bozak was never drafted to the National Hockey League.

Even after scoring 45 goals and 128 points in his final year of junior, no NHL team came knocking so Bozak decided to go play NCAA hockey instead.

After two seasons at the University of Denver, the Leafs signed Bozak as an undrafted free agent.

One of the best moves that Brian Burke ever made as General Manager.

Although Bozak was always asked to play a bigger role than he was capable of, he became a fan-favorite quickly.

Bozak provided a number of highlights over the years that will always be remembered.

His shootout winner in the 2014 Winter Classic always comes to mind, but his most notable highlight was his OT goal in Game 3 of the 2017 NHL Playoffs against Washington.

It’s unfortunate that Bozak was never able to play a role more suited to his game in Toronto, because as we saw with the St. Louis Blues last season, Bozak can be a third-line centre on a Stanley Cup winning team.

#8. Steve Thomas

Steve “Stumpy” Thomas is a unique individual to this list, because he actually fits our criteria twice.

The Leafs originally signed Thomas as undrafted free agent in 1984, then they signed him again in 1998 near the end of his career. In NHL history, I’m sure there’s not too many players that can say a team signed them twice as a Free Agent.

However, let’s start at the beginning of Thomas’ career. Similar to Bozak, if you look back at his career, it’s crazy to think that he was never drafted. He finished his career with 1235 games played and 933 points, and although he’s not currently in the Hockey Hall-of-Fame, many believe he should be.

During his first stint in Toronto, Thomas showed pretty quickly that he had NHL capable talent. He scored 20 goals in his first full season, then followed that up with 37 in his second season.

Although the Leafs weren’t able to hold onto him for any longer than that, Thomas continued his scoring ways when he returned to the team in 1998. In two seasons he scored 28 and 26 goals respectively and seemed to score every other game in the Leafs playoffs run those two years.

#7. Joe Nieuwendyk

The signing of Nieuwendyk is one similar to Marleau.

Although Marleau’s career wasn’t as decorated with Stanley Cup’s as Nieuwendyk’s was, in both instances, the Leafs were signing a Hall-of-Fame veteran trying to get a last chance at winning.

When Nieuwendyk had arrived in Toronto, he had done everything a player dreams of in an NHL career. He’d won a Conn Smythe and three Stanley Cups with three different teams.

However, the only thing missing was the chance at winning a fourth Stanley Cup in his hometown.

The fondest memory of Nieuwendyk will always be during the 2004 NHL Playoffs in Game 7 against the Ottawa Senators.

Streaking through the left-wing, Nieuwendyk scored two identical goals against Patrick Lalime that secured the series win for Toronto and sent them to the second round.

Although the Leafs were unable to win the Stanley Cup in the one season that Nieuwendyk played in Toronto, he provided great leadership and was a tremendous player that season.

#6. Gary Roberts

There’s nothing better than seeing a hometown kid sign with Toronto and be successful, and that’s just what Roberts did.

Roberts wasn’t going to be the 50-goal scorer he once was in Calgary when he signed in Toronto, but his leadership and toughness was something that would make him so valuable.

The 2001-2002 season will most likely be the year that Leafs fans remember Roberts most for. Roberts had 21 goals in the regular season, which was fourth on the team, but it was his playoff performance that year that fans started to adore him for.

Robert’s Triple-OT winner in the 2002 Playoffs against Ottawa was one of the most famous goals in recent playoff history.

That goal was one of seven he would score in the 2002 Stanley Cup playoff-run, as he led the Leafs to the Eastern Conference Finals against his old team; the Carolina Hurricanes.

After an injury limited Mats Sundin to only eight games that playoff-run, Roberts became the leader on-and-off the ice and was the reason why the Leafs went so far, ultimately losing in the Eastern Conference Finals.

Roberts is one of the most beloved in Toronto Maple Leafs in team history.

#5. Alexander Mogilny

When Alexander Mogilny was on, he was one of the most lethal players in the NHL.

Mogilny’s 1992-93 season in Buffalo will go down as one of the best goal scoring seasons in history. With 76 goals in 77 games, there’s a small chance that any player will come close to that mark any time soon.

Although the Leafs signed Mogilny at the tail-end of his career, he still had tremendous talent. Paired up with Mats Sundin most nights, “Al-Mo” and Sundin were an unstoppable combination as the team made it to the Eastern Conference Finals during his first season in Toronto.

In Mogilny’s first two seasons with the Leafs, he scored 24 and 33 goals. His second season of 33 goals came with 46 assists for a total of 77 points, which led the team.

Besides Mogilny and Sundin, there wasn’t a ton of offense during his second season as they were the only players with more than 16 goals on the season, so they essentially carried the team into the playoffs that year.

Registering over a point-per game in his career, an Olympic Gold medal, World Championship Gold medal and Stanley Cup championship, it’s a shock that Mogilny is yet to be inducted into the Hockey Hall-of-Fame.

#4. Ed Belfour

Belfour had big shoes to fill taking over the goaltending job from Curtis Joseph, who left for Detroit that off-season, but he was up for the task.

Prior to joining the Toronto Maple Leafs, Belfour had won every award a goalie dreams of and quickly became a fan-favorite in Toronto.

Belfour’s trophy case included: one Calder Trophy, two Vezina Trophies, three William Jennings Trophies and a Stanley Cup.

The only thing missing for the Carman, Manitoba native was a Stanley Cup with an ‘Original Six’ team.

During his time in Toronto, Belfour proved that he was still one of the best goaltenders in the NHL. In his first two seasons with the Leafs, he averaged a 0.920 SV % and 2.19 GAA.

Although the team failed to win a Stanley Cup, Belfour provided a number of playoff highlights that fans still remember.

His 72-save performance during Game 4 of the 2003 NHL playoffs against Philadelphia will live on forever. Although the Leafs ended up losing the game in Triple-OT, that night is one of the most remarkable goaltender acts in NHL history.

#3. Curtis Joseph

After a great career in St. Louis and Edmonton, ‘Cujo’ decided to sign with his hometown Leafs in 1998.

After missing the playoffs for the last two seasons, the Joseph signing couldn’t have happened at a better time. The Leafs never missed the playoffs in his four years with Toronto and ultimately made it to the Eastern Conference Finals two times in that stretch.

Fans fell in love with Joseph immediately as he finished runner-up to Dominik Hasek for the Vezina Trophy in his first season in Toronto.

The story of Joseph is a tough-tale and the fact that he even made it to the NHL was a miracle. As displayed in his book ‘Cujo: The Untold Story of My Life’, Joseph’s childhood was filled with neglect and overcoming the obstacles that he did was remarkable.

Despite his tough upbringing, in terms of goaltenders in Leafs history, Cujo is easily one of the top-five best goaltenders to ever play for the organization.

Similar to Mogilny, it’s a shock that he’s yet to be inducted into the Hockey Hall of Fame because he’s currently seventh among all goaltenders with 454 career wins.

#2. John Tavares

It took a seven-year $77 million contract, but the Leafs finally signed that All-Star centre they’d been dreaming about for years.

After missing out on the likes of Steven Stamkos and Brad Richards, it’d been a while since the Leafs signed a marquee UFA.

However, the time finally arrived when John Tavares wanted to come home and play for his favorite team growing up.

In 11 seasons, Tavares has never had a year where he’s scored less than 24 goals in a season. That even includes two seasons where he only played 48 and 59 games.

The current captain of the Leafs is one of the top players in the NHL and has been as consistent as almost anyone else in the league over the past decade.

In his first season with Toronto, Tavares displayed no nerves scoring a career high 47 goals and 88 points. Although his second season has regressed, he’s still on pace for 33 goals and 80 points if the season were to continue.

It’ll be interesting to see how the next five years plays out from his monster contract, but Tavares doesn’t seem like a player who will slow down.

The future Hall-of-Famer wants nothing more than to bring a Stanley Cup home and it wouldn’t be shocking if his number ’91’ is retired by Toronto at the end of his career.