TOR Maple Leafs

The National Hockey League was formed in 1917 in Montreal by teams formerly belonging to the National Hockey Association (NHA) that had a dispute with Eddie Livingstone, owner of the Toronto Blueshirts. The owners of the other four clubs—the Montreal Canadiens, Montreal Wanderers, Quebec Bulldogs and the Ottawa Senators—wanted to replace Livingstone, but discovered that the NHA constitution did not allow them to simply vote him out of the league. Instead, they opted to create a new league, the NHL, and did not invite Livingstone to join them. They also remained voting members of the NHA, and thus had enough votes to suspend the other league's operations, effectively leaving Livingstone's league with one team.

The NHL had decided that it would operate a four-team circuit, made up of the Canadiens, Montreal Maroons, Ottawa, and one more club in either Quebec City or Toronto. Toronto's inclusion in the NHL's inaugural season was formally announced on November 26, 1917, with concerns over the Bulldogs' financial stability surfacing. The League granted temporary franchise rights to the Arena Company, owners of the Arena Gardens. The NHL granted the Arena responsibility of the Toronto franchise for only the inaugural season, with specific instructions to resolve the dispute with Livingstone or transfer ownership of the Toronto franchise back to the League at the end of the season.

The franchise did not have an official name but was informally called "the Blueshirts" or "the Torontos" by the fans and press. Although the inaugural roster was made up of players leased from the NHA's Toronto Blueshirts, including Harry Cameron and Reg Noble, the Maple Leafs do not claim the Blueshirts' history as their own. During the inaugural season, the club performed the first trade in NHL history, sending Sammy Hebert to the Senators, in return for cash. Under manager Charlie Querrie, and head coach Dick Carroll, the team won the Stanley Cup in the inaugural 1917–18 season.

For the next season, rather than return the Blueshirts' players to Livingstone as originally promised, on October 19, 1918, the Arena Company formed the Toronto Arena Hockey Club, which was readily granted full membership in the NHL. The Arena Company also decided that year that only NHL teams were allowed to play at the Arena Gardens—a move which effectively killed the NHA. Livingstone sued to get his players back. Mounting legal bills from the dispute forced the Arenas to sell some of their stars, resulting in a horrendous five-win season in 1918–19. With the company facing increasing financial difficulties, and the Arenas officially eliminated from the playoffs, the NHL agreed to let the team forfeit their last two games. Operations halted on February 20, 1919, with the NHL ending its season and starting the playoffs. The Arenas' .278 winning percentage that season remains the worst in franchise history. However, the 1919 Stanley Cup Finals ended without a winner due to the worldwide flu epidemic.

The legal dispute forced the Arena Company into bankruptcy, and it was forced to sell the team. On December 9, 1919, Querrie brokered the team's purchase by the owners of the St. Patricks Hockey Club (Percy and Fred Hambly), allowing him to maintain an ownership stake in the team. The new owners renamed the team the Toronto St. Patricks (or St. Pats for short), which they used until 1927. Changing the colours of the team from blue to green, the club won their second Stanley Cup championship in 1922. Babe Dye scored four times in the 5–1 Stanley Cup-clinching victory against the Vancouver Millionaires.

In 1924, the team's ownership changed again, as movie theatre impresario Nathan Nathanson and mining magnate Jack Bickell purchased the shares of the Hamblys. Bickell invested CA$25,000 in the St. Pats as a favour to his friend Querrie, who needed to financially reorganize his hockey team.

After several financially difficult seasons, the St. Patricks' ownership group (Querrie and Nathan Nathanson) seriously considered selling the team to C. C. Pyle for CA$200,000 (equivalent to $3,452,747 in 2023). Pyle sought to move the team to Philadelphia. However, Toronto Varsity Blues coach Conn Smythe put together a group of his own and made a $160,000 CA$160,000 (equivalent to $2,762,198 in 2023)) offer. With the support of minority shareholder Bickell, Smythe persuaded Querrie and Nathanson to accept their bid, arguing that civic pride was more important than money. Bickell would become team president.

Smythe took control on February 14, 1927; installing himself as governor and general manager. He immediately renamed the team the Maple Leafs, after the national symbol of Canada. He attributed his choice of a maple leaf for the logo to his experiences as a Canadian Army officer and prisoner of war during World War I. Viewing the maple leaf as a "badge of courage", and a reminder of home, Smythe decided to give the same name to his hockey team, in honour of the many Canadian soldiers who wore it. However, the team was not the first to use the name. A Toronto minor-league baseball team had used the name "Toronto Maple Leafs" since 1895. Although Smythe would not acquire controlling interest in the team until 1947, he would be the franchise's dominant voice for the next four decades.

Initial reports were that the team's colours were to be red and white, but the Leafs wore white sweaters with a green maple leaf for their first game on February 17, 1927. On September 27, 1927, it was announced that the Leafs had changed their colour scheme to blue and white. Although Smythe later stated he chose blue because it represents the Canadian skies and white to represent snow, these colours were also used on the trucks for his gravel and sand business. The colour blue was also a colour historically associated with the City of Toronto. The use of blue by top-level Toronto-based sports clubs began with the Argonaut Rowing Club in the 19th century, later adopted by their football team, the Toronto Argonauts, in 1873.

By 1930, Smythe saw the need to construct a new arena, viewing the Arena Gardens as a facility lacking modern amenities and seating. Finding an adequate number of financiers, he purchased land from the Eaton family, and construction of the arena was completed in five months.

The Maple Leafs debuted at their new arena, Maple Leaf Gardens, with a 2–1 loss to the Chicago Black Hawks on November 12, 1931. The opening ceremonies for Maple Leaf Gardens included a performance from the 48th Highlanders of Canada Pipe and Drums. The military band has continued to perform in every subsequent season home opening game, as well as other ceremonies conducted by the hockey club. The debut also featured Foster Hewitt in his newly constructed press box above the ice surface, where he began his famous Hockey Night in Canada radio broadcasts that eventually came to be a Saturday-night tradition. The press box was often called "the gondola", a name that emerged during the Gardens' inaugural season when a General Motors advertising executive remarked how it resembled the gondola of an airship.

By the 1931–32 NHL season, the Maple Leafs were led by the "Kid Line" consisting of Busher Jackson, Joe Primeau and Charlie Conacher and coached by Dick Irvin. The team captured their third Stanley Cup that season, vanquishing the Chicago Black Hawks in the first round, the Montreal Maroons in the semifinals, and the New York Rangers in the finals. Smythe took particular pleasure in defeating the Rangers that year. He had been tapped as the Rangers' first general manager and coach for their inaugural season (1926–27) but had been fired in a dispute with Madison Square Garden management before the season had begun.

Maple Leafs star forward Ace Bailey was nearly killed in 1933 when Boston Bruins defenceman Eddie Shore checked him from behind at full speed into the boards. Leafs defenceman Red Horner knocked Shore out with a punch, but Bailey, writhing on the ice, had his career ended. The Leafs held the Ace Bailey Benefit Game, the NHL's first All-Star Game, to collect medical funds to help Bailey. His jersey was retired later the same night. The Leafs reached the finals five times in the next seven years but bowed out to the now-disbanded Maroons in 1935, the Detroit Red Wings in 1936, Chicago in 1938, Boston in 1939 and the Rangers in 1940. After the end of the 1939–40 season, Smythe allowed Irvin to leave the team as head coach, replacing him with former Leafs captain Hap Day.

In the 1942 Stanley Cup Finals, the Maple Leafs were down three games to none in the best-of-seven series against Detroit. Fourth-line forward Don Metz then galvanized the team, to score a hat-trick in game four and the game-winner in game five. Goalie Turk Broda shut out the Wings in game six, and Sweeney Schriner scored two goals in the third period to win the seventh game 3–1, completing the reverse-sweep. The Leafs remain the only team to have successfully performed a reverse-sweep in the Stanley Cup finals. Captain Syl Apps won the Lady Byng Memorial Trophy that season, not taking one penalty, and finished his ten-season career with an average of 5 minutes, 36 seconds in penalties a season.

Smythe, who reenlisted in the Canadian Army at the outbreak of World War II, was given leave from military duty to view the final game of the 1942 finals. He arrived at the game in full military regalia. Earlier, at the outbreak of war, Smythe arranged for many of his Maple Leafs players and staff to take army training with the Toronto Scottish Regiment. Most notably, the Leafs announced a large portion of their roster had enlisted, including Apps, and Broda, who did not play on the team for several seasons due to their obligations with the Canadian Forces. During this period, the Leafs turned to lesser-known players such as rookie goaltender Frank McCool and defenceman Babe Pratt.

The Maple Leafs beat the Red Wings in the 1945 Finals. They won the first three games, with goaltender McCool recording consecutive shutouts. However, in a reversal of the 1942 finals, the Red Wings won the next three games. The Leafs were able to win the series, winning the seventh game by the score of 2–1 to prevent a complete reversal of the series played three years ago.

After the end of the war, players who had enlisted were beginning to return to their teams. With Apps and Broda regaining their form, the Maple Leafs beat the first-place Canadiens in the 1947 finals. To bolster their centre depth, the Leafs acquired Cy Thomas and Max Bentley in the following off-season. With these key additions, the Leafs were able to win a second consecutive Stanley Cup, sweeping the Red Wings in the 1948 finals. With their victory in 1948, the Leafs moved ahead of Montreal as the team having won the most Stanley Cups in League history. Apps announced his retirement following the 1948 finals, with Ted Kennedy replacing him as the team's captain. Under a new captaincy, the Leafs managed to make it to the 1949 finals, facing the Red Wings, who had finished the season with the best overall record. However, the Leafs went on to win their third consecutive Cup, sweeping the Red Wings in four games. This brought the total of Detroit's playoff game losses against the Leafs to eleven. The Red Wings were able to end this losing streak in the following postseason, eliminating Toronto in the 1950 NHL playoffs.

The Maple Leafs and Canadiens met again in the 1951 finals, with five consecutive overtime games played in the series. Defenceman Bill Barilko managed to score the series-winning goal in overtime, leaving his defensive position (despite coach Joe Primeau's instructions otherwise) to pick up an errant pass and score. Barilko helped the club secure its fourth Stanley Cup in five years. His glory was short-lived, as he disappeared in a plane crash near Timmins, Ontario, four months later. The crash site was not found until a helicopter pilot discovered the plane's wreckage plane about 80 kilometres (50 mi) north of Cochrane, Ontario 11 years later. The Leafs did not win another Cup during the 1950s, with rumours swirling that the team was "cursed", and would not win a cup until Barilko's body was found. The "curse" came to an end after the Leafs' 1962 Stanley Cup victory, which came six weeks before the discovery of the wreckage of Barilko's plane.

Their 1951 victory was followed by lacklustre performances in the following seasons. The team finished third in the 1951–52 season and was eventually swept by the Red Wings in the semi-finals. With the conclusion of the 1952–53 regular season, the Leafs failed to make it to the postseason for the first time since the 1945–46 playoffs. The Leafs' poor performance may be attributed partly to a decline in their sponsored junior system (including the Toronto St. Michael's Majors and the Toronto Marlboros). The junior system was managed by Frank J. Selke until his departure to the Canadiens in 1946. In his absence, the quality of players it produced declined. Many who were called up to the Leafs in the early 1950s were found to be seriously lacking in ability. It was only later in the decade that the Leafs' feeder clubs produced prospects that helped them become competitive again.

After a two-year drought from the playoffs, the Maple Leafs clinched a berth after the 1958–59 season. Under Punch Imlach, their new general manager and coach, the Leafs made it to the 1959 Finals, losing to the Canadiens in five games. Building on a successful playoff run, the Leafs followed up with a second-place finish in the 1959–60 regular season. Although they advanced to their second straight Cup Finals, the Leafs were again defeated by the Canadiens in four games.

Beginning in the 1960s, the Leafs became a stronger team, with Johnny Bower as the goaltender, and Bob Baun, Carl Brewer, Tim Horton and Allan Stanley serving as the Maple Leafs' defencemen. To bolster their forward group during the 1960 off-season, Imlach traded Marc Reaume to the Red Wings for Red Kelly. Originally a defenceman, Kelly was asked to make the transition to the role of centre, where he remained for the rest of his career. Kelly helped reinforce a forward group made up of Frank Mahovlich, and team captain George Armstrong. The beginning of the 1960–61 season also saw the debut of rookies Bob Nevin, and Dave Keon. Keon previously played for the St. Michael's Majors (the Maple Leafs junior affiliate), but had impressed Imlach during the Leafs' training camp, and joined the team for the season. Despite these new additions, the Leafs' 1961 playoff run ended in the semifinals against the Red Wings, with Armstrong, Bower, Kelly and others, suffering from injuries.

In November 1961, Smythe sold nearly all of his shares in the club's parent company, Maple Leaf Gardens Limited (MLGL), to a partnership composed of his son Stafford Smythe, and his partners, newspaper baron John W. H. Bassett and Toronto Marlboros president Harold Ballard. The sale price was $2.3 million (equivalent to $23,015,000 in 2023), a handsome return on Smythe's original investment 34 years earlier. Initially, Conn Smythe claimed that he knew nothing about his son's partners and was furious with the arrangement (though it is highly unlikely he could have believed Stafford could have financed the purchase on his own). However, he did not stop the deal because of it. Conn Smythe was given a retiring salary of $15,000 per year for life, an office, a secretary, a car with a driver, and seats to home games. Smythe sold his remaining shares in the company, and resigned from the board of directors in March 1966, after a Muhammad Ali boxing match was scheduled for the Gardens. Smythe found Ali's refusal to serve in the United States Army offensive, noting that the Gardens was "no place for those who want to evade conscription in their own country". He had also said that because the Gardens' owners agreed to host the fight they had "put cash ahead of class".

Under the new ownership, Toronto won another three straight Stanley Cups. The team won the 1962 Stanley Cup Finals beating the defending champion Chicago Black Hawks on a goal from Dick Duff in Game 6. During the 1962–63 season, the Leafs finished first in the league for the first time since the 1947–48 season. In the following playoffs, the team won their second Stanley Cup of the decade. The 1963–64 season saw certain members of the team traded. With Imlach seeking to reinvigorate the slumping Leafs, he made a mid-season trade that sent Duff, and Nevin to the Rangers for Andy Bathgate and Don McKenney. The Leafs managed to make the postseason as well as the Cup finals. In game six of the 1964 Cup finals, Baun suffered a fractured ankle and required a stretcher to be taken off the ice. He returned to play with his ankle frozen, and eventually scored the game-winning goal in overtime against the Red Wings. The Leafs won their third consecutive Stanley Cup in a 4–0 game 7 victory; Bathgate scored two goals.

The two seasons after the Maple Leafs' Stanley Cup victories, the team saw several player departures, including Bathgate, and Brewer, as well as several new additions, including Marcel Pronovost, and Terry Sawchuk. During the 1966–67 season, the team had lost 10 games in a row, sending Imlach to the hospital with a stress-related illness. However, from the time King Clancy took over as the head coach, to Imlach's return, the club was on a 10-game undefeated streak, building momentum before the playoffs. The Leafs made their last Cup finals in 1967. Playing against Montreal, the heavy favourite for the year, the Leafs managed to win, with Bob Pulford scoring the double-overtime winner in game three; Jim Pappin scored the series winner in Game 6. Keon was named the playoff's most valuable player and was awarded the Conn Smythe Trophy.

From 1968 to 1970, the Maple Leafs made it to the playoffs only once. They lost several players to the 1967 expansion drafts, and the team was racked with dissension because of Imlach's authoritative manner, and his attempts to prevent the players from joining the newly formed Players' Association. Imlach's management of the team was also brought into question due to some of his decisions. It was apparent that he was too loyal to aging players who had been with him since 1958. In the 1967–68 season, Mahovlich was traded to Detroit in a deal that saw the Leafs acquire Paul Henderson and Norm Ullman. The Leafs managed to return to the playoffs after the 1968–69 season, only to be swept by the Bruins. Immediately after, Stafford Smythe confronted Imlach and fired him. This act was not without controversy, with some older players, including Horton, declaring that, "if this team doesn't want Imlach, I guess it doesn't want me".

The Maple Leafs completed the 1969–70 season out of the playoffs. With their low finish, the Leafs were able to draft Darryl Sittler at the 1970 NHL Amateur Draft. The Leafs returned to the playoffs after the 1970–71 season with the addition of Sittler, as well as Bernie Parent and Jacques Plante, who were both acquired through trades during the season. They were eliminated in the first round against the Rangers.

A series of events in 1971 made Harold Ballard the primary owner of the Maple Leafs. After a series of disputes between Bassett, Ballard and Stafford Smythe, Bassett sold his stake in the company to them. Shortly afterwards, Smythe died in October 1971. Under the terms of Stafford's will, of which Ballard was an executor, each partner was allowed to buy the other's shares upon their death. Stafford's brother and son tried to keep the shares in the family, but in February 1972 Ballard bought all of Stafford's shares for $7.5 million, valuing the company at $22 million (equivalent to $157,817,000 in 2023). Six months later, Ballard was convicted of charges including fraud, and theft of money and goods, and spent a year at Milhaven Penitentiary.

By the end of 1971, the World Hockey Association (WHA) began operations as a direct competitor to the NHL. Believing the WHA would not be able to compete against the NHL, Ballard's attitude caused the Maple Leafs to lose key players, including Parent to the upstart league. Undermanned and demoralized, the Leafs finished with the fourth-worst record for the 1972–73 season. They got the fourth overall pick in the 1973 NHL Amateur Draft, and drafted Lanny McDonald. General Manager Jim Gregory also acquired the 10th overall pick from the Philadelphia Flyers, and the 15th overall pick from the Bruins, using them to acquire Bob Neely and Ian Turnbull. In addition to these first-round picks, the Leafs also acquired Borje Salming during the 1973 off-season.

Despite acquiring Tiger Williams in the 1974 draft, and Roger Neilson as head coach in the 1977–78 season, the Maple Leafs found themselves eliminated in the playoffs by stronger Flyers or Canadiens teams from 1975 to 1979. Although Neilson was a popular coach with fans and his players, he found himself at odds with Ballard, who fired him late in the 1977–78 season. Nielson was later reinstated after appeals from the players and the public. He continued as Leafs' head coach until after the 1979 playoffs, when he was fired again, alongside Gregory. Gregory was replaced by Imlach as general manager.

In the first year of his second stint as general manager, Imlach became embroiled in a dispute with Leafs' captain Darryl Sittler over his attempt to take part in the Showdown series for Hockey Night in Canada. In a move to undermine Sittler's influence on the team, Imlach traded McDonald, who was Sittler's friend. By the end of the 1979–80 season, Imlach had traded away nearly half of the roster he had at the beginning of his tenure as general manager. With the situation between Ballard and Sittler worsening, Sittler asked to be traded. Forcing the Leafs' hand, the club's new general manager, Gerry McNamara, traded Sittler to the Flyers on January 20, 1982. Rick Vaive was named the team's captain shortly after Sittler's departure.

The Maple Leafs' management continued in disarray throughout most of the decade, with an inexperienced McNamara named as Imlach's replacement in September 1981. He was followed by Gord Stellick on April 28, 1988, who was replaced by Floyd Smith on August 15, 1989. Coaching was similarly shuffled often after Nielson's departure. Imlach's first choice for coach was his former player Smith, although he did not finish the 1979–80 season after being hospitalized by a car accident on March 14, 1980. Joe Crozier was named the new head coach until January 10, 1981, when he was succeeded by Mike Nykoluk. Nykoluk was head coach until April 2, 1984. Dan Maloney returned as head coach from 1984 to 1986, with John Brophy named head coach from 1986 to 1988. Both coaches had little success during their tenure. Doug Carpenter was named the new head coach to begin the 1989–90 season when the Leafs posted their first season above .500 in the decade.

The team did not have much success during the decade, missing the playoffs entirely in 1982, 1984 and 1985. On at least two occasions, they made the playoffs with the worst winning percentages on record for a playoff team. However, in those days, the top four teams in each division made the playoffs, regardless of record. Since the Norris only had five teams in total, this meant only the last-place team in the division missed the postseason. In 1985–86, for instance, they finished with a .356 winning percentage, the fourth worst in the league. However, due to playing in a Norris Division where no team cracked the 90-point mark, the Leafs still made the playoffs because Detroit had the worst record in the league. In 1987–88, they entered the final day of the season with the worst record in the league, but were only one point behind the Minnesota North Stars and thus were still in playoff contention. The Red Wings was the only team in the division with a winning record. However, the Leafs upset the Red Wings in their final game while the North Stars lost to the Flames hours later to hand the Leafs the final spot from the Norris.

The low finishes allowed the team to draft Wendel Clark first overall at the 1985 NHL Entry Draft. Clark managed to lead the Leafs to the playoffs from 1986 to 1988, as well as the 1990 playoffs. Ballard died on April 11, 1990.

Don Crump, Don Giffin, and Steve Stavro were named executors of Ballard's estate. Stavro succeeded Ballard as chairman of Maple Leaf Gardens Ltd. and governor of the Maple Leafs. Cliff Fletcher was hired by Giffin to be the new general manager, although this was opposed by Stavro, who told Fletcher that he wanted to appoint his own general manager.

Notwithstanding Stavro's initial reluctance with Fletcher's appointment, the Leafs' new ownership would soon earn a reputation for steering clear of exerting undue interference in hockey operations, in stark contrast to Ballard. Fletcher soon set about building a competitive club, hiring Pat Burns as the new coach, and making a series of trades and free-agent acquisitions, such as acquiring Doug Gilmour and Dave Andreychuk, which turned the Leafs into a contender. Assisted by stellar goaltending from minor league call-up Felix Potvin, the team posted a then-franchise-record 99 points.

Toronto dispatched the Detroit Red Wings in seven games in the first round, then defeated the St. Louis Blues in another seven games in the Division Finals. Hoping to meet long-time rival Montreal (who was playing in the Wales Conference finals against the New York Islanders) in the Cup finals, the Leafs faced the Los Angeles Kings in the Campbell Conference finals. They led the series 3–2 but dropped game six in Los Angeles. The game was not without controversy, as Wayne Gretzky clipped Gilmour in the face with his stick, but referee Kerry Fraser did not call a penalty, and Gretzky scored the winning goal moments later. The Leafs eventually lost in game seven 5–4.

The Leafs had another strong season in 1993–94, starting the season on a 10-game winning streak, and finishing it with 98 points. The team made it to the conference finals again, only to be eliminated by the Vancouver Canucks in five games. At the 1994 NHL Entry Draft, the Leafs packaged Wendel Clark in a multi-player trade with the Quebec Nordiques that landed them Mats Sundin. Missing two consecutive playoffs in 1997 and 1998, the Leafs relieved Fletcher as general manager.

On February 12, 1998, MLGL purchased the Toronto Raptors, a National Basketball Association franchise, and the arena the Raptors were building, from Allan Slaight and Scotiabank. With the acquisition, MLGL was renamed Maple Leaf Sports & Entertainment (MLSE), acting as the parent company of the two teams. Larry Tanenbaum was a driving force in the acquisition, having bought a 12.5 percent stake in Maple Leaf Gardens Limited (MLGL) in 1996.

Curtis Joseph was acquired as the team's starting goalie, while Pat Quinn was hired as the head coach before the 1998–99 season. Realigning the NHL's conferences in 1998, the Leafs were moved from the Western to the Eastern Conference. On February 13, 1999, the Leafs played their final game at the Gardens before moving to their new home at the then-Air Canada Centre. In the 1999 playoffs, the team advanced to the Conference Finals but lost in five games to the Buffalo Sabres.

In the 1999–2000 season, the Leafs hosted the 50th NHL All-Star Game. By the end of the season, they recorded their first 100-point season and won their first division title in 37 years. In both the 2000 and 2001 playoffs, the Leafs defeated the Ottawa Senators in the first round and lost to the New Jersey Devils in the second round. In the 2002 playoffs, the Leafs dispatched the Islanders and the Senators in seven games each during the first two rounds, only to lose to the Cinderella-story Carolina Hurricanes in six games in the Conference Finals. The 2001–02 season was particularly impressive in that injuries sidelined many of the Leafs' better players, but the efforts of depth players, including Alyn McCauley, Gary Roberts and Darcy Tucker, led them to the Conference Finals.

As Joseph opted to become a free agent during the 2002 off-season, the Leafs signed Ed Belfour as the new starting goaltender. Belfour played well during the 2002–03 season and was a finalist for the Vezina Trophy. The Leafs lost to Philadelphia in seven games during the first round of the 2003 playoffs. In 2003, an ownership change occurred in MLSE. Stavro sold his controlling interest in MLSE to the Ontario Teachers' Pension Plan (OTPP) and resigned his position as chairman in favour of Tanenbaum. Quinn remained as head coach but was replaced as general manager by John Ferguson Jr.

Before the 2003–04 season, the team held their training camp in Sweden and played in the NHL Challenge against teams from Sweden and Finland. The Leafs went on to enjoy a very successful regular season, leading the NHL at the time of the All-Star Game (with Quinn named head coach of the East's All-Star Team). They finished the season with a then-franchise-record 103 points. They finished with the fourth-best record in the League, and their highest overall finish in 41 years, achieving a .628 win percentage, their best in 43 years, and third-best in franchise history. In the 2004 playoffs, the Leafs defeated the Senators in the first round of the postseason for the fourth time in five years, with Belfour posting three shutouts in seven games, but lost to the Flyers in six games during the second round.

Following the 2004–05 NHL lockout, the Maple Leafs experienced their longest playoff drought in the team's history. They struggled in the 2005–06 season; despite a late-season surge (9–1–2 in their final 12 games), led by goaltender Jean-Sebastien Aubin, Toronto was out of playoff contention for the first time since 1998. This marked the first time the team had missed the postseason under Quinn, who was later relieved as head coach. Quinn's dismissal was controversial since many of the young players who were key contributors to the Leafs' late-season run had been drafted by him before Ferguson's arrival, while Ferguson's signings (Jason Allison, Belfour, Alexander Khavanov, and Eric Lindros) had suffered season-ending injuries.

Paul Maurice, who had previously coached the inaugural season of the Maple Leafs' Toronto Marlies farm team, was named as Quinn's replacement. On June 30, 2006, the Leafs bought out fan-favourite Tie Domi's contract. The team also decided against picking up the option year on goaltender Ed Belfour's contract; he became a free agent. However, despite the coaching change, as well as a shuffle in the roster, the team did not make the playoffs in 2006–07. During the 2007–08 season, John Ferguson Jr. was fired in January 2008 and replaced by former Leafs' general manager Cliff Fletcher on an interim basis. The team retained Toronto-based sports lawyer Gord Kirke to begin a search for a new team president and general manager, and negotiate a contract. The Leafs did not qualify for the postseason, marking the first time since 1928 the team had failed to make the playoffs for three consecutive seasons. It was also Sundin's last year with the Leafs, as his contract was due to expire at the end of the season. However, he refused Leafs management's request to waive his no-trade clause for the team to rebuild by acquiring prospects or draft picks. On May 7, 2008, after the 2007–08 season, the Leafs fired Maurice, as well as assistant coach Randy Ladouceur, naming Ron Wilson as the new head coach, and Tim Hunter and Rob Zettler as assistant coaches.

On November 29, 2008, the Maple Leafs hired Brian Burke as their 13th non-interim, and the first American, general manager in team history. The acquisition ended the second Cliff Fletcher era and settled persistent rumours that Burke was coming to Toronto. On June 26, 2009, Burke made his first appearance as the Leafs GM at the 2009 NHL Entry Draft, selecting London Knights forward Nazem Kadri with the seventh overall pick. On September 18, 2009, Burke traded Toronto's first- and second-round 2010, as well as its 2011 first-round picks, to the Boston Bruins in exchange for forward Phil Kessel. On January 31, 2010, the Leafs made another high-profile trade, this time with the Calgary Flames in a seven-player deal that brought defenceman Dion Phaneuf to Toronto. On June 14, during the off-season, the Leafs named Phaneuf captain after two seasons without one following Sundin's departure. On February 18, 2011, the team traded long-time Maple Leafs defenceman Tomas Kaberle to the Bruins in exchange for prospect Joe Colborne, Boston's first-round pick in 2011, and a conditional second-round draft choice.

On March 2, 2012, Burke fired Wilson and named Randy Carlyle the new head coach. However, the termination proved to be controversial as Wilson had received a contract extension just two months before being let go. Changes at the ownership level also occurred in August 2012, when the OTPP completed the sale of their shares in MLSE to BCE Inc. and Rogers Communications. On January 9, 2013, Burke was fired as general manager, and replaced by Dave Nonis. In their first full season under the leadership of Carlyle, Toronto managed to secure a playoff berth in the 2012–13 season (which was shortened again due to another lock-out) for the first time in eight years. However, the Leafs lost in seven games to eventual 2013 Stanley Cup finalist Boston in the first round. Despite the season's success, it was not repeated during the 2013–14 season, as the Leafs failed to make the playoffs.

Following the 2013–14 regular season, Brendan Shanahan was named as the president and an alternate governor of the Maple Leafs. On January 6, 2015, the Leafs fired Randy Carlyle as head coach, and assistant coach Peter Horachek took over on an interim basis immediately. While the Leafs had a winning record before Carlyle's firing, the team eventually collapsed. On February 6, 2015, the Leafs set a new franchise record of 11 consecutive games without a win. At the beginning of February, Shanahan gained the approval of MLSE's board of directors to begin a "scorched earth" rebuild of the club. Both Dave Nonis and Horachek were relieved of their duties on April 12, just one day after the season concluded. In addition, the Leafs also fired several assistant coaches, including Steve Spott, and Rick St. Croix; as well as individuals from the Leafs' player scouting department.

On May 20, 2015, Mike Babcock was named as the new head coach, and on July 23, Lou Lamoriello was named the 16th general manager in team history. On July 1, 2015, the Leafs packaged Kessel in a multi-player deal to the Pittsburgh Penguins in return for three skaters, including Kasperi Kapanen, a conditional first-round pick, and a third-round pick. Toronto also retained $1.2 million of Kessel's salary for the remaining seven seasons of his contract. During the following season, on February 9, 2016, the Leafs packaged Phaneuf in another multi-player deal, acquiring four players, as well as a 2017 second-round pick from the Ottawa Senators. The team finished last in the NHL for the first time since the 1984–85 season. They subsequently won the draft lottery and used the first overall pick to draft Auston Matthews.

In their second season under Babcock, Toronto secured the final Eastern Conference wildcard spot for the 2017 playoffs. On April 23, 2017, the Maple Leafs were eliminated from the playoffs by the top-seeded Washington Capitals four games to two in the best-of-seven series.

Toronto finished the 2017–18 season with 105 points by beating Montreal 4–2 in their final game of the regular season, a franchise-record, beating the previous record of 103 points set in 2004. They faced the Boston Bruins in the First Round and lost in seven games. Following the playoffs, Lamoriello was not renewed as general manager. Kyle Dubas was subsequently named the team's 17th general manager in May 2018. During the 2018 off-season, the Maple Leafs signed John Tavares to a seven-year, $77 million contract. On April 1, the Maple Leafs clinched a division berth for the 2019 Stanley Cup playoffs. The Maple Leafs were eliminated in the First Round of the 2019 playoffs on April 23, after losing to the Bruins in a seven-game series.

On October 2, 2019, Tavares was named as the team's 25th team captain prior to the Leafs' 2019–20 season opening game. After a 9–10–4 start to the 2019–20 season, the club relieved Babcock as head coach on November 20, with Sheldon Keefe named as his replacement. The Maple Leafs were eliminated in the 2020 Stanley Cup Qualifiers on August 9, after losing a five-game series against the Columbus Blue Jackets.

Due to the COVID-19 pandemic and travel restrictions at the Canada–United States border, the Leafs were temporarily moved to the North Division for the 2020–21 season alongside the NHL's other Canadian teams. During that season, teams only played games against teams in their divisions, in a limited 56-game season. On May 8, 2021, the Leafs clinched the North Division title, giving the Leafs guaranteed home advantage in the first two rounds of the 2021 Stanley Cup playoffs. Matthews also led the league in goals with 41 goals, becoming the first Maple Leaf to win the Maurice "Rocket" Richard Trophy. However, the Leafs lost in the First Round to their rivals, the Montreal Canadiens, with the Leafs surrendering a 3–1 series lead in the process.

Despite the ending to the previous season, the Leafs were poised to make another run, with much of the core roster intact. Aided by the arrival of defenceman Mark Giordano and centre Colin Blackwell from the Seattle Kraken on March 21, the team cruised throughout the regular season. The Maple Leafs broke their franchise record for points in a season, with 115, and wins in a season, with 50, during a 4–2 victory over the New York Islanders on April 17. Despite the achievement, they were unable to match the league-leading Florida Panthers', finishing second in the Atlantic Division During the season, Matthews became the first Leaf in a decade to score 60 goals in a season, and was awarded the Hart Memorial Trophy. The Leafs made the playoffs but lost in the First Round to the Tampa Bay Lightning in seven games. With this loss, the Maple Leafs became the first team in the four major North American sports leagues to lose five consecutive winner-take-all games.

The 2022 off-season saw the departure of the Leafs' goalie tandem, Jack Campbell and Petr Mrazek, the former signing with Edmonton, the latter being traded to the Blackhawks during the 2022 NHL Draft. Needing a goaltender tandem for the upcoming season, the Leafs acquired Matt Murray through a trade with the Senators, and signed free agent Ilya Samsonov.

During the 2022–23 NHL season, the Leafs again fared well in the regular season, achieving an excellent 50–21–11 record and 111 points, one point less than the record achieved the season prior. However, the record-setting Boston Bruins led the division, finishing with 135 points, and leaving the Leafs in second place in the Atlantic. In the First Round of the playoffs, the Leafs defeated the Lightning in a six-game series, marking the first time the Maple Leafs advanced to the second round of the playoff appearance since 2004. During the series with the Lightning, the Leafs became the first NHL team to win three road playoff games in overtime. However, the Leafs lost to the Florida Panthers in the second round in five games. Following the loss, Dubas' contract as general manager was not renewed with the club for the 2023–24 season. Dubas was then replaced by Brad Treliving on May 31.

In 2023–2024, the team finished with a 46–26–10 record, good for 102 points and the third seed in the Atlantic Division. Matthews broke his own career and franchise records for goals in a season, with 69, and was awarded his third Rocket Richard Trophy. However, they were again eliminated in the first round of the playoffs, falling to the Bruins in seven games. After the season, Keefe was dismissed as head coach on May 9, with Craig Berube hired as his successor on May 17.

Prior to the 2024–25 season, Tavares relinquished his role as captain to Matthews on August 14, 2024, with the latter becoming the 26th overall and first American-born captain in franchise history.