When you think top passionate hockey cities in the NHL, two that will always rise to the top are Toronto and Philadelphia. The on-ice rivalry between the two has gone through hot and cold periods during their history, with the last spike coming in the 2004 postseason when the Flyers eliminated the Maple Leafs in the second round. It was the last time the Leafs would make the playoffs for eight years, and the second straight year the Flyers sent them packing from the postseason. Until the dawn of the new millennium, the teams were regular trade partners, though have kept their distance over the last two decades.
9/1/67 – Al Millar for cash
This was the very first trade in Flyers history. Al Millar was a goaltender who spent a majority of his career in the minors. He was under contract to the Leafs, but never actually played for them. The Flyers acquired him and sent him to the AHL where he had 33 starts with the Quebec Aces, but never played for the Flyers. He’d retire from hockey two years later.
3/2/69 – Gerry Meehan, Mike Byers, Bill Sutherland for Brit Selby, Forbes Kennedy
Gerry Meehan was a forward who played most notably with the Buffalo Sabres in the 1970’s, a team he’d later become the general manager of. He played 12 games with the Flyers to finish out the 1968-69 season, but left during the offseason.
Mike Byers was a depth forward who bounced between the AHL and NHL. He played five games with the Flyers in 1968-69, and spent the entire 1969-70 season with their AHL affiliate the Quebec Aces. He’d leave in free agency during the 1970 offseason, ultimately signing with the Los Angeles Kings.
Bill Sutherland was actually an original Flyer, scoring the first goal in franchise history. He was lost to the North Stars during the 1967 intra-league draft and was immediately dealt to Toronto. He’d play just 44 games for the Leafs before being reacquired by the Flyers in this trade.
Brit Selby starter his career with the Leafs before spending time in Vancouver and Philadelphia. He’d play 99 games during his return to Toronto over parts of the next three seasons before being traded to St. Louis in 1970.
Forbes Kennedy was an original Flyer and helped create the “Broad Street Bullies” mentality with his 325 penalty minutes in 132 games in Philly. He was dealt to Toronto where he’d only play in 13 games before getting in a brawl where he punched out a referee, ultimately getting suspended and ending his tenure with the club. He’d retire from hockey soon after.
1/31/71 – Bruce Gamble, 1971 first round pick (Pierre Plante) for Bernie Parent and 1971 second round pick (Rick Kehoe)
This trade was part of a three-way deal that also involved the Boston Bruins. Mike Walton was shipped from Boston to Toronto and the Flyers acquired Rick MacLeish and Danny Schock as part of the deal for being the liaison between the two.
Parent was the starter upon his arrival to Philly splitting time with Doug Favell for four seasons, but they wanted to bolster the offense and dealing him to Toronto where he formed a tandem with his hero Jacques Plante. He learned to become a much better, technically proficient goaltender. He’d play two seasons in Toronto and one season with the WHA Blazers after the trade before returning to Philly to lead them to back-to-back Stanley Cups
The Leafs also drafted Rick Kehoe, who’d spend three seasons in Toronto before a trade sent him to Pittsburgh where he’d win two Stanley Cups, ultimately ending up in the Penguins’ Hall of Fame.
The Flyers landed goaltender Bruce Gamble, who became the backup for much of the following two seasons. A heart attack suffered mid-game in February of 1972 forced his retirement. He would pass away from a second heart attack after practicing for a men’s league game a decade later.
Philly drafted forward Pierre Plante in the first round of 1971. He spent two seasons in the Flyers’ organization, mainly in the AHL, before being traded to St. Louis in the 1977 offseason.
5/15/73 – Bernie Parent rights, 1973 second round pick (Larry Goodenough) for Doug Favell, 1973 first round pick (Bob Neely)
Parent ended up in a contract dispute with the Leafs just two years after being acquired and ultimately became the first NHL player to jump ship to the World Hockey Association. He played one season with the Philadelphia Blazers. Another contract dispute in the WHA forced him to leave the league and return to the NHL, but he still refused to sign with the Leafs. Toronto traded his rights back to the Flyers along with a second round pick for his tandem partner Doug Favell and a 1973 first round pick.
Parent’s return to Philadelphia was an example of some of the best goaltending of the era. He’d win two Vezina Trophies, two Conn Smythe Trophies and be a runner-up for the Hart Trophy in 1974 as he backstopped the Flyers to back-to-back Stanley Cups.
The Flyers also drafted defenseman Larry Goodenough, who played parts of three seasons with the club from 1975 to 1977.
Doug Favell played two-and-a-half seasons with the Leafs but wasn’t able to replicate the success he had in Philadelphia. They also drafted forward Bob Neely, who played all five of his NHL seasons with the Leafs, posting 98 points in 283 games.
5/23/73 – cash for Willie Brossart
Willie Brossart was the Flyers’ third round pick in 1969 and played 49 games with the Flyers over parts of three seasons, mainly spending time in the AHL. He was traded to the Leafs for cash, though only played 21 games for them before once again being traded, this time to the Washington Capitals.
5/27/74 – Dave Fortier, Randy Osburn for Bill Flett
Flett came out of the gate hot in his career with the LA Kings, but dwindling production forced him out of Los Angeles and he landed in Philadelphia. He had a career year in 1972-73 with 43 goals and 74 points. He was part of the 1974 Cup team. Flett was traded to the Leafs during the offseason for a pair of prospects. Flett would play one season in Toronto before they placed him on waivers where he was claimed by the Atlanta Flames.
Dave Fortier was a defense prospect who played 23 games for the Leafs. He was claimed by the Islanders in an Intra-League Draft just two weeks after this trade. Randy Osburn played one game for the Flyers after the trade, spending the next four seasons in the minor leagues.
1/20/82 – Darryl Sittler for Rich Costello, Ken Strong, 1982 second round pick (Peter Ihnacak)
Sittler was a 12-year veteran and Maple Leafs legend by the time 1982 rolled around. His last few seasons in Toronto were a bit tumultuous to say the least. Sittler stripped himself of the captaincy after he felt his communication with management deteriorated to the point of no return. The traded his best friend Lanny McDonald to the Colorado Rockies and in response he offered to waive his no trade clause to go to Philadelphia or the Minnesota North Stars.
Sittler was ultimately dealt to the Flyers where he’d play three seasons
The Leafs got forward Rick Costello, who was the Flyers’ 37th overall pick in 1981. He’d play just 12 NHL games for Toronto, spending the rest of his four year stint with the organization in the AHL. They drafted Slovak forward Peter Ihnacak 25th overall in 1982 and he’d spend eight seasons with the Leafs, the only NHL team he’d play for.
Ken Strong was the Flyers’ third round pick in 1982 and was originally a “future consideration” as part of the deal. He only suited up for 15 games with the Leafs before returning to his native Austria to finish his career.
1/11/83 – Michel Larocque for Rick St. Croix
Larocque was a goaltender best know for his long stint with the Canadiens in the 1970’s. He only played two games upon his arrival in Philly, as the crease was already full with Pelle Lindbergh and Bob Froese.
Rick St. Croix was the Flyers’ longtime third string goaltender that Laroque would ultimately replace. He would play 48 NHL games with the Leafs, but spent a bulk of the next few seasons in the AHL.
12/4/87 – 1989 fifth round pick (Pat MacLeod) (traded to North Stars) for Mike Stothers
Mike Stothers was the Flyers’ 21st overall pick in 1980 and spent seven seasons with the organization, mainly in the AHL. He played the remainder of the 1987-88 season with the Leafs, both in the NHL and AHL, then returned to the Hersey Bears of the AHL for the last four seasons of his career.
The Flyers landed a 1989 fifth round pick in return for Sothers. The pick was traded 369 days later to the Minnesota North Stars in exchange for defenseman Moe Mantha, who would play 31 games with the Flyers before being claimed by Winnipeg during the 1989 Waiver Draft.
6/21/88 – Mike Stothers for Bill Root
Mike Stothers was originally the Flyers’ first round pick in 1980 and played with the organization until 1988, mainly in the AHL. He was dealt to the Leafs in December of 1987. He was reacquired by the Flyers in this trade during the following offseason and spent the next four seasons solely in the AHL before hanging up the skates in 1992.
Bill Root was a journeyman defenseman during his six NHL seasons and landed in Philly after being claimed on waivers from St. Louis in November of 1987. Root, who had played three seasons in Toronto from 1984 to 1987, never suited up for the NHL squad upon his return, rather spending three seasons in the AHL before retiring from hockey.
2/7/89 – Al Secord for 1989 fifth round pick (Keith Carney)
Al Secord is best known for his tenure with the Blackhawks throughout the 1980’s, but spent a year-and-a-half in Toronto after his time in Chicago came to an end. He was acquired by the Flyers for their 1989 playoff push when he had one goal and five points in 35 regular season and playoff contests. He was not re-signed in the offseason and returned to Chicago in the summer of 1989.
The Leafs drafted defenseman Keith Carney 96th overall in 1989 but never played for the organization, retiring shortly after his college career came to an end.
3/6/89 – Ken Wregget for 1989 first round pick (Rob Peterson), 1989 first round pick (Steve Bancroft)
The Maple Leafs had an abundance of goaltenders in 1989 and the Flyers needed a solid option to tandem with Ron Hextall. The Flyers offered up a pair of first round picks for Wregget, and he played a lion’s share of the time during the 1989-90 season. He’d play two more seasons as a backup, but the emergence of Dominic Roussel made Wregget expandable and he was traded to the Penguins where he’d win a Stanley Cup in 1992.
The Leafs drafted forward Rob Pearson 12th overall and played three seasons with the team. He amassed 458 penalty minutes in 192 games in Toronto.
Bancroft was drafted 21st overall and played defense. He was a long-time journeyman, never playing for the Leafs, though did eventually play six NHL games with the Blackhawks and Sharks.
8/28/89 – rights to Jiri Latal for 1991 seventh round pick (Traded to PHI) (Andre Lomakin)
Jiri Latal was a defenseman with his star on the rise in his native Czech Republic. When the Velvet Revolution took place and players could easily make the jump to North America, the Flyers acquired his rights from Toronto, who they originally drafted in 1985, in hopes they found a new top defenseman.
Latal spent three seasons in North America, all of which with the Flyers where he had 48 points in 92 games. A myriad of injuries prevented him from ever reaching his lofty ceiling.
The Leafs would trade the pick back to the Flyers 11 days later.
9/8/89 – 1991 fifth round pick (traded to WPG) (Juha Ylonen), 1991 seventh round pick (Andre Lomakin) for Mark Laforest
11 days after their last deal, the Flyers and Leafs made yet another trade, this time swapping a depth goalie for a pair of draft picks.
Mark Laforest had played two seasons with the Flyers organization bouncing between the NHL and AHL, picking up the few NHL starts Ron Hextall didn’t. He played one season in Toronto, only seeing 27 NHL starts. He’d join the Rangers organization the following year.
The Flyers drafted forward Andre Lomakin, who played two seasons in Philadelphia, tallying 50 points in 108 games before being drafted by the Panthers in the 1993 expansion.
The Flyers traded the 1991 fifth round pick to the Jets in exchange for Keith Acton and Pete Peeters in October of 1989.
6/16/90 – 1990 third round pick (Al Kinisky) for Kevin Maquire, 1991 eighth round pick (Dmitri Mironov)
The Flyers acquired Kevin Maquire at the 1990 NHL trade deadline and he played five games for the club. He was dealt to the Leafs on draft day in 1990 along with an eighth round pick in exchange for a third round pick. He would play parts of two seasons with the club before retiring and pursuing a career as a referee.
The Leafs drafted Dmitri Mironov in the eighth round in 1991. He’d play three seasons in Toronto, eventually winning a Stanley Cup with the Red Wings in 1998.
The Flyers drafted forward Al Kinisky in the third round of the 1990 draft, but he’d never play hockey beyond his junior career which came to an end in 1993.
7/29/91 – 1993 third round pick (Vinny Prospal) for rights to Mike Bullard
Mike Bullard was a long-time Pittsburgh Penguin during the 1980’s and bounced around the league quite a bit later in his career. He played 124 games with the Flyers from 1988 to 1990 recording 113 points.
Bullard played the 1990-91 season in Switzerland and his rights were traded to the Maple Leafs. He returned to North America for one season, scoring 28 points in 65 games with the Leafs before returning to Europe where he’s spend another decade before retiring.
The Flyers drafted Vinny Prospal in the third round of 1993. He only spent 59 games with the Flyers during his first run in Philly in 1997 and 1998. He returned late in the 2008 season where he’d play 18 regular season games and 17 playoff games.
7/8/95 – 1996 fifth round pick (Per-Ragnar Bergqvist) for Rob Zettler
Zettler was a defenseman, who played infrequently with the Flyers over the previous season. He would enjoy the best season of his NHL career with the Leafs in 1996-97 with two goals and 14 points. He played in the organization until he was left exposed during the 1998 expansion draft, ultimately being claimed by Nashville.
The Flyers drafted Swedish goaltender Per-Ragner Bergqvist with the fifth round pick in 1996, but he never made the jump to North America.
8/30/95 1996 first round pick (Dainius Zubrus), 1997 second round pick (Jean-Marc Pelletier), 1996 fourth round pick (Mikeal Simons) (traded to LA) for Dimitri Yushkevich, 1996 second round pick (Francis Larivee)
Dmitri Yushkevich was an unpolished but talented defenseman for the Flyers. The Leafs took him on as a project in this trade and he developed into one of the better shut down defensemen of his era.
The Flyers drafted Dainius Zubrus 15th overall in 1996. He’d play three underwhelming seasons in Philadelphia before he was later traded to the Canadiens. all in all, he’s play juts shy of 1,300 NHL games in his career which spanned 20 seasons. They also took goalie Jean-Marc Pelletier, who played one game with the Flyers in 1999.
The Flyers later traded the 1996 fourth round pick to the Kings in exchange for veteran forward John Druce and a 1997 seventh round pick that landed them Todd Fedoruk.
The Leafs drafted goalie Francis Larivee in the second round of the 1996 NHL draft but he would never play in the NHL.
9/26/00 – Chris McAllister for Regan Kelly
Chris McAllister was a hulking defenseman, clocking in at 6’8 and 250lbs. He’d patrol the Flyers’ blueline for two-and-half years, racking up 258 penalty minutes, before getting traded to Colorado.
Regan Kelly was the Flyers’ eighth round pick in 2000 but never made it to the NHL. He did play three seasons with the Leafs’ AHL affiliate before heading to Europe for a brief period before retiring.
2/14/11 – Kris Versteeg for 2011 first round pick (Stuart Percy), 2011 third round pick (Josh Leivo)
In one of the forgotten worst trades in Flyers’ history, they acquired forward Kris Versteeg ahead of the 2011 trade deadline in exchange for first and third round draft picks. Versteeg played 27 regular season games and 11 playoff games and combined for 17 points. He was traded during the summer of 2011 to the Florida Panthers for the draft pick that ultimately became Shayne Gostisbehere.
Luckily for the Flyers, the high price they paid to acquire his services didn’t manifest quite as well for the Leafs, who drafted defenseman Stuart Percy 25th overall in 2011, who only played 12 NHL games, and Josh Leivo, who was a fringe-NHLer who played 84 games for the Leafs in six seasons.
6/23/12 – Luke Schenn for James Van Riemsdyk
Van Riemsdyk was the second overall pick in 2007 and Luke Schenn was the fifth overall pick in 2008. In the never ending battle of the Flyers searching for a top defenseman, they sent JVR to Toronto for Luke Schenn. Both players weren’t exactly living up to their draft hype. The swap was made and Schenn continued to be relatively mediocre in Philly for three and a half seasons before he was traded to the Kings.
JVR had the most successful seasons of his career in Toronto, posting 154 goals and 294 points in 413 games, including a career best 36-goal season in 2017-18 and 62 points in 2016-17. He signed as a free agent with the Flyers during the 2018 offseason.
6/26/15 – 2015 first round pick (Travis Konecny) for 2015 first round pick (Gabriel Carlsson), 2015 second round pick (Jeremy Bracco)
The Flyers traded up five spots to draft Travis Konecny 24th overall. The Flyers originally acquired the pick in the Braydon Coburn trade. They threw in the 61st overall pick, originally acquired from Chicago in the Kimmo Timonen trade, to make the deal happen.
The Leafs traded their newly acquired 2015 first rounder to the Columbus Blue Jackets for a second round pick and a third round pick. They drafted defenseman Travis Dermott in the second round and forward Martin Dzierkals in the third round.
The Leafs drafted forward Jeremy Bracco, who spent three seasons in the AHL before heading to Europe to continue his career.
By: Dan Esche (@DanTheFlyeraFan)