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Five other times Boston Bruins legends retired while wearing the “wrong” jersey

There’s something admirable about watching a player spend most of, if not their entire, career with one team, but in reality, it’s rare that it even happens.

Life has a way of twisting and turning through the primordial ooze of existence before reaching some semblance of comfort and “happily ever after” doesn’t exist outside of fairytales.

Especially since the rise of players’ rights in free agency across the four major North American professional men’s sports leagues since the 1970s and salary caps over the years in the National Hockey League have an influence in determining fate.

Not everyone can be like Dit Clapper, Milt Schmidt or Terry O’Reilly and spend their entire NHL playing careers with the Boston Bruins, then have their numbers retired by the club.

Even Lionel Hitchman, Johnny Bucyk, Cam Neely and Rick Middleton played somewhere else before their Bruins days (Hitchman with the original Ottawa Senators from 1922-25, Bucyk with the Detroit Red Wings from 1955-57, Neely with the Vancouver Canucks from 1983-86 and Middleton with the New York Rangers from 1974-76).

There have been other players before that have either played most of their career with Boston, then departed or came and went after racking up Hockey Hall of Fame tenures in a Bruins uniform.

New Washington Capitals defender, Zdeno Chara, is just the latest in a list of players that spent the majority of their career in one city and came to be synonymous with that jersey before leaving town and finishing their NHL career elsewhere.

Despite being the captain of the Bruins for his entire 14-season stretch from 2006-20, there was a time when Chara wasn’t on Boston’s roster before.

It was in the years B.C.E. (Before Chara Era) when he was drafted by the New York Islanders in the 4th round (56th overall) of the 1996 NHL Draft, prior to making his league debut in the 1997-98 season, then spending four seasons on Long Island before being traded to the Ottawa Senators, where he spent another four seasons prior to joining the Bruins via free agency on July 1, 2006.

Chara may have been a fan favorite and commendable for his charity and volunteerism in the community, but there are no guarantees in life. There was always going to be an A.C.E. (After Chara Era).

Here are five other fan favorites that didn’t go out the way diehard Bruins fans necessarily wanted.

Tiny Thompson

Bruins fans loathed the trade that sent Thompson to the Red Wings on Nov. 28, 1938, to the point that they nearly revolted outside Boston Garden.

The franchise’s first star goaltender and member of the 1959 Hockey Hall of Fame class amassed a 252-153-63 record in 468 career games across 11 seasons with Boston from the 1928-29 season through part of the 1938-39 season.

His 74 shutouts remain a franchise record and are 39 more than his successor had, but B’s fans quickly warmed up to Frank Brimsek after Brimsek earned the nickname “Mr. Zero” by recording six shutouts in his first eight games in the 1938-39 season.

Oh, and, Thompson was the one that personally recommended then head coach and Bruins manager, Art Ross, sign Brimsek to replace him.

He just didn’t retire after the 1937-38 season like Ross thought he would, forcing Ross’ hand when he had two hot goaltenders— one established 35-year-old (Thompson) 1929 Stanley Cup champion, while the other an up-and-coming 23-year-old (Brimsek) that went on to win the Cup in 1939 and 1941.

Brimsek locked down Boston’s starting job in the crease until he was later traded to the Chicago Black Hawks in 1949, providing a sense of relief for Ross in one aspect of the team.

Thompson ended up playing parts of two seasons in Detroit and retired after the 1939-40 season at 36-years-old.

Had Thompson not been injured in practice five games into the 1938-39 season, there’s no telling what would’ve happened.

Eddie Shore

Shore wanted more than the league maximum salary of $7,500 ahead of the 1933-34 season and sat out the first month of the season while NHL president, Frank Calder, had to intervene to get him to agree to a deal with Boston as the defending Hart Memorial Trophy winner as the league MVP in 1932-33.

He spent parts of six seasons thereafter with the Bruins, but began what ultimately led to a falling out of sorts between Shore, Ross and the club.

After recovering from a debilitating injury late in his career, Shore had taken the time to purchase and play for the Springfield Indians of the American Hockey League (AHL) ahead of the 1939-40 season while maintaining a part-time role with Boston.

Ross was not thrilled with the idea of Shore— the franchise’s first superstar— spending any time away from the organization and— after the two couldn’t see eye-to-eye on many things— traded him to the New York Americans for Ed Wiseman and $5,000 on Jan. 25, 1940.

Shore appeared in 10 games for the Americans before retiring from the NHL thereafter.

Bobby Orr

Orr’s story is perhaps the most famous of those among Bruins legends to not have spent his entire career in Boston and retired elsewhere instead of while wearing the “Spoked-B”.

Long story short, Orr’s agent at the time, Alan Eagleson, neglected to mention to Orr that Boston’s offer for a contract extension prior to the 1976-77 season had a reduction in salary after Orr failed a physical, but included a minority stake in ownership of the club in the backend of the deal.

Though Eagleson is quoted as mentioning the terms of Boston’s contract offer in a Toronto newspaper, Orr was never directly told by his agent of the conditions the Bruins had and instead signed with the Black Hawks for $3 million flat to be paid over 30 years.

The player that was the reason many New England kids grew up playing hockey in the 1970s and scored the infamous 1970 Stanley Cup clinching goal in overtime against the St. Louis Blues left the Bruins not with a bang, but a whimper as he was limited to just 26 games in a Chicago uniform from the 1976-77 through 1978-79 seasons— forced to retire at age 30 due to knee injuries in a time when rehabilitation and knee replacement surgery wasn’t quite what it is now.

Eagleson later served time in prison for fraud and embezzlement and lays claim to being the only person to have resigned from being a distinguished member of the Hockey Hall of Fame in April 1998. 

Phil Esposito

Esposito’s career began in Chicago in the 1963-64 season before playing the next three full seasons with the Black Hawks until May 15, 1967, when then Bruins General Manager, Milt Schmidt, traded Pit Martin, Jack Norris and Gilles Marotte to Chicago in what became one of the most lopsided trades in the history of major North American professional sports.

In return for Martin, Norris and Marotte, Boston acquired Esposito, Ken Hodge and Fred Stanfield— three players that became key contributors to the Bruins’ two Stanley Cup championships in 1970 and 1972.

Esposito had a modest 174 points in 235 games with Chicago (.740 points per game) from 1963-67, and had over 1,000 points (1,012, to be exact) in 625 games with Boston (1.62 points per game) from 1967-75.

But on Nov. 7, 1975, with the Bruins needing to shake things up a bit and revamp their roster, Esposito and Carol Vadnais were packaged to the New York Rangers for Brad Park, Jean Ratelle and Joe Zanussi.

Once again, fans were ready to storm the Bastille (or the Boston Garden, if you will) when then GM Harry Sinden shipped Esposito out of town, but quickly came to appreciate Park’s service on the blue line as the transition from Bobby Orr to Ray Bourque.

Even an aging Ratelle found new life in Boston for a brief period of time.

Meanwhile, Esposito amassed 404 points in 422 games for the Rangers (.957 points per game) before hanging up the skates after the 1980-81 season at 38-years-old.

Ray Bourque

Bourque was Boston’s 1st round pick (8th overall) in the 1979 NHL Draft. The native of Montréal, Québec spent parts of 21 seasons in a Bruins uniform tallying 395-1,111—1,506 totals in 1,518 career games in black and gold from the 1979-80 season until the 1999-2000 season trade deadline on March 6, 2000.

The Bruins made two Stanley Cup Final appearances in Bourque’s tenure on the blue line in the Hub, but lost to the Edmonton Oilers in 1988 and 1990.

Nearing the end of his career, Sinden dealt Bourque to the Colorado Avalanche with Dave Andreychuk for Brian Rolston, Martin Grenier, Samuel Pahlsson and a 2000 1st round pick (previously acquired from New Jersey, Boston selected Martin Samuelsson) as a favor for Bourque to chase after his elusive Cup ring with a Stanley Cup favorite rather than with a floundering Boston team.

Andreychuk wouldn’t win a Cup until four years later with the Tampa Bay Lightning in 2004, as the Avalanche came up short in the 2000 Western Conference Final— losing in seven games to the Dallas Stars.

But Bourque stuck around for one more season and lifted the Cup at 40-years-old in his 22nd NHL season after Colorado defeated the New Jersey Devils in seven games in the 2001 Stanley Cup Final.

Though he had finally won a Cup, it was with the Avalanche and not the Bruins.

Bourque promptly retired from his playing days on June 26, 2001, and had his No. 77 retired in both Boston and Denver.

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