He was that young, handsome, outspoken, funny, flashy, confident, and very talented player always willing and usually able to back up his words with his actions. Beloved by teammates and detested by opponents, he lived as hard as he played, and became almost as recognized and revered away from the game as when he was competing.

Derek Sanderson wasn't the first athlete to fit those descriptions, but he was unique in one respect: He became both a two-time Stanley Cup champion [...]

He was that young, handsome, outspoken, funny, flashy, confident, and very talented player always willing and usually able to back up his words with his actions. Beloved by teammates and detested by opponents, he lived as hard as he played, and became almost as recognized and revered away from the game as when he was competing.

Derek Sanderson wasn't the first athlete to fit those descriptions, but he was unique in one respect: He became both a two-time Stanley Cup champion with the Bruins, as well as something of a pop culture icon, despite taking what amounted to a back seat to other players when a case could be made that the situation should have been reversed.

“I was a left wing on the power in my rookie year,” Sanderson said on Tuesday, as he recalled the Bruins' 1970 Cup season during a video conference. “The next year Harry (Sinden, then the coach, later general manager and president) said ‘I don't think you're going to be happy about this, but I've thought about it all summer: I want you to take penalty-killing to an art form.'

I said ‘But what about the money? I won't get the points.' And he said ‘But we'll know. Your teammates will know, and I'll know.'”

Those who watched the “Big, Bad Bruins” from the late 1960s into the mid-1970s do remember Sanderson and Ed Westfall forming a penalty-killing duo that was as much a threat to score (Sanderson netted 18 shorthanded goals over the 1969-70 through ‘71-72 seasons, leading the NHL with seven in that last year) as to snuff an opposing power play. They'll also recall Sanderson being among the first NHL centers to focus on, and excel in, the art of winning faceoffs.

A bigger group has seen highlights of Sanderson making a single play: He's the one who threaded a pass through Blues defenseman Jean-Guy Talbot to Bobby Orr, who scored 40 seconds into overtime in Game 4 to end the Bruins' 29-year Stanley Cup drought on May 10, 1970.

The play, and Sinden's decision to start the Bruins' third/checking line (Sanderson, Westfall and left wing Wayne Carleton) over the line centered by 99-point scorer Phil Esposito, rank among Sanderson's favorite tales.

“(Sinden) came to me and said ‘Listen, usually these things end pretty quickly. The only chance they've got is if it ends quickly, so let's buy a couple of minutes,'” Sanderson recalled. “‘Get us past the opening … make it a defensive battle, and then eventually we're going to win.'”

“I sat beside (Esposito). He said ‘I can't believe that,' and I said, ‘Ah, well, what are you gonna do?' And once we got it in their zone, (the Blues) never got it out.”

Sanderson, the Calder Trophy winner as NHL Rookie of the Year in 1967-68 (24 goals, four on power plays, and 49 points in 71 games), didn't stop producing after Sinden made him a No. 3 center and full-time penalty-killer. He scored at least 24 goals in four of his first five seasons, topping out at a career-high 29 in 1970-71, and he scored 58 points a year later as the B's won their second Cup in three seasons.

In some ways, though, that obvious talent — combined with a nearly equal ability to generate headlines for off-ice pursuits such as talk show appearances and a friendship and nightclub co-ownership with New York Jets superstar Joe Namath — were Sanderson's downfall: The Philadelphia Blazers of the upstart World Hockey Association, seeking publicity and a drawing card as much as a player, overwhelmed Sanderson, then holding out for $80,000 from the Bruins, with a five-year, $2.6 million offer he couldn't turn down.

“It was not the right move for me,” said Sanderson, a millionaire at 26 who brought an increasing dependence on alcohol and painkillers and a growing list of physical ailments (primarily in his hips) to his new job. “My whole life, my whole world, all my friends were (in Boston). Then I went to Philadelphia, and … I don't know a soul.

“I take a cab to go see a movie, and I drove by a Rolls-Royce dealership. I wanted to see if the (Blazers') money was real, so I went in … and bought a Rolls Royce. That wasn't the smartest thing. I should have known I was in trouble, right then.”

The Blazers bought Sanderson out after just one season (and only eight games) and Sinden brought him back to Boston in 1973-74, but two injury-plagued seasons later, he was traded to the Rangers. He played for three more teams before running out of options after 1977-78; not long after that, Sanderson was broke and briefly homeless.

It was Orr who put Sanderson on a path to recovery that included years as an analyst on Bruins TV broadcasts and a career helping athletes with investments — which is perhaps why he recalls the ‘69-70 season, and his connection with Orr on the famous Cup-winning goal, with such fondness.

“Bobby Orr had a Cinderella year (league-leading 120 points, on 33 goals and 87 assists),” Sanderson said. “He did everything right — right onto another planet.

“For him to get that goal, that's what I was happiest about. Because he did everything for everybody.”