4 Fan-favorite players who should’ve retired with Red Sox

On Tuesday morning, Zdeno Chara announced that he’d signed a one-day contract with the Boston Bruins so that he could retire from the NHL with them.

Chara began his playing career with the New York Islanders and also played for the Ottawa Senators before joining the Bruins in 2006. After 14 seasons with the team, all as their captain, he departed for the Washington Capitals and a final season with the Islanders. But in his statement on Tuesday, Chara declared that he was “honored” to “officially finish [his] career with the team that has meant so much” to him and his family.

One-day contracts are a technicality, but the decision is a lovely gesture that shows a player’s affinity and bond with the franchise and fans. Of all the teams Chara played for, the Bruins are the ones he wants to be with before he hangs up his skates.

These deals occasionally happen in Major League Baseball, too. In 2010, Boston Red Sox star Nomar Garciaparra signed a one-day to retire with his former team. Shane Victorino, a key figure in Boston’s 2013 championship, returned to his beloved Phillies for the final day of his career. Hideki Matsui reunited with the Yankees for the ceremonial farewell in 2013.

With that in mind, here are four more players who should’ve retired with the Sox, if only for one day…

Babe Ruth

If someone ever builds a working time machine, it would be interesting to go back and tell Harry Frazee what’s going to happen to the Sox after he sells Babe Ruth’s contract to the New York Yankees. Maybe if he knew that the deal would ignite an 86-year championship drought full of heartache and suffering, he wouldn’t do it (though that opens up a whole can of worms about 2004 and David Ortiz, so let’s not think too hard on the specifics.)

But really, what the Sox should’ve done was bring Ruth back for the end of his career. Ruth desperately wanted to be the Yankees’ player-manager, but they passed him over for the position multiple times. The Sox did reportedly consider trying to hire him, but it never came to fruition.

In the early 1930s, Ruth’s relationship with the Yankees soured due to his continued campaigning to replace manager Joe McCarthy. y February 1935, the Yankees had agreed to trade him to the Boston Braves, who told Ruth they wanted to make him their manager.

Really, the Braves wanted to use Ruth as more of an attraction to draw a crowd. His assistant manager title was mostly vanity, and he barely played. By June 2nd, he’d officially retired.

Why didn’t the Sox try to bring him home? In 1935, they had a new owner richer than any other in the league and happy to spend money to turn the team around. It would’ve been less than two decades since their last championship, which can hardly be considered a drought by the 86-year standard they’d end up setting. Maybe by reuniting with Ruth, they could’ve avoided the curse altogether.

Carlton Fisk

The bungling of Carlton Fisk’s contract is one of Boston’s greatest mistakes.

At the end of the 1980 season, Fisk became a free agent by accident. Sox GM Haywood Sullivan had put his contract in the mail one day after the deadline, accidentally rendering their star catcher a free agent.

In March 1981, the New Hampshire native signed a five-year deal with the White Sox. He and the team achieved a lot during his tenure. They won their first division title in 1983, he hit for the cycle in 1984, and won all three of his Silver Sluggers with Chicago.

But in June 1993, right after Fisk broke Bob Boone’s record for all-time games caught, the White Sox abruptly released him from the team while they were on a road trip. And when they made the postseason that fall, he went to the clubhouse to wish his former teammates good luck and was thrown out.

The horrible treatment and insult Fisk endured at the end of his time with the White Sox played a part in the catcher choosing to wear a Red Sox cap on his bronze Hall of Fame plaque, instead. Both teams retired Fisk’s number, and he’s in the Red Sox Hall of Fame as well as Cooperstown. Fenway’s left-field foul pole is named the Fisk Foul Pole in honor of his iconic “If it stays fair!” home run in the 1975 World Series.

But he should’ve switched Sox again before hanging it up.

Jon Lester

Jon Lester remains one of the only great pitchers the Red Sox have ever developed, and his story is remarkable.

Less than two months after making his MLB debut in June 2006, Lester was diagnosed with lymphoma. He spent the offseason undergoing chemotherapy and his cancer went into remission that winter.

By July 2007, he was back with the big-league club. A few months later, in the first postseason start of his career, he pitched the Sox to victory in Game 4 of the World Series. He threw a no-hitter the following May.

Lester was crucial to the Sox’ 2013 championship run, their first postseason since 2009. He started Game 1 of the ALDS, ALCS, and World Series.

In the final season with the Sox, they traded him to the Oakland A’s at the deadline. That fall, he signed a six-year deal with the Chicago Cubs, and in 2016, he helped them win their first World Series in 108 years. When he became a free agent after the 2020 season, he signed a one-year deal with the Washington Nationals, who then traded him to the St. Louis Cardinals at the deadline. When the season ended, he announced his retirement.

Lester remains one of the current Sox ownership’s biggest mistakes. When Lester made it known that he was open to a team-friendly deal, the ownership got greedy. They famously lowballed him in the negotiations, and he rightfully declined their embarrassing four-year, $70M offer, as ‘team-friendly’ should not have meant ‘well below market value.’ The negotiations stalled from there, and they traded him at that summer’s deadline.

The Sox tried again when he became a free agent that winter, but by then, it was too late. Lester has maintained for years that he would have accepted six years in the $120M range, significantly less than what the Cubs ended up giving him. Instead, the Sox went out and gave David Price the biggest pitching contract in MLB history, and came away from the experience underwhelmed.

Even principal owner John Henry admitted years later that they’d made a huge mistake, saying “we blew the Jon Lester signing.”

And with all the overcorrections they made in the years following, they never found a way to correct that mistake.