Here are the best players who left Boston and went on to win championships elsewhere

When the Celtics decided earlier this month to trade Jaylen Brown to the 76ers after 10 seasons, nine playoff runs, and a championship, rather than face the possibility of another hefty contract extension, the decision cut two ways.

Read more Talking Points: Amazon enjoys a strong quarter; Taco Bell bounces back; Jersey Mike’s goes public

On one hand, a city that has piled up championships over the past two decades watched yet another face of one of those teams leave.

On the other hand, Brown, like several others before him, left Boston while still fully capable of carving out success wherever he landed.

From Tom Brady to Mookie Betts to Ray Allen to Bruce Cassidy, Boston has had to not only watch familiar faces leave, but see many of them lift trophies elsewhere.

Time will tell if Brown does the same, but here’s a look at players from each of the city’s four major franchises who have found success after departing the Hub.

The Celtics have never had to go through a loss like Brown.

Paul Westphal spent his first three seasons in Boston before becoming a four-time All-NBA selection with the Suns. Chauncey Billups played just 51 games as a rookie with the Celtics. It took eight seasons before he emerged as the elite point guard who led the Pistons to the 2004 NBA championship and won Finals MVP.

Al Jefferson spent his first three seasons in Boston before earning All-NBA Third Team honors and finishing eighth in MVP voting with Charlotte in 2013-14.

Among players who began their NBA careers with the Celtics, those are the only three who later earned All-NBA honors after leaving the franchise.

While Allen’s departure for Miami was bitter — he won another championship in his first season with the Heat in 2013 — he was already a future Hall of Famer by then and played just two seasons there before retiring.

The Red Sox are a different story. Whether it’s Babe Ruth and Cy Young, or Roger Clemens and Johnny Damon, or Manny Ramirez and Pedro Martinez, watching stars leave Boston and shine on another stage is part of the Sox’ DNA.

To this day, none of Boston’s four major franchises has watched stars not only walk out the door but thrive elsewhere more than the Red Sox.

The Sox traded Betts to the Dodgers in 2020. Betts has added three World Series titles to the one he won in Boston. He’s one of 10 Red Sox players who left Boston after 2015 and later won a World Series.

Read more Cerberus, former Steward Health Care private equity owner, settles with creditors

Over the next five years, the club slowly continued to dismantle the team that won the 2018 title — from Xander Bogaerts leaving in free agency, to Chris Sale agreeing to a trade to Atlanta, to Rafael Devers forcing a midseason trade to San Francisco.

Until last season, the Patriots spent virtually the entire decade overhauling.

The split between Brady and Bill Belichick was the most seismic in the Boston sports landscape. Brady left for Tampa Bay for the 2020 season, recruited tight end Rob Gronkowski to join him, and immediately won a Super Bowl.

As much of a knife twist as Brady’s immediate success was, it was also unusual. Few former Patriots continued playing at an elite level after leaving New England.

The player who’s arguably thrived the most since departing is Joe Thuney. He left the Patriots in 2021 after five seasons and two Super Bowls, then won two more championships with the Chiefs, became a three-time Pro Bowler and All-Pro, and signed a two-year, $35 million contract with the Bears last year.

Continuity has been the Bruins’ trademark. Patrice Bergeron, Zdeno Chara, David Krejci, Tuukka Rask, and Brad Marchand all spent extended runs in the Spoked-B jersey, giving Boston virtually all of their best years.

Coaching-wise, the most glaring departure was Bruce Cassidy, who won a Stanley Cup in Las Vegas in 2023 after being fired in Boston the year before.

As for players, the Bruins traded No. 5 overall pick Phil Kessel in 2009 after three seasons. He went on to score more than 400 goals, top 1,000 career points, and win three Stanley Cups. Tyler Seguin had superstar potential as the Bruins’ No. 2 overall pick in 2010, but his run in Boston lasted just three seasons. He was traded to Dallas, where he developed into one of the NHL’s top centers and has scored 311 career goals in 13 seasons.

The last former Bruin to win a Stanley Cup was Marchand, who was traded to Florida at the 2025 deadline after nearly 16 season in Boston. Marchand found his game in the playoffs, notching 10 goals and 10 assists in 23 games, helping the Panthers to their second consecutive Stanley Cup.

Also of note is Reilly Smith, who won the Bruins’ 7th Player Award in 2013-14 before eventually helping Vegas win the Stanley Cup with Cassidy in 2023.

The Celtics are in unfamiliar territory, with Brown still firmly in his prime and joining a division rival built to contend for championships. But Boston has been here before.

Read more On deck for the Red Sox: A series at Dodger Stadium, against the best of the best