Which current athletes have the longest tenures in Pittsburgh?

The reality of modern-day sports is that players rarely spend their careers in just one town.

Free agency, trades, owners unwilling to open their wallets (**cough cough Pirates cough cough**), salary caps, declining skills and a host of other reasons mean players can bounce from city to city over the course of their careers.

But some athletes do become entrenched in cities, and Pittsburgh is home to quite a few. The Penguins, for example, have Sidney Crosby, Evgeni Malkin and Kris Letang, who started their NHL-record 19th season together on Oct. 9, 2024.

Here’s a look at the current longest-tenured athletes in Pittsburgh, as of Aug. 5, 2025:

Sidney Crosby: Oct. 5, 2005

Sidney Crosby may have been nicknamed “Sid the Kid” at the start of his career, but he’s grown quite a bit in his 17 years in Pittsburgh. In that time, the Penguins center has won three Stanley Cups, the Hart Memorial Trophy (twice), the Art Ross Trophy (twice) and the Conn Smythe Trophy (twice), among other awards.

Crosby played his first game on Oct. 5, 2005, against the New Jersey Devils, finishing with an assist and three shots in a 5-1 loss.

Kris Letang: Oct. 5, 2006

Defenseman Kris Letang has been a steady presence on the Penguins’ blue line, winning three Stanley Cups, earning eight top-10 finishes in Norris Trophy voting and being named to six All-Star games.

Letang’s first game came in a 4-0 win over the Philadelphia Flyers on Oct. 5, 2006, when he finished plus-one in 15:01 of ice time.

Evgeni Malkin: Oct. 18, 2006

Center Evgeni Malkin has provided, with Crosby, one of the most potent one-two punches in recent NHL history. Malkin has won three Stanley Cups, the Calder Memorial Trophy, the Art Ross Trophy (twice), the Hart Memorial Trophy and the Conn Smythe Trophy.

Malkin’s NHL debut came on Oct. 18, 2006, when he scored the Penguins’ only goal in a 2-1 loss to the New Jersey Devils.

Cameron Heyward: Sept. 11, 2011

Defensive tackle Cameron Heyward has been a dominant force for the Pittsburgh Steelers’ defense since becoming a starter in the 2013 season. He’s recorded 78.5 career sacks (through the 2022 season) and been a team captain for eight straight seasons.

Heyward made his NFL debut on Sept. 11, 2011, recording one tackle in a 35-7 loss to the Baltimore Ravens.

Bryan Rust: Dec. 13, 2014

Right wing Bryan Rust has hit double-digits in goals for seven straight seasons with the Penguins, helping them to win Stanley Cups in 2016 and 2017.

Rust’s NHL debut came on Dec. 13, 2014, where he racked up one hit and four penalty minutes in 6:02 in a 4-3 shootout loss to the Columbus Blue Jackets.

Chris Boswell: Oct. 12, 2015

Place-kicker Chris Boswell has been consistent for the Steelers in his eight seasons with the teams, ranking 11th all-time in the NFL in field goal percentage at 86.3%.

Boswell joined the team midseason in 2015, making his debut on Oct. 12, 2015. He kicked a 47-yard field goal and three extra points in a 24-20 win over the San Diego Chargers.

Tristan Jarry: April 9, 2017

Penguins goaltender Tristan Jarry debuted at the end of the 2016-17 season but didn’t become a regular until the 2019-20 season. Twice in the past three seasons, Jarry has finished in the top 10 in Vezina Trophy voting.

Jarry made his NHL debut on April 9, 2017, in the team’s final game of the regular season. He made 22 saves on 25 shots in a 3-2 loss to the New York Rangers.

T.J. Watt: Sept. 10, 2017

Linebacker T.J. Watt has been a dominant force for the Steelers, including being named the Defensive Player of the Year in 2021.

The Steelers’ first-round pick earlier in 2017, Watt made an immediate impact with two sacks and an interception in his first game, as Pittsburgh beat the Cleveland Browns, 21-18.

Bryan Reynolds: April 20, 2019

Bryan Reynolds has blossomed into an All-Star outfielder for the Pirates after finishing fourth in National League Rookie of the Year voting.

Originally drafted by the San Francisco Giants, Reynolds arrived in the trade that sent Andrew McCutchen out west. Reynolds singled in his debut, a 3-1 win over, fittingly, the Giants.

Mitch Keller: May 27, 2019

Mitch Keller blossomed into one of the Pirates’ top pitchers, taking the mound as the opening day starter in 2023 and 2024. He signed a five-year, $77 million contract extension in February 2024.

Selected in the second round of the 2014 draft, Keller took the loss in his debut, allowing seven hits and six unearned runs while striking out seven in four innings in an 8-1 loss at Cincinnati.

Next up

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Rickard Rakell, Penguins, March 22, 2022

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