Will these 9 long-tenured free agents stay or go?

Will they stay or will they go?

That’s often the question surrounding top free agents. These players have to choose between remaining with their team -- perhaps even the team that drafted or signed them, developed them and brought them to the Majors -- and taking advantage of the open market to see if the grass is greener somewhere else.

Juan Soto ultimately picked the Mets over the Yankees, but he was only in the Bronx for a single season before heading to Queens. Some other free agents faced longer-term attachments, though. Kyle Hendricks (11 seasons with the Cubs) and Max Fried (eight seasons with the Braves) had pitched for only one Major League team apiece before departing, Hendricks to the Angels and Fried to the Yankees. Shane Bieber, on the other hand, opted to remain in Cleveland for an eighth season with the Guardians, who drafted him back in 2016.

More of these decisions loom as the Hot Stove kicks into high gear after the Winter Meetings. Below is a look at nine notable free agents, each of whom spent at least the past six seasons with the same team before entering the market. Who will don a new uniform next year, and who will feel the pull of home? (Players are listed in order of tenure with their 2024 team.)

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Clayton Kershaw, LHP, Dodgers
17 seasons w/ LAD | Debut: May 25, 2008

In recent offseasons, there was some suspense about whether Kershaw would continue to pitch, and if so, do it for the Dodgers. (His hometown Rangers have loomed as a potential late-career destination.) Not so this time around. Despite (or perhaps because of) Kershaw’s frustrating 2024 season -- he made only seven starts between injuries -- he stated his intention to pitch in 2025 even before the Dodgers clinched Kershaw his second World Series ring. As Los Angeles celebrated that achievement, Kershaw followed up by saying he would be a “Dodger for life.” Because of that, Kershaw declining his player option for next season was seen as purely a procedural move, and he still figures to be back in Dodger Blue, looking to overcome offseason surgeries on his left toe and left knee to lock up his 3,000th strikeout.

Chance to return: 10/10

Max Kepler, RF, Twins
10 seasons w/ MIN | Debut: Sept. 27, 2015

Kepler was just 16 years old when the Twins signed him out of Germany in 2009. By the time next season begins, he’ll be 32. That’s essentially half a lifetime with one organization. If Kepler leaves the Twins, he’ll do so having played the 16th-most games for the franchise (1,072) since it moved from Washington, D.C., to the Twin Cities in 1961. He is also Target Field’s all-time home run leader and has started every Opening Day for the team in right field since 2017. Unfortunately for Kepler, injuries marred his 2024, so he entered free agency coming off the least productive season of his career. Given the Twins’ needs and professed budget constraints, a return seems unlikely, but if that’s the case, he sounded at peace with it back in September.

Chance to return: 2/10

Alex Bregman, 3B, Astros
9 seasons w/ HOU | Debut: July 25, 2016

The Bregman Era in Houston has been prosperous. In 2017, when he played his first full MLB season, the Astros embarked upon a still-active streak of eighth straight playoff appearances, including seven trips to the ALCS, four trips to the World Series and two championships. Bregman has been a key contributor throughout that incredible run, and while it hasn’t all been smooth sailing (due mainly to the Astros’ sign-stealing scandal), his tenure with the franchise will go down as a rousing success no matter what happens this offseason. The Astros had expressed optimism about retaining Bregman, but that was before the club dealt star right fielder Kyle Tucker to the Cubs on Friday, in a move that netted them third baseman Isaac Paredes. It's not clear if that means the end of Bregman's time in Houston, since the club theoretically could use Paredes to fill another hole at first base. Still, the writing seems to be on the wall here.

Chance to return: 3/10

Anthony Santander, RF, Orioles
8 seasons w/ BAL | Debut: Aug. 18, 2017

The Rule 5 Draft was conducted earlier this week at the Winter Meetings, and each team that selected a player could only hope to hit it as big as the Orioles did with Santander eight years ago. At the time, Santander had spent five seasons in the Cleveland system without reaching Double-A. Baltimore managed to keep him in the organization despite minimal playing time in 2017, and Santander eventually became a key lineup piece for an Orioles team that climbed out of its deep rebuild to make back-to-back playoff appearances in 2023-24. A career-high 44 homers this past season set the switch-hitter up for a big payday, but that doesn’t figure to happen in Baltimore, considering the team’s glut of young position player talent.

Chance to return: 1/10

Christian Walker, 1B, D-backs
8 seasons | AZ debut: Sept. 10, 2017

Walker is the only player on this list who has not spent his entire Major League career with one team. With that said, he logged only 13 games for the Orioles from 2014-15, then bounced around the waiver wire in the 2016-17 offseason before landing in Arizona. Once the D-backs traded Paul Goldschmidt after the 2018 season, Walker got his long-awaited big league opportunity, at age 28, and ran with it. A three-time Gold Glove Award winner with multiple 30-plus homer seasons, Walker figures to do quite well in free agency despite the fact that he’ll turn 34 one day after Opening Day. There’s still a fit with Arizona if his market doesn’t develop as expected, but the D-backs also could go with Pavin Smith at first base while addressing other needs.

Chance to return: 3/10

Walker Buehler, RHP, Dodgers
7 seasons | LAD debut: Sept. 7, 2017

We’re only counting seasons played here, so Buehler doesn’t get credit for 2023, which he spent on the Dodgers’ injured list while rehabbing from Tommy John surgery. Before that setback, Buehler had established himself as one of the best starting pitchers in baseball, culminating with a 2021 season that saw him go 16-4 with a 2.47 ERA and fourth-place NL Cy Young Award finish. While Buehler’s return to action in 2024 was much rougher than anticipated (5.38 ERA over 16 starts), his postseason performance gave his market a last-minute boost. Buehler remaining in L.A. made a lot of sense, but the Dodgers opted not to extend him a qualifying offer, then signed Blake Snell and are considered a contender to land Roki Sasaki as well. With the starting pitching market as robust as it is, Buehler could wind up finding his best deal somewhere else -- though the Dodgers know as well as anyone that you can never have too many rotation options.

Chance to return: 5/10

Gleyber Torres, 2B, Yankees
7 seasons w/ NYY | Debut: April 22, 2018

Big things were expected from Torres, a top-five prospect, when the Yankees acquired him from the Cubs in the Aroldis Chapman trade at the 2016 Deadline. Torres quickly became a two-time All-Star for New York -- at ages 21 and 22 -- and appeared on his way to superstardom when he bashed 38 home runs in 2019. But visions of Torres becoming a legend in pinstripes slowly withered over the next five seasons, even as he continued to produce above-average offense. Now that Torres is a free agent, the Yankees seem prepared to move on, especially since doing so would allow them to shift Jazz Chisholm Jr. from third base back to second.

Chance to return: 1/10

Pete Alonso, 1B, Mets
6 seasons | NYM debut: March 28, 2019

The Polar Bear quickly became a fan favorite in Queens when he burst onto the scene with 53 home runs and an NL Rookie of the Year Award in 2019. The four-time All-Star and 2024 postseason hero already has hit 226 homers in a Mets uniform, and just one more healthy season with the team would almost certainly push him past Darryl Strawberry (252) for the franchise record. Will that happen? The Mets had other priorities, but now that they have acquired Soto -- as well as some rotation help -- they seem to have no intentions of slowing down. And Alonso could be next. There is certainly an argument that he is worth more to the Mets than anyone else, given their history, and clearly, cost is not a prohibitive issue here. Plus, other serious suitors have been slow to materialize.

Chance to return: 7/10

Patrick Sandoval, LHP, Angels
6 seasons | LAA debut: Aug. 5, 2019

If Sandoval joins another team, he might not actually throw a Major League pitch for them until 2026. The left-hander underwent Tommy John surgery in late June, meaning that he figures to return to big league action near the end of next season, at best. It was that injury situation that led the Angels to somewhat surprisingly non-tender Sandoval last month, cutting him loose instead of paying him through arbitration for two more seasons. Given that move, it seems unlikely the Halos would bring back Sandoval, who nonetheless will be an intriguing option for teams making a long-term play for 2026 and perhaps beyond. Between 2022-23, Sandoval gave the Angels 55 starts and nearly 300 innings, with a 3.50 ERA (121 ERA+).

Chance to return: 1/10