Free agents the Yankees failed to re-sign

When the Yankees want to bring a player back, they do not often let one of their own leave in free agency. Call it the powerful pull of the pinstripes — and of course, being a big-market, big-budget team doesn’t hurt, either.

Just how powerful that pull is, though, will be put to the test this offseason. Juan Soto, the biggest free agent on the market, will have no shortage of suitors given his age (26) and historic career production (especially alongside Aaron Judge in 2024) to this point. Will the superstar slugger stick around?

“I’m really happy with the city, with the team, how these guys do,” Soto said after the Yankees lost the World Series to the Dodgers. “But at the end of the day, we’re going to look at every situation, every offer that we get, and then take a decision from that.”

In some ways, Soto is different from the names below, because he’s not a homegrown Yankee and he came aboard with only one year of club control — after being acquired in a blockbuster trade with the Padres in December 2023 — before reaching free agency. Thus, he doesn’t have the same longstanding link to the Bronx that many other players who ultimately re-signed did.

Soto’s free agency is going to be fascinating to watch, and whether he returns will have a massive impact on the Yankees’ offseason and future.

When it comes to free agents of the past, the Yanks certainly have had some close calls. Going back to the Wild Card Era, which coincided with the franchise’s return to dominance as a dynasty, arguably the four biggest are:

• Alex Rodriguez: At the instruction of agent Scott Boras, the superstar third baseman infamously opted out of the remainder of his then-record contract in the middle of Game 4 of the 2007 World Series.

• Derek Jeter: The longtime shortstop and fan favorite, “The Captain” endured a somewhat tumultuous negotiation with the Yanks during the 2010-11 offseason.

• Aaron Judge: After turning down a large extension offer prior to Opening Day, Judge authored a mind-blowing, MVP-winning season in 2022. He was seriously pursued in free agency by the Giants and Padres, with some forecasting a return to his native California.

Ultimately, all four of them eventually re-signed with New York.

There have been instances, however, when the Yankees were unable to keep someone they coveted once he hit the open market. The list below is proof that once a player is free to sign anywhere, anything can happen.

Here’s a rundown, in reverse chronological order, of some of the bigger names the Bronx Bombers tried but failed to hang onto — and just how shocking the departure was.

Canó entered free agency coming off four straight All-Star appearances, four consecutive Silver Slugger Awards and four top-10 AL Most Valuable Player Award finishes from 2010-13, so the expectation was the Yankees would want to secure the superb second baseman for good. Wary of the fact that he was already on the wrong side of 30, however, the club’s front office executives aimed to make it happen on their terms at $175 million over seven years.

The Mariners blew that figure out of the water, presenting Canó with an offer he couldn’t refuse at 10 years and $240 million — at the time tied for the fourth-largest contract in MLB history with Albert Pujols, behind only Joey Votto’s extension with the Reds and the two deals signed by Rodriguez.

This one came with a twist. When Clemens stepped off the mound after a strong performance in Game 4 of the 2003 World Series — a wild Marlins win on Alex Gonzalez’s walk-off homer in the 12th inning — it looked like it very well might be his final outing ever. After all, the then-41-year-old right-hander had planned to retire at season’s end, which he did when the Yankees lost that Fall Classic.

Thing is, Clemens changed his mind a couple of months later, motivated in part by longtime rotation mate Andy Pettitte’s decision (see below) to depart the Yankees and head to Houston, where both pitchers had played high school ball. The about-face was a genuine surprise to the Yankees, who likely would have tried to retain Clemens even at his advanced age. “He told the world he was retiring,” owner George Steinbrenner said in a statement, “and we had no choice but to believe him.”

A member of the Yankees beloved and celebrated “Core Four” — along with Jeter, closer Mariano Rivera and catcher Jorge Posada — Pettitte was a stalwart in the club’s rotation from 1995-2003, averaging 31 starts and 199 innings per year and winning four rings in that span. Given that foundation, it seemed highly possible Pettitte would pitch in pinstripes his whole career.

“I just didn’t think there was any way I wasn’t going to end up back [with New York],” Pettitte said after negotiations stalled with the Yanks at the outset of the offseason.

The Astros swooped in and persuaded Pettitte to return to his roots — the left-hander was born in nearby Deer Park, Texas — despite an offer ($31.5 million over three years) that was less than the one the Yankees extended ($39 million over three years, but with only the first two seasons guaranteed).

“I thought the pull of home is really what we were up against,” Yankees general manager Brian Cashman said of Pettitte’s shocking departure, “and that’s ultimately what happened.” This loss was compounded shortly thereafter when Clemens came out of retirement (for the first time) to join Pettitte and the Astros, with whom both pitched from 2004-06, including a run to the World Series in ’05. They also then both returned to the Yankees in 2007, with Pettitte sticking around long enough to help them win it all again in ’09 before retiring after ’13.

Acquired by the Yankees from the Mariners, along with first baseman Tino Martinez and fellow reliever Jim Mecir, in what proved to be a dynasty solidifying deal in December 1995, Nelson was a key weapon in the reliable New York bullpens of the late ’90s. He recorded a 3.41 ERA and a 9.6 K/9 while averaging 61 appearances in his five seasons in the Bronx and capturing four championships in that time.

The Yanks tried to retain Nelson once he hit the open market after the 2000 campaign, offering him $9 million for three years. Their bid, though, was topped by the Mariners, who landed Nelson at $10.65 million. The 6-foot-8 righty went on to earn the only All-Star nod of his 15-year career in his first season in Seattle, as part of the 2001 team that won an MLB-record 116 games.

The Yankees of the early aughts never quite managed to replace Nelson’s late-inning nerve as a bridge to Rivera, and in fact, they wound up reacquiring him in a trade from the Mariners — yes, again — in August 2003.

When Wetteland chose not to exercise his option for a 1997 encore, the Yankees did not pursue him hard, but it still was slightly surprising when the closer left following two impressive years with New York. After all, the hard-throwing righty — who ended up signing a four-year, $23 million contract with the Rangers — had just won MVP of the 1996 World Series by closing out all four wins of the Yankees’ first championship since ’78.

“You knew the day after the season was over that we wouldn’t have all of the people back,” then-manager Joe Torre said of the club’s roster turnover that offseason, which also included the next name on this list. “We were happy to accomplish what we did with the people we had. Now, you just turn the page.”

For the Yankees, that meant turning the ninth inning over to Rivera. Although there were questions about whether the breakout setup reliever could handle the increased pressure of the closer’s job considering he only had five career saves to his name at that point, Rivera proved more than capable — and made the Yankees’ decision-makers look like geniuses.

Jimmy Key, LHP
Signed with: Orioles in December 1996

After Key helped the Blue Jays win their first of two straight titles in the 1992 season, the Yankees targeted him as a free agent to address a glaring need in the rotation. He succeeded right away, earning an All-Star berth in both ’93 and ’94, as well as a second-place finish in the AL Cy Young Award voting in the latter year.

The crafty lefty also pitched well in the ’96 postseason as New York won its first of four World Series in five years, but his performance had slipped during the regular season, and the Yankees had their doubts about Key holding up as he entered his age-36 season. They decided not to chase after him too much, leaving Key to ink with the O’s. The Yanks instead made what some felt was a controversial choice by pivoting to another veteran southpaw — David Wells, who had been with Baltimore.

Key pitched well for the O’s in ’97, earning his fifth career All-Star appearance, but he was out of baseball a year later. Wells, meanwhile, became a reliable starter right away for the Yankees, including a career campaign in New York’s historic ’98 season, which featured Wells’ memorable perfect game.

The Yankees’ signing of Goose Gossage in November 1977 was intriguing because lefty closer Sparky Lyle was coming off a Cy Young Award-winning season. The duo then combined to form a stellar back of the bullpen in ’78, with the younger, harder-throwing Gossage taking over the ninth inning and outpitching Lyle in the postseason as New York won its second straight title. That November, the Yanks sent Lyle to the Rangers in a swap that netted Dave Righetti, among others, paving the way for Gossage to emerge as one of baseball’s best late-inning arms over the next handful of seasons.

Gossage was dominant yet again in his walk year of ’83, making the then-32-year-old a coveted free agent. The Yankees wanted him back, but he said he would not re-sign in part because he didn’t want to play for the demanding Steinbrenner, so he inked a five-year, $5.5 million deal — among the biggest for a pitcher to that point — with the Padres. “He’s a fine pitcher,” said Murray Cook, the Yankees’ GM at the time. “We hated to lose him, and we made a sincere effort to keep him.”

Interestingly enough, while Gossage helped lead a young Padres team to its first Fall Classic appearance in ’84, the prickly veteran wound up having issues with San Diego’s front office and ownership, too. Gossage did end up returning briefly to the Yankees on a waiver claim in the summer of ’89 before retiring following ’94. He would be elected to the Hall of Fame in 2008.

Jackson already was an established superstar — he won three straight championships with the A’s from 1972-74 and captured the ’73 AL MVP — when he signed a historic five-year, $3 million contract with the Yankees as one of MLB’s first free agents in November 1976. It was under the New York limelight that he would go on to cement his status as an icon, particularly in the postseason.

Fueled by his World Series MVP performance in 1977, when he smashed three homers — on consecutive pitches, against three different hurlers — in the clinching Game 6, Jackson won consecutive rings with the Yankees in ’77 and ’78. “Mr. October” was born, and it seemed Jackson would stay in pinstripes forever.

He remained a stalwart in the Yankees’ lineup through the decade, including a second-place finish in the 1980 AL MVP voting. But by the following season, a 35-year-old Jackson was battling a calf injury and serving as the designated hitter more frequently. Although he was his usual productive self that October, the Yankees fell short in the 1981 Fall Classic, as Jackson hit the open market again.

Having signed another star outfielder in Dave Winfield in December 1980, New York and Steinbrenner did not pursue Jackson as feverishly this time around, and he landed a four-year contract with the Angels for around $1 million per season. “No matter what George would have offered, Reggie wouldn’t have played the outfield in New York,” agent Gary Walker said of his client’s decision to head to California, where Jackson lived. “There is enough of the little boy left in Reggie that he wants to play the outfield regularly,” said Walker.

In a statement after ending negotiations, Steinbrenner wished Jackson “the best of luck, except when he plays the Yankees,” adding that Jackson “truly is a great player and a certain candidate for the Hall of Fame when that time comes for him.” Indeed, it did, as Jackson was elected on his first ballot in ’93 — with the Yankees interlocking “NY” logo on his plaque.