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Free agency is a practice both cruel and rewarding, something the New York Yankees know all too well.

Currently, the Bronx Bombers are licking their wounds after losing out on Japanese ace Yoshinobu Yamamoto. He spurned the Yankees to sign a 12-year contract with the Dodgers and join WBC teammate Shohei Ohtani. Quite the surprise since the Yankees were long considered the front-runners for Yamamoto.

But such is free agency. There are ups, downs, and lateral moves. The Yankees have experienced the high of signing Gerrit Cole, re-signing Aaron Judge, and losing Robinson Cano all in the last decade. Ask #YankeesTwitter, and it’s still unforgivable that Brian Cashman didn’t sign Bryce Harper and/or Manny Machado.

Granted, every team has reasons for pursuing or not pursuing a free agent. They could cost too much money, or perhaps their persona just doesn’t mesh with the clubhouse. Sometimes, a player just doesn’t want to go to a particular team, like how Ken Griffey Jr. famously didn’t want to play for the Yankees. More on that later.

Seeing as how fans deal only in absolutes and prefer to play Coulda/Woulda/Shoulda, we’ll indulge them this one time. Here’s a team of players the Yankees could have traded for or signed in free agency, but didn’t.

Catcher- Carlton Fisk. The Yankees-Red Sox blood feud was so intense in the 1970s that the idea of a player from one team leaving for the other was unthinkable. Fisk spent 11 years in Boston and threw the first punch in a brawl with New York’s Lou Piniella in 1976. He hit free agency in 1981, signed with the White Sox, and stayed until retiring in 1993.

However, the Yankees had a rough go at catcher after Thurman Munson’s tragic death in 1979. Rick Cerrone and Butch Wynegar tried, but were just the first two in a string of journeymen catchers up until Jorge Posada debuted. Imagine what could have been if George Steinbrenner offered a bigger five-year contract along with an apology for the brawls? The Yankees could have had yet another Hall of Fame backstop for five, maybe even ten years.

First base- Adrian Gonzalez. This one is admittedly very pie in the sky, as A-Gon’s prime happened when Mark Teixeira was firmly entrenched at first. Around the same time, the Padres sent Gonzalez to the Red Sox for Anthony Rizzo. Two years into a seven-year extension, Boston sent him to the Dodgers to offload salary.

But what if the Yankees got involved as a potential third team? Remember, the team’s DH situation was a bit of a revolving door in the 2010s. Imagine trading for Adrian Gonzalez and adding another lefty bat to the lineup? Not to mention the Yankees would then have two Gold Glove first basemen.

Second base- Julio Franco. Franco played for eight different teams in three different decades, winning a batting title along the way. In this case, we’ll rethink when Cleveland traded him to the Rangers in December 1988. The Yankees, having moved on from Willie Randolph, signed Steve Sax and his errant fielding in free agency.

Nothing against Sax, but the Yankees deserved more. Franco would have cost more, in both salary and trade pieces, but imagine that stance and swing with Yankee Stadium’s short porches. George Steinbrenner easily could have swung a trade if interested, and if the team’s farm system could be gutted further.

Shortstop- Manny Machado. Alright, we’ll cave. Maybe the Yankees should have sold high on Didi Gregorius after 2018 and been more aggressive in pursuing Machado. Brian Cashman’s analytics team would just have to shut up and deal with his bad fielding at shortstop.

In one world, the Yankees kept the streaky Gregorius for another year and made the mistake of sticking with Miguel Andujar. In another, perhaps both could have been traded for pitching and Machado would don the pinstripes.

Third base- Adrian Beltre. I like this idea so much that I even wrote a scenario in which it actually happened. A quick refresher: Aaron Boone never shreds his knee and the Yankees trade him to the Dodgers for Beltre at the deadline in 2004. In turn, Beltre re-signs with the Yankees and stays there for the rest of his career instead of five lost years in Seattle. The Mariners never sniffed the playoffs in that time.

This is indeed a controversial move, especially since it means the Yankees never trading for Alex Rodriguez. However, A-Rod was a walking soap opera while Beltre is about to become a Hall-of-Famer.

Left field- Nelson Cruz. Let’s rewind back to the 2013/14 offseason, when the Yankees signed Carlos Beltran almost instantly after losing Robinson Cano in free agency. The aging switch-hitter wasn’t terrible in pinstripes, but imagine if the Yankees gambled on Cruz instead. Remember, he ultimately signed a one-year deal in Baltimore following his ties to the Biogenesis scandal.

However, Cruz was younger and only just retired. He easily could have rotated between the outfield and DH in the Bronx, particularly with his strong throwing arm.

Center field- Ken Griffey Jr.- The Kid would have been a perfect Yankee, from his range in center to his perfect, beautiful swing. However, Griffey knew from the start that the Yankees were never in his future. As he detailed in his documentary “Junior,” he and his father Ken Sr. noticed some clear preferential treatment towards some players and their families. The younger Griffey never forgot and soon moved from Seattle to Cincinnati.

What if George Steinbrenner followed the Billy Martin playbook, called Ken Sr. to sincerely apologize, and speak hat in hand about how great his son would be as a Yankee? It still wouldn’t have worked, but what if it did? Moreover, what if Griffey wasn’t beset by constant leg injuries?

From the World Series prospects to maybe breaking the all-time home run record at Yankee Stadium, this will remain one of the biggest “What ifs” not just in New York, but across baseball.

Right field- Bryce Harper. I’ve said it before and I’ll say it again. Had the Yankees gone all in on Bryce Harper’s free agency, they almost certainly wouldn’t have signed Gerrit Cole, nor extended Aaron Judge. The long-term costs very likely outweighed the short-term benefits from signing him.

Except Bryce Harper is a generational talent and excellent leader. He’s turned the Philadelphia Phillies from baseball’s favorite punchline into a Pennsylvanian powerhouse. No matter how much signing him might have upended the Yankees’ budgetary plans, he’s strong enough in the clubhouse that the team would still contend.

Starting pitcher- Greg Maddux. This is a different entry from the rest because, unlike the others, this one almost actually happened. Maddux went on David Cone’s “Toeing the Slab” podcast and said as such. He was set to sign with the Yankees, but never got a formal contract offer because someone in their front office supposedly had a heart attack. The future Hall of Famer signed with Atlanta, and the rest is history.

It worked out fine for both teams, particularly since Maddux’s Braves only won a single World Series in the ’90s while the Yankees won three, including two against Atlanta. However, Maddux won three of his four consecutive Cy Young Awards with Atlanta and posted a 2.63 ERA in 11 years with the Braves. Imagine that same production, but with Maddux playing alongside the Yankees’ Core Four.

Bullpen- Lee Smith. We’re cheating a little bit here, as Smith played eight games for the Yankees in 1993 and posted a 0.00 ERA with three saves. The Yankees acquired him in a waiver deal with the Cardinals and he then signed with Baltimore in free agency. New York used Steve Howe at closer the following year before moving onto John Wetteland.

Except Smith, at the time, was MLB’s all-time saves leader and even notched his 400th career save with New York. He pitched four more years, including two as a closer. 1994 was his age-36 season and he still led MLB with 33 saves. The Yankees would have loved to have his consistency and experience until Mariano Rivera was ready.

Josh Benjamin has been a staff writer at ESNY since 2018. He has had opinions about everything, especially the Yankees and Knicks. He co-hosts the “Bleacher Creatures” podcast and is always looking for new pieces of sports history to uncover, usually with a Yankee Tavern chicken parm sub in hand.