Dear diary, it is time to get back to the old way. Red Sox, when Boston Red Sox president Larry Lucchino used the Star Wars–inspired insult after the Yankees outbid Boston to sign Cuban pitcher José Contreras. Now, the team is neither feared nor respected. Teams celebrate accomplishments at Yankee Stadium, like the Tampa Bay Rays just did.
Diary, it is time to put the fear back into oppponents and to, infuriate them, and make them respect the team. It starts with forgetting the self-imposed $300 million salary threshold. If the team wants success on the field and to reach its stated goal of winning the World Series, then it needs to spend money and acquire talent. Do you think the Yankees will do this?
Diary of a Yankees Fan #6: Free Agents

The Yankees need to acquire talent for the 2027 baseball season, if there is one. Fortunately, diary, there are free agents and trades out there that fill all of their needs. The team needs a right-handed hitting third baseman and catcher. They need a second baseman, a slugger, a closer, and additional relief pitchers. Here is a list of those free agent or trade targets.
Bryce Harper
The Yankees have reportedly targeted this player before. This is not a free agent target; it is a trade target. Harper offers versatility and is the kind of big name that, if the Yankees acquired him via trade, would make big waves. Harper’s versatility makes him an option for the outfield, first base, or DH in 2027. The Yankees have talented players at first base and designated hitter, but outfield could be an option. Plus, as we saw this past season, injuries can happen.
RHP Raisel Iglesias
The Yankees need to sign a closer. Incumbent David Bednar might cost too much for them to re-sign, even though he pitched well. Another, more affordable option is Raisul Iglesais, formerly of the Braves. He is 37 years old and might demand only a one-year deal, as opposed to the three- or four-year deal the 32-year-old Bednar would command.
LHP Adrián Morejón and RHP Mason Miller
The Yankees, diary, should add as many big-name relief pitchers as they can. Left-handed pitcher Adrian Morejon could be an alternative. He relies on a heavy sinker and has put up great numbers for the last three seasons. Last year he struck out more than one hundred batters. While they are raiding the Padres bullpen, they should consider trading for fireballer Mason Miller. The Yankees almost pulled the trigger on this deal in July, and the Padres were interested in Will Warren.
C Ryan Jeffers or Wilson Contreras
The Yankees could fill the gaps they have by signing free agent Ryan Jeffers. Remember when the Yankees almost traded for him in July? Now, all it would take to land the right-handed hitter is money. He is a decent defender and a good hitter. Another alternative would be the heavy-hitting Brewer, Wilson Contreras. The Brewers have shown they are willing to trade away stars in the last year of their contracts. That is the case for Contaras in 2027, and he could be had for a surplus Yankee starting pitcher, like Will Warren.
2B Luis Arraz
Arraz is a singles machine, who would get on base for the other sluggers in the batting order. He would also be a handy replacement for Jazz Chisholm Jr. Arraz got injured near the end of the 2026 season. His injury doomed the Phillies, for whom he had been a spark plug. An alternative, maybe lower cost, is Brandon Lowe. Either would be an upgade over Chisholm Jr., diary.
Conclusion: Others in Play
Some other free agent or trade aquisitions incude, Byron Buxton, CJ Abrams, Teruaki Sato ( a promising Japanese Third Baseman), Ketal Marte, Tyler Stevenson, Randy Arozorena, and Carlos Estevez (yet another option at closer). One thing is for certain, the Yankees need to be active this off-season and retake the fear they once inspired in opponents, diary. All these players are viable targets, now the Yankees just need to go out and get them.
Don't stop here
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