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June 27: Yanks’ potential outfield targets
If there’s one area the Yankees need to upgrade more than any other prior to this year’s Trade Deadline, it’s the outfield. Although Aaron Judge is a leading AL MVP candidate and Giancarlo Stanton is on pace for more than 35 homers, the combination of Joey Gallo and Aaron Hicks has produced a .198/.310/.318 slash and an 88 wrC+ over 432 plate appearances.

MLB.com's Mark Feinsand looked at potential fits for some of this year's top trade candidates on Sunday and listed the Yanks as possible suitors for the Cubs’ Ian Happ and the Pirates’ Bryan Reynolds.

Happ (controllable through 2023) mostly has played left field this season, but he has extensive experience in center, too. The 27-year-old switch-hitter owns a .279/.376/.459 slash with eight homers over 71 games. Happ will likely cost less to acquire than Reynolds, who is under team control through 2025. 

Reynolds, 27, has rebounded from a slow start to hit .333/.374/.556 with five homers in June. He had a .302 average and .912 OPS in 2021, both better than Happ’s personal-best numbers in those categories (.264 BA, .898 OPS in 2019).

Reynolds also has shown the ability to be an excellent defender in center, recording +9 outs above average last season, though he hasn’t been as strong this year (-3 OAA).

June 25: Yanks planning to make run at Castillo?
The Yankees have the best record in MLB, as well as the game’s best team OPS and second-best ERA, so the club doesn’t necessarily need to make a big splash at this year’s Trade Deadline. But with a World Series championship drought going on more than a decade, which is an eternity in the Bronx, a blockbuster trade can’t be ruled out.

In an article for The Athletic (subscription required), Peter Gammons reports that a number of likely Trade Deadline sellers have been scouting the Yanks' farm system under the assumption that general manager Brian Cashman is going to be in the market for a big-name starting pitcher, such as the Reds’ Luis Castillo or the A’s Frankie Montas.

The Yankees have had internal talks about Castillo, per Gammons, though it’s unclear if they’ve opened trade talks with Cincinnati yet. Gammons expects the market for Castillo and Montas to be robust, with the Dodgers, Blue Jays, White Sox, Mets, Astros and Giants all in the mix to land one of them.

Like Montas, Castillo is under control through 2023, so it will take a strong package to acquire him from the Reds.

Last summer, the Blue Jays traded two MLB Pipeline Top 100 prospects -- infielder/outfielder Austin Martin and pitcher Simeon Woods Richardson -- to the Twins for righty José Berríos, who had an extra year of control remaining at the time of the deal. Berríos was 27 when the trade went down, while Castillo is now 29. But the two are otherwise very similar.

• Berríos, 2018-21 (pre-trade): 3.73 ERA, 3.84 FIP, 9.21 K/9, 2.65 BB/9
• Castillo, 2019-22: 3.62 ERA, 3.55 FIP, 10.02 K/9, 3.53 BB/9

According to Gammons, the Reds have looked at Yankees No. 27 prospect Will Warren. The right-hander was an eighth-round Draft pick in 2021, but he’s already pitching at Double-A and has developed a wicked slider and added velocity under the Yankees’ tutelage.

June 13: D-Rob back in the Bronx?
David Robertson already has had two stints with the Yankees in his 14-year career. Could we see a third? In an article for the New York Post on Saturday, MLB Network insider Joel Sherman mentioned Robertson as a potential Trade Deadline fit for the Bronx Bombers.

After undergoing Tommy John surgery in 2019 and making just 19 appearances across 2019-21, Robertson has had a strong season for the rebuilding Cubs, posting a 1.59 ERA with seven saves and 32 strikeouts over 22 2/3 innings. The 37-year-old signed a one-year, $3.5 million deal with Chicago in March, so he can become a free agent after this season.

The Yankees have the best record in baseball and will surely be a Trade Deadline buyer this year, but it’s not a given that they’ll be overly aggressive, according to Sherman.

New York’s starting pitching has been excellent this season, so it’s unlikely the team will pursue A’s right-hander Frankie Montas, barring an injury to one of its top starters. And while the team has gotten modest offensive production from the catcher spot, Cubs backstop Willson Contreras is another unlikely option for the Yanks, who like what Kyle Higashioka and Jose Trevino are providing on defense.

In addition to Robertson, Sherman considers Royals left fielder Andrew Benintendi and Nationals center fielder Victor Robles to be more realistic targets for Yankees general manager Brian Cashman.

June 4: Report: Andújar requests trade
The Yankees enter Saturday with the best record in baseball and few glaring flaws. However, not everyone definitely wants to stick around. As first reported by Z101 Digital's Héctor Gómez and confirmed by The Athletic's Ken Rosenthal, infielder-outfielder Miguel Andújar has requested a trade. More >

May 19: NL team exec wouldn't be surprised if Yanks deal Gallo
MLB.com's Mark Feinsand recently asked front-office executives across baseball which teams they think will be selling at this year's Aug. 2 Trade Deadline and which players are most likely to be moved. Among the bevy of players mentioned, the "most intriguing name," according to Feinsand, was Yankees outfielder Joey Gallo.

Gallo, acquired from the Rangers as part of a six-player swap last July, has slashed .166/.299/.379 with 18 home runs and 29 RBIs in his first 93 games with New York, including .176/.294/.333 with five home runs and seven RBIs in 35 games this season.

"There’s some Sonny Gray feel to that one,” an NL executive told Feinsand. “He’s been a little better lately. If he continues to struggle it wouldn’t surprise me to see them try to flip him.”

Gray compiled a 3.52 ERA (114 ERA+) and made one All-Star appearance in five seasons with the A's before he was sent to the Yankees at the 2017 Trade Deadline for three of New York's top 10 prospects. However, the right-handed starter struggled in the Bronx, recording a 4.51 ERA (96 ERA+) through 34 starts. He was dealt to the Reds prior to the 2019 season.

On the bright side for Gallo, he entered Wednesday with a 50.1% hard-hit rate, his best since 2019. And his expected slugging percentage (.542) is more than 200 points higher than his current mark. The 28-year-old is slated to become a free agent this winter.