NEW YORK -- In what Brian Cashman remembers as a series of his most difficult discussions with ownership, the veteran general manager received approval to dispatch several high-profile assets 2 1/2 years ago, having convinced managing general partner Hal Steinbrenner that his team was not strong enough to win the 2016 World Series.
Acting as sellers was foreign to the Yankees, who had not actively moved pieces in that fashion since dealing Rickey Henderson to the A's in 1989. They preferred the other side of those discussions, bolstering their postseason chances by adding stars from non-contenders, but Cashman points to Monday's acquisition of left-hander James Paxton as evidence that those bold non-waiver Trade Deadline moves are continuing to pay dividends.

In July 2016, the Yankees traded dominant left-handed reliever Andrew Miller to the Indians in exchange for four players, highlighted by outfielder Clint Frazier and left-hander Justus Sheffield. As the Mariners dangled Paxton this offseason, they refused to make the trade without obtaining Sheffield, who has developed into baseball's No. 31 prospect, according to MLB Pipeline.
"When we went to the marketplace with Andrew Miller back then to go through the rebuild, our initial interest and targets were trying to acquire high-end starting pitching back," Cashman said. "We were unable to thread the needle perfectly back then. We wound up with Sheff, who was further away with a high ceiling. Now he has closed the gap and is knocking on the door."
Sheffield is expected to be part of Seattle's youth movement, but the Yankees expect Paxton to be the high-end rotation piece that Cashman unsuccessfully tried to acquire at that 2016 Trade Deadline. Paxton was 11-6 with a 3.76 ERA in 28 starts this past season, tossing a career-high 160 1/3 innings while recording his first 200-strikeout campaign.
"Our window is as early as next year," Cashman said. "We have a 100-win team going up against the defending world champs, right in our division. … I fall back on the initial definition, when we traded Andrew to get multiple pieces back. It was to try and address the rotation. I still believe that deal is still giving and addressing in the near term."
Here is a look back at the Yankees' other significant moves during that period, all of which have impacted the Major League roster:
July 25, 2016: Albertin Chapman to the Cubs
Summary: Sending their flame-throwing closer to the eventual World Series champions, the Yankees centered the deal around touted infield prospect Gleyber Torres. Chicago added outfielders Billy McKinney and Rashad Crawford, plus right-hander Adam Warren, who'd been traded to Chicago by New York in the December 2015 Starlin Castro trade.

Outcome: Chapman helped secure the Cubs' first title since 1908, but Torres emerged as an All-Star this year, posting an .820 OPS in 123 games while finishing third in the American League Rookie of the Year voting. McKinney played two games with the Yankees this year, and then he was packaged with Brandon Drury in a trade to the Blue Jays for left-hander J.A. Happ, who went 7-0 with a 2.69 ERA in 11 starts down the stretch.
Referred to at the time by Cashman as a "lottery ticket," Crawford remains in the organization; the 24-year-old batted .234 this past season while appearing at three levels, playing 52 of his 81 games at Double-A Trenton. Warren posted a 2.35 ERA in 46 appearances in 2017 and had logged a 3.14 ERA through 47 outings this year before the Yanks dealt him to the Mariners in exchange for international bonus pool money.
July 31, 2016: Andrew Miller to the Indians
Summary: Six days after the Chapman deal, the Yankees parted with Miller, an All-Star who had pitched to a 1.39 ERA through 44 outings that year. In return, Cleveland dealt top-rated outfield prospect Frazier, the left-handed Sheffield, plus pitchers Ben Heller and J.P. Feyereisen.

Outcome: Miller helped the Indians reach their first World Series since 1997, as manager Terry Francona broke from convention by using him early in games for high-leverage situations. Sheffield anchored Monday's trade for Paxton, while Frazier was offered to the Pirates for Gerrit Cole last winter. He aims to exhibit what Cashman called his "legendary bat speed" as he recovers from post-concussion symptoms.
Heller owns a 3.00 ERA in 19 big league appearances with New York from 2016-17, and the righty hopes to return in July from Tommy John surgery. Feyereisen spent this past year at Triple-A Scranton/Wilkes-Barre, where the lefty had a 3.45 ERA in 37 appearances, finishing 13 games.
Aug. 1, 2016: Carlos Beltran to the Rangers
Summary: The 39-year-old Beltran was one of the Yankees' most productive hitters that season, but with only months remaining on his $45 million contract and promising prospects like Aaron Judge and Christopher Austin banging on the door, New York dealt the switch-hitter to Texas for right-handers Dillon Tate, Erik Swanson and Nick Green.

Outcome: Beltran's stats dipped in his 52-game cameo with the Rangers, with his OPS dropping from .890 with New York to .776 with Texas. As a free agent, he'd cross the state in 2017 to become part of the Astros club that toppled the Yankees on their way to a World Series championship. Beltran announced his retirement shortly after raising the trophy.
A former first-round pick, Tate made significant strides in New York's system and headlined a July 2018 trade for left-handed reliever Zach Britton. Swanson enjoyed a breakout campaign in '18, going 8-2 with a 2.66 ERA in 24 games (22 starts) at three levels of the chain before going to Seattle as part of Monday's trade for Paxton. Green was 8-7 with a 3.32 ERA in 23 starts for Class A Advanced Tampa and Trenton this past year.