NEW YORK -- Facing roster crunches brought on by their incoming Draft class, the Orioles on Monday released Evan Phillips and Cody Carroll, ending the tenures of two pitchers brought into the organization during the earliest stages of its rebuild. The club also released outfielder Chris Shaw and two other Minor Leaguers; Phillips, Carroll and Shaw had been at Triple-A Norfolk.

The timing comes slightly more than three years since Phillips and Carroll arrived in the organization amid a flurry of trades by then-GM Dan Duquette, which stripped the big league roster of core players with expiring contracts as the Orioles began positioning for a long-term rebuild. It’s at least unwise -- if not impossible -- to judge such deals in the moment, given the number of prospects involved and the time it takes for each prospect to develop.

But ample time has passed now to warrant reflection. Of the five regulars the Orioles dealt at the time, only one remains with the team to which he was traded. And of the 15 players (14 prospects) Baltimore acquired, more than half are no longer with the organization. Most of the others have reached the Majors or are close to doing so.

With that as a backdrop, let’s look back on those deals one by one:

Orioles traded to Braves: RHP Kevin Gausman, RHP Darren O’Day
Orioles get: LHP Bruce Zimmermann, RHP Evan Phillips, OF JC Encarnacion, C Brett Cumberland

Zimmermann was considered a throw-in among the four prospects acquired, but he now has the best long-term projection of the bunch. Phillips and Encarnacion are no longer with the organization, and Cumberland, 26, remains at Triple-A, with Adley Rutschman looming. Zimmermann earned a rotation job this spring, went 4-4 with a 4.83 ERA in 12 games (11 starts), and is expected back this month from left biceps tendinitis.

Gausman, meanwhile, was excellent for Atlanta down the stretch in 2018, but he struggled the following season and bounced around, first to the Reds and then the Giants. He blossomed into an All-Star this season at age 30, for the first time in his career. O’Day, now 38, was limited by injury to 39 games over the past three seasons.

Orioles traded to Yankees: LHP Zack Britton
Orioles got: RHP Dillon Tate, RHP Cody Carroll, LHP Josh Rogers

Three years after this deal, Tate is the only pitcher remaining in the organization. Rogers and Carroll have been released, logging 26 big league games between them. Tate debuted in 2019, and after some ups and downs, he seems to have found his footing a bit in middle relief. The former No. 4 overall pick (2015 Draft, Rangers) owns a 3.71 ERA and a 1.07 WHIP in 49 games over the past two seasons.

One of the most accomplished relievers in Orioles history, Britton continued to put up superb numbers in the Yankees' bullpen until being sidelined for most of 2021 with injury.

Orioles traded to Dodgers: 3B Manny Machado
Orioles got: RHP Dean Kremer, OF Yusniel Diaz, INF Rylan Bannon, RHP Zach Pop, INF Breyvic Valera

This was the biggest of the Orioles’ deals at the 2018 Trade Deadline, and it’s looking increasingly one-sided. Pop and Valera are no longer in the organization, Bannon has plateaued at Triple-A and Kremer is back there after struggling mightily in the big league rotation. The prize of the deal at the time was Diaz, whose development has been continuously slowed by injury since arriving from the Dodgers’ system. Limited to 22 games at Norfolk this season, Diaz, now 24, has been nursing a right toe issue since July 11. It’s growing less clear if he’ll debut in the Majors this season, despite his presence on the 40-man roster.

Machado helped the Dodgers to the 2018 World Series and signed a 10-year, $300 million free-agent deal with the Padres before the '19 season. He was an All-Star this year, for the fifth time.

Orioles traded to Brewers: 2B Jonathan Schoop
Orioles got: 2B Jonathan Villar, INF Jean Carmona, RHP Luis Ortiz

Of their four major deals at the ’18 Trade Deadline, this is the only one the Orioles objectively won (if extending Schoop was not a possibility, which it wasn’t). Schoop was a non-factor for the Brewers down the stretch, playing sparingly during their run to the NLCS that October. He then went on to have three productive seasons for the Twins and Tigers.

The Orioles got one excellent season from Villar in 2019, but when it became obvious they weren’t going to tender him a contract, they were only able to parlay that into a depth prospect (left-hander Easton Lucas) in a trade with the Marlins. Ortiz was out of the organization within a year, and Carmona is 21 and in A ball.