Sunday was a bittersweet day for Jameson Taillon and the end of an era for the Pirates.

When he was drafted second overall in 2010, between Bryce Harper and Manny Machado, Taillon imagined pitching at PNC Park someday for a playoff-bound team. Before he was called up to the Majors in 2016, he looked around the Triple-A Indianapolis clubhouse and thought that group could get the Pirates back to the postseason.

But Taillon’s time with the Pirates ended on Sunday with the club at the outset of a rebuilding phase and without him throwing a pitch in the playoffs for Pittsburgh. As general manager Ben Cherington continued his efforts to add talent to the farm system, the Pirates traded Taillon to the Yankees for four prospects: right-handers Miguel Yajure and Roansy Contreras, outfielder Canaan Smith and shortstop Maikol Escotto.

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“It’s a perfect opportunity. I’m, like, giddy about it,” Taillon said in a phone interview. “I’ve put in a ton of work over the last couple years to reinvent myself and put myself in position to contribute to a team like this. I’m ready to come in and get to work.”

When former Pirates GM Neal Huntington famously spoke about a “bridge year” entering the 2016 season, he was talking less about taking a competitive step back and more about bridging the gap from the Andrew McCutchen/Gerrit Cole-led team to a roster potentially propelled by near-ready top prospects such as Taillon, Tyler Glasnow, Josh Bell and Austin Meadows, among others.

That group didn’t pan out for a variety of reasons. Some weren’t developed properly in the Pirates’ system. The club traded away others, like Glasnow and Meadows for Chris Archer. A few were dealt bad luck, none more so than Taillon as he battled through testicular cancer and two Tommy John surgeries.

“It’s kind of bittersweet,” Taillon said in a phone interview. “When I got drafted by the Pirates, you dream of coming up with the guys you get drafted with and come up through the system with. You dream of winning with them and bringing that to Pittsburgh. Over time, guys start leaving, guys get traded, guys retire, guys get released, stuff starts happening. … I feel like this is kind of the conclusion of that. We never proved we could win together.”

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Without sufficiently supplementing that group, the Pirates struggled through losing seasons four of the past five years and turned over much of their leadership following the 2019 season. After evaluating the state of the organization during his first year as general manager, Cherington decided this offseason to more aggressively pursue prospects and prepare a potential contender years down the road. That led to the decision to trade Bell, then Joe Musgrove and now Taillon.

“It was more clear to us that, to get to where we really wanted to go, we just need lots more players and lots more opportunities,” Cherington said Sunday. “They’re not all going to turn out. Not all the players in the Minor League system before these trades are going to pan out, but we just need lots of them, and then we’ve got to really pour into development. Especially in deals like this, the acquisition is one half of it, and the development is just as important. We’ve got to pour into that now.”

There is a difference between appreciating that plan, sensible and overdue as it may be, and enjoying the execution of it. Bell and Musgrove were popular in Pittsburgh. Taillon represented the franchise on and off the field as well as anyone could ask. They’re gone now, and the Pirates are at the beginning of what could be a long road toward building their next competitive team.

“I think they have the right people in place to get the job done,” Taillon said “I’ve told everyone I talked to with the Pirates organization that today. I know people are probably getting tired of hearing it. Pittsburgh has been wanting a winner for a long time.”

Taillon praised the work ethic of the Pirates’ leadership -- notably Cherington, manager Derek Shelton, pitching coach Oscar Marin, bullpen coach Justin Meccage and the analytics department.

“They’re moving in the right direction, and the right people are in place,” Taillon said. “It’s just going to take time, which sucks, but it’s a room full of dudes that are hungry. Nothing but the best for them.”

The Pirates didn’t enter the offseason planning to move Taillon, who praised Cherington for keeping him “super in the loop” throughout the process. They kept an open mind and listened to offers, including persistent interest from the Yankees all winter, but they expected to keep him on board. Then interest intensified after they traded Musgrove, and New York’s offer was significant enough to get a deal done.

“We would hope this one works out well for everyone: Pirates, Yankees, Jamo, the players we’re getting back,” Cherington said. “That’s the best outcome we’re looking for -- that this ends up well for everybody.”

Why not wait to move Taillon, who is due $2.25 million this year and is under club control through the 2022 season? It’s worth noting that he’ll likely have an innings limit returning from his second reconstructive elbow surgery, perhaps lessening teams’ interest if they were uncertain about his workload down the stretch. An early injury or ineffectiveness could have sunk his trade value, too, as he inched toward free agency.

“We just tried to factor all of that in the best we possibly could, comparing what was on the table now to what we felt like could be down the road, given a sort of reasonable expectation of a return and performance,” Cherington said. “We just felt like this made sense for us right now.”

Now the Pirates will pivot toward adding veterans to fill the holes on their roster as they prepare for Spring Training. They’ll keep an open mind if anyone comes calling with further trade proposals. And Taillon will move on to New York, once again envisioning a future in which he and Cole pitch atop the rotation of a playoff-bound team, while the Pirates work to build one of their own.

“This organization’s become family to me, and they stuck with me through a lot -- a lot,” Taillon said. “I don’t know if ‘regret’ is the right word, but I wish I could have put it together a little bit more and proven what I could do with Pittsburgh. Great city, great organization.”