Injured relievers like Neil Ramirez and Justin Grimm were getting healthy while the Cubs were adding from the outside. The writing was on the wall for Jackson. It was probably there going back to spring training when he was relegated to the bullpen. When Travis Wood joined him there, it was only a matter of time before a move like this had to be made.
What went wrong for Jackson? No one could pinpoint his problems as there were times his stuff was there. But more often than not he was a batting practice pitcher in a major league uniform. Cubs President Theo Epstein admitted early on that the team may have jumped the gun in signing him.
"Given the situation, I think we could have been more patient," Epstein said late in 2013 after Jackson went 8-18 in Year 1 of his four-year deal. "We could have been more in line with the plan. That said, when there is no pitching, you have to find pitching.
"I was being self-critical. Anytime you make an investment that doesn't immediately pay off, especially when you don't have tremendous freedom to make a variety of significant investments, you should be hard on yourself."
Epstein was more upset with his timing than the person, though if Jackson pitched to his contract, there would obviously have been less second-guessing. He had moments of success but they were few and far between.
"Things didn't turn out how I planned here," Jackson said. "It happens. It's the game of baseball. Even throughout the negative here, hopefully I was able to shed a lot of positive on a lot of people."
After each and every failed start, Jackson tried to answer the questions put to him while seeking his own solutions to his issues. Eventually, his responses started to repeat themselves, as did his poor performance on the mound. Then the boos from the home crowd came. The die was cast and there was no coming back from it for him.
If Jackson hadn't been a good soldier, he never would have lasted as long as he did. If he had taken his demotion to the bullpen in anger, things would have ended a lot worse. But that isn't Jackson, and besides, how could he be upset? The team gave him every chance to rebound from his problems, but after producing a 4.98 ERA in 2013, he followed that up with a 6.33 mark in 2014. The now 2015 contending Cubs had to move on.
"He's one of the best human beings I've ever been around," Jake Arrieta said Sunday evening. "It's hard to see him go. We were very close and our families are very close."
Arrieta had just beaten the Atlanta Braves with another masterful performance but his mood and the mood of his teammates was somber after the game. There were hugs and well-wishing tweets sent from pitchers and position players alike. Jackson even joked that someone else would have to take over the music in the clubhouse.
"I told Castro and Rizzo someone has to take it over," he said.
He handled failure with class but ultimately it was that failure that forced the Cubs to move on from a mistake. Signed before they were ready to win -- and for a lot of money -- Jackson won't go down as one of the front office's better moves. But he will be remembered as one of the finer people on the team.
"I wish him nothing but the best," Joe Maddon said. "First-rate human being."