Two years ago, the Cubs wanted to see if Brett Jackson and Josh Vitters would sink or swim, hoping they could stay afloat in the big leagues. They didn’t.
Now, both players have become cautionary tales for putting lofty expectations on unproven prospects.
As the Cubs integrate top young players like Javier Baez and Arismendy Alcantara, they parted ways with Jackson late Thursday night, dealing him to the Arizona Diamondbacks in exchange for 26-year-old pitcher Blake Cooper.
“We were gonna have a roster crunch coming up," Cubs general manager Jed Hoyer said. "We’re sort of trying to get ahead of that a little bit. Sometimes, it is change-of-scenery time. It had been two straight years at Iowa where he had been struggling. I wish him luck. Hopefully, it is a good change of scenery for him.
“Here, it was probably going to be a situation where we were going to have to take him off the roster and we were able to work out a deal with Arizona and get something done ahead of that decision.”
Jackson, now 26, was a first-round pick in 2009 and had been ranked as Baseball America’s No. 32 overall prospect prior to the 2012 season. He has never made it back to the majors after that 44-game stretch at the end of 2012.
After hitting just .175 with 59 strikeouts in 120 at-bats with the Cubs, Jackson got sent back to the minors to start 2013, but couldn't solve his contact issues and wound up being demoted to Double-A Tennessee to close out the season.
"From the beginning, I've always thought that I'd always be a Cub," Jackson said in early July. "I think that's where my mentality [has stayed]. The Cubs have been really good to me. They've believed in me when I've been at the bottom of the bottom.
"I'm very grateful for the Cubs. I'm very proud to [have worn] their emblem on my chest. What happens from here on out the rest of my career isn't really up to me. I'm just trying to prepare every day to get back to playing the way I think I'm capable of playing."
Jackson hasn't seen regular playing time this year as the Cubs have transitioned a new generation through the farm system, one led by Baez, Kris Bryant and Addison Russell.
At the time of Thursday's deal, Jackson was hitting .210 with a .646 OPS in 81 games at Triple-A Iowa. The power-speed combination that made him such an intriguing prospect was all but gone, with only five homers in 224 at-bats and four steals in 10 attempts.
Jackson said in last month’s interview that he still had visions of winning it all in Chicago and hoped to stay with the Cubs forever. He didn't feel he needed a change of scenery to get his career back on track.
Jackson's shadow will linger over the organization after his departure, serving as a reminder that not every young player on Baseball America's rankings will turn into a star. The Cubs won't hit on all these new top prospects.
During his four-and-a-half months at Iowa this year, Jackson saw Baez and Alcantara promoted and watched as Bryant came up and continued to rake, all the while knowing the true weight of being a face of the future for a franchise that hasn't won a championship in more than a century.
"I've experienced a lot of what they're experiencing, going through the whole top prospect thing," Jackson said. "How to handle the media, how to handle the fans and what it's like to have that pressure of being the savior for Chicago on your back and how you push that aside and take care of your business.
"Do what you can do to help the team win, and what happens at the end of the day, happens. Obviously, those are really tough things to live up to, but that is part of being a Cub."