He followed up on that success by winning a combined 12 games and sporting a 2.55 ERA the following year between Lakeland (the Tigers' Advanced A affiliate in the Florida State League), Daytona (likewise the Cubs affiliate), and one late-season appearance at Double-A West Tennessee.
All in all for 2004, Connolly struck out 109 while allowing just 25 walks in his first year in the Cubs system. He had a career record of 34-15 with a 2.61 ERA in 74 games upon entering 2005.
Then, a shoulder injury, and less than a year later, Jon Connolly's stay in the Cubs farm system was over.
While pitching on an on-again, off-again basis at West Tenn last June, an MRI revealed a slight tear in his rotator cuff that required season-ending surgery and for Connolly (as is the case for all minor league pitchers rehabbing from arm injuries), the mandate to stay in Mesa, Ariz., during the long off-season winter months.
By Spring Training of this year, Connolly had resumed throwing. He says he was told by Cubs minor league officials within a week of his release that he would likely be held over in Extended Spring Training for roughly one month before being assigned to a full-season minor league affiliate.
At the time, the news was all well and good with Connolly, but then a funny thing happened. Seemingly overnight, the Cubs had a change of heart and gave the 22-year-old his walking papers: an unconditional release that the Cubs used to evoke the timeless "numbers game" response.
And so, on April 1, Connolly suddenly and without prior warning found himself packing his bags after spending over eight consecutive months away from his Oneonta, N.Y. home doing daily, often grueling rehab stints.
If Jon Connolly was going to be released by the end of minor league camp, he was the last one to know.
"Happy April Fools Day, right?" Connolly tried to pass off as a joke, but with an all too serious tone.
Connolly is no longer sure what his future holds in store. He'd obviously like to pitch somewhere and his career numbers would surely be impressive to most other farm systems. The question lies not within Connolly's performance on the field, but with his health.
He was recently invited to a tryout by the New Hampshire-based Nashua Pride of the eight-team independent Canadian-American League. (You may recall the Can-Am League is home to the fairly popular Brockton Rox in Brockton, Mass., the team owned in part by actor Bill Murray.)
Connolly must now play the waiting game as he awaits word from the Rox as to whether or not he is their newest member.
"The Nashua team called my agent and wanted me to go up and throw for them. The whole thing they and everyone else is wondering about is whether I'm healthy," Connolly reiterated.
"I'm still throwing as much as I can. I'm still working out and am trying to stay in shape. As of right now, I'm in the process of just trying to find a job, any job, whether it be baseball or something else."
And therein exists the dilemma Connolly faces should the Nashua Pride decide to take a pass on him. With no other profession besides baseball readily available to fall back on after being drafted out of high school at age 17 in the middle pack of the draft, college was never an option.
"I honestly don't even know what I would have gone to college for," Connolly now says looking back. "It was never something I put a lot of thought into back then."
Does he feel that he is healthy now?
"I feel that I am," he said. "The biggest thing is just getting an opportunity. I don't any have pain in my shoulder now, but I'm not quite all the way back yet. A lot of pitchers aren't until the second year after their operation."
While still with the Cubs this spring, there was never any doubt by the organization that Connolly was A-OK in terms of health, he says.
"The Cubs implied that I was healthy. They said it was a numbers thing as you know. I still don't really know what their thinking was there."
It goes without saying that one of the annual rites of passage each spring is minor league cuts. Many will likely point to Connolly's status as a finesse pitcher, coupled with the loss of what limited velocity he had to start with and no shortage of other pitching prospects in the organization as a means to cut ties with the southpaw.
Likewise, Connolly was never listed on the all-important top prospect ranking lists or given much national praise around the minor league community. All he did was pitch and pitch effectively for two different organizations in spite of not having the same flash or hype as many others in his age group.
It may be doubtful that anyone will ever kick up too much of a fuss about Connolly's departure per se, but isn't the purpose of the numbers game to distinguish players by the best possible statistics?
If so, given Connolly's track record, the Cubs have a funny definition for those "numbers."