Since moving into the starting rotation in early May, the southpaw is 4-2 with a modest 3.39 ERA in the hitter-friendly venue that is the Pacific Coast League. Entering 2006, he had made only 27 starts in his 141 career appearances in the Cubs' farm system.
Injuries and/or call-up's to teammates always provided O'Malley with the chance to start in the past, and that was no different this season with Rich Hill, Angel Guzman and Jae-Kuk Ryu all getting the promotion to Chicago at one point or another.
"These past few years, it seemed like I always started from the bullpen and was in the rotation by the All-Star break," O'Malley said. "This is now my third stint in the PCL. A couple of years ago, I came up from pitching in relief at Daytona to starting here in the PCL. It was definitely a rude awakening."
But such has been the case for O'Malley at many a point and time in his career, and to say that the left-hander has always been an underdog may be a gross understatement.
After two up-and-down seasons as a pitcher for the University of Memphis, he signed as a non-drafted free agent in 2002 despite being told by several scouts that he could go as high as the first 15 rounds in the draft.
On the day of the '02 draft, when the Cubs were busy deciding on four first-round picks, O'Malley's name was never called. He thought it was the end of the line for his pitching career.
Four years later, after logging many innings in the bullpen and making the occasional spot start, O'Malley finds himself back in the role he became accustomed to in his latter two years of college. He transferred to Memphis in time for the 2001 college season and doubled as both a pitcher and outfielder with the Tigers after previously being a regular at first base with Lincoln Land Community College in his native Springfield, Ill.
As a pitcher, O'Malley has never showcased overpowering stuff. His four-seam fastball sits in the mid to upper 80s and he compliments it with a circle changeup, slider, and cutter.
But as O'Malley and everyone else knows, the fastest pitch is not always the best.
"I'm not a power pitcher that can strike out a bunch of guys," O'Malley admits. "There have been times in my career when I've tried to bump up and hit 90, but I'd rather know where the ball is going at 87. Just that 2-3 mph can make all the difference.
"I try to make something happen within the first four pitches of the at-bat – either get the batter to strike out or make contact. I'd rather make hitters earn their way on base. If they're going to get a hit or a home run, you just have to tip your cap."
A self-described control artist, O'Malley doesn't like the term "finesse pitcher" because he feels he throws enough fastballs not to be considered as such. In his first five starts this season, he walked only two batters and totaled 22 strikeouts.
He has since walked 13 in his last five starts, which he jokingly attributed to an Inside The Ivy jinx after we first asked about his strikeout-to-walk ratio following a late May outing against Nashville.
"I'm a control guy," he says. "So if I'm a control guy, it doesn't look very good if I have a lot of walks. There are percentages out there that tell you how many times a leadoff walk comes in to score and it's unbelievable."
Iowa manager Mike Quade has seen pitchers come and go in his three and a half years as the Cubs' Triple-A skipper, but few as memorable as O'Malley.
"What a guy," Quade says with a hearty, uproarious laugh. "When you look at his velocity, he's never going to be a guy who lights up the gun. His stature (6'1") is not that big, either, but he's been a tremendous addition here. He fills about any role you can ask. What can you say? He's a lefty."
O'Malley picked up his fourth win in the Iowa rotation on Thursday against the Omaha Royals, who are in a stretch of 17 consecutive games on the road due to their home field (Rosenblatt Stadium) playing host to the annual College World Series. He allowed four runs (three earned) in 5 2/3 innings, walking one and striking out three.
He won't be the first considered for a call-up, let alone a steady major league job, but for now, O'Malley is just happy for the opportunity to pitch.
"I've had to battle to make a team every year," he said. "But I look at it every year as though I still have an opportunity and have to make the best of it. I've been working hard and hopefully I'll get to the big leagues some day. Whatever the team needs, I'm their guy."
Added Quade, "It seems like he keeps pitching well at every level he goes through."