The 30-year-old southpaw spent seven losing seasons in Pittsburgh, posting a 53-73 record, unable to post a winning record as a starter in any year.
Things have brightened a little on a personal level for Maholm this year after signing with the Cubs in January. He leads the club with eight wins, just two shy of his career high, and his 4.09 ERA is an improvement over what he posted in the majority of his seasons with Pittsburgh.
But just as he did so many times with his former club, Maholm has spent most of this season far from first place in the National League Central.
On Tuesday, Maholm will face his former team, whose fortunes have flipped this season, thanks in part to Tuesday's Pirates starter, James McDonald. If Maholm can't play for a winner just yet, he wants to do the next-best thing -- play spoiler.
"I hope they do well, and I hope we come in and spoil it a little bit for them," Maholm said. "The fans deserve a winner. We'll see how the three days go when we're there. Obviously, I hope we beat them and kick them back in the standings a little bit."
That hasn't been an easy task for opponents recently, as the Pirates entered Monday riding a five-game win streak and fighting for contention in the NL Central.
The Cubs broke Pittsburgh's win streak with a tight 2-0 win Monday, and if Maholm continues to pitch like he has throughout July, Chicago may begin a streak of its own.
Maholm is 3-0 with a 1.23 ERA in three starts this month. He lasted at least six innings in all three outings and allowed a combined three runs on 19 hits.
"When he's been going out there, he's had all four pitches working," Cubs manager Dale Sveum said of the left-hander. "He's moving the ball in and out, he's back-dooring his cutter, he can flip his curveball in there for a strike and he can bounce it. He's sticking to the game plan we've put together, he's not shaking off and he's just doing a great job with all his pitch selection."
Maholm has faced his former club once already this season, back in May. He allowed two runs on four hits in five innings and received a no-decision in the Cubs' 3-2 loss.
"It's different because those guys have seen me pitch for so long and I've only pitched against them once," Maholm said. "It's always kind of a cat-and-mouse game. I didn't have very good stuff the last time I went there. Hopefully, I can keep pitching how I've been pitching and see how it goes."
McDonald, meanwhile, has lost just once since May 11 but has surrendered four or more runs in three of his last five starts after holding the opposition to three or fewer in each of his first 16 outings this year. The right-hander earned the win his last time out, at Colorado, despite allowing six runs on nine hits and four walks in five innings.
"You never know what can happen in this park," McDonald said of Coors Field. "You can get runs quick. They were playing their tails off behind me, so I had to keep competing. "
Cubs: Uncertainty hovers over Garza
Right-hander Matt Garza has been one of the main talking points in Chicago recently. He was pulled from his Saturday start at St. Louis after just three innings because of cramping in his right elbow. He was feeling better on Monday, but Sveum said Garza will likely be skipped in the rotation for at least one start.
"There's some improvement," Sveum said Monday. "[His arm is] not quite extendable, but he doesn't seem to be concerned about it. I think [Tuesday] will be the big day to do the evaluation. That's when we'll have to make some decisions and line up stuff."
Garza, 5-7 with a 3.91 ERA in 18 starts this season, was scheduled to start on Friday, but Sveum said Travis Wood will likely fill in after the Cubs take their off-day Thursday.
Garza will not throw a bullpen session Tuesday. While nursing his arm and awaiting word on his next start, the righty has also been involved in trade rumors.
The Dodgers are reportedly interested in the seven-year veteran, with a report on Monday saying Los Angeles would trade righty Zach Lee -- the No. 1 prospect in the Dodgers' farm system, according to MLB.com -- to the Cubs in a package deal. Garza would be under team control through 2013.
Pirates: Bullpen thriving
Entering Monday, Pittsburgh's bullpen led the Majors with 35 saves and an 85.4 save percentage (35-of-41).
The unit has surrendered just one run in its last six games, spanning 15 2/3 innings.
"I kind of expect them to be [successful]," said manager Clint Hurdle. "They want to do well. They prepare. They focus. I just am a positive guy. When I send them out there, I'm looking for them to get outs. They're looking to get outs."
Andrew McCutchen has reached base safely in 35 straight games against the Cubs.
Since June 25, the Cubs are third in the NL with a .652 winning percentage (15-8).