Back in 2006, Cubs left-handed pitcher Ryan O’Malley was toiling at Triple-A. Growing up 200 miles south of Chicago in Springfield, Ill., O’Malley was doing something every young baseball player dreams about — playing for the team he grew up watching. Even if he wasn’t in the major leagues, he was still a member of the Cubs organization.
O’Malley didn’t throw hard or strike out a ton of batters. His arsenal was marginal, getting outs mainly by nibbling at the corners and not walking too many batters. After signing as an undrafted free agent in 2002, O’Malley bounced between the rotation and the bullpen at every stop along the way. A call to the big leagues seemed extremely unlikely.
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But on Aug. 16, 2006, O’Malley found himself on a big-league mound. What followed was a story of improbable success derailed by an unfortunately timed injury. Even though it only lasted a few days, O’Malley’s brief MLB story is one of the quirkier in recent memory. It’s a story that culminated in one strong outing against the Astros at Minute Maid Park, then became relegated to the ranks of obscure baseball trivia.
The story of O’Malley’s road to the majors ties in an interesting way to his good friend and former teammate, Rich Hill. The two came into the Cubs organization at the same time, and O’Malley describes their relationship as extremely close.
“Hill and I came in and went to the Boise Hawks together,” O’Malley told Sporting News. “We roomed together on the road, and we lived with host families together. Instant friends. We eventually hit every level together, in Lansing together, in Daytona Beach we lived together. We lived together in Jackson, Tennessee and Des Moines, Iowa.”
Hill made it to the big leagues for the first time in 2005, and unlike O’Malley was considered a serious pitching prospect. As fate would have it, Hill ended up playing a major role in O’Malley’s first — and only — call-up to the big leagues. The big lefty was scheduled to pitch that Wednesday afternoon in Houston, but the Cubs and Astros went 18 innings the previous evening. Chicago used six pitchers to get through the first eight innings, and Hill ended up on the mound to pitch the final two innings for the Cubs.
With no starter available to pitch the next day, the Cubs looked to their Triple-A team. As luck would have it, the Iowa Cubs weren’t too far away in Round Rock, Texas.
“I was having a really nice year at Triple-A, but Wade Miller was coming down to rehab and they were giving him my start,” O’Malley said. “… I wasn’t going to pitch that day, so they decided it was Ryan O’Malley going to big leagues. The stars lined up in an unbelievable way.”
The 26-year-old O’Malley hopped in a limo that morning and attempted to catch a few minutes of sleep in the back seat on the ride from Round Rock to Houston. Having been totally blindsided by the news, he wasn’t even aware who he’d face on the mound later that day. O’Malley had to ask his limo driver. The answer: Andy Pettitte.
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Len Kasper, then in his second season as the Cubs’ television play-by-play announcer, was hitting his stride with color analyst Bob Brenly at the time O’Malley got his call to the majors. After a somewhat slow start, Kasper had really endeared himself to Cubs fans. That game, so early in Kasper’s career in Chicago, will forever be one that fans associate with his emotional response.
“I don’t know if I knew much about Ryan at all, to be honest with you,” Kasper said. “One thing Bob and I talk about to this day is we were pretty worn out because we hadn’t slept much, and I think that made the game even more emotional. When you’re working on two or three hours of sleep, it’s a different kind of vibe.”
Kasper said that despite the exhaustion, O’Malley provided the spark the Cubs needed that day. A sixth-inning homer by Michael Barrett off Pettitte, who tossed a complete game, would be the only run scored.
O’Malley was oddly a bit wild that Wednesday afternoon in Houston, but he was just effective enough. He credits Barrett, a catcher with whom he had never worked, for helping him work through it. By nibbling the corners and not giving in to the Astros’ hitters, O’Malley finessed his way to eight shutout innings on 109 pitches.
O’Malley is just one of eight pitchers since 2000 to throw at least eight innings with zero runs allowed in his major league debut. That is some rare air.
“It was one of the better pitched games the Cubs had that year,” Kasper said. “Just at the end, he hugged his dad and he had shaving cream all over his face, his dad had shaving cream on his face and he’s crying. We got really emotional in the booth. Right when I signed off, Bob and I were basically crying.
“I’ve never ever experienced that before as a broadcaster and I don’t know if I ever will again. That game, of the thousands I’ve called in my career, still stands out as one of my favorites.”
Kasper knew something special had happened that day, and it wasn’t lost on O’Malley either.
“I’ll be honest, my stuff was never high-end stuff,” he said. “For me to get the opportunity that I did, the stars did have to line up that way. I don’t know if it ever would’ve happened otherwise.”
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After the game, the Cubs packed their bags to head back to Chicago for a six-game homestand against the Cardinals and Phillies. O’Malley knew he was packing his bag either way, to go back with the team to Chicago or to hop back in the limo and ride back to Round Rock.
It wasn’t until the Cubs’ traveling secretary came to him with his meal money for the week that O’Malley realized he was staying in the big leagues.
“You can’t put it into words,” O’Malley said. “I’m in the big-league hotel, I’m going to Wrigley Field, and I’m getting ready to continue to do my routine. Obviously it’s in a different place, but I just continued to work and got another opportunity.”
O’Malley’s next start came five days later against the Phillies and left-hander Jamie Moyer.
“A lot of emotions there, coming off such a high. But now, this is all real,” he said. “I was way more nervous for my Wrigley start than I was in Houston, because I had so much time to think about it.”
O’Malley pitched well enough against the Phillies, allowing just one walk and giving up three runs in 4 2/3 innings after a shaky first inning. But in the fifth, he felt a twinge in his left elbow.
“I didn’t feel anything until there was a ball that had a scuff and I lobbed it back to (catcher Henry Blanco),” O’Malley said. “At that point I was like, ‘Oh my God, what was that in my elbow? I’ve never felt that before.’ But no way am I saying anything, no way am I coming out of this game. This is my Wrigley Field debut.”
The next pitch O’Malley threw would be his last in the majors. Blanco, the veteran catcher, immediately knew something was wrong, and at that point O’Malley had no say in the matter. He was pulled from the game and would end up being yet another in a long line of Cubs pitchers in 2006 to be placed on the disabled list.
“I wasn’t on the disabled list once in my six years in the minor leagues,” he said. “For me to get the opportunity the way I did, to get that opportunity again, I didn’t really see it happening. And it never did happen again.”
After the season, Dusty Baker was fired and Lou Piniella was brought in as the new manager. The Cubs went on a spending spree, bringing in Ted Lilly and Jason Marquis to fill out the starting rotation. O’Malley got an invitation to spring training, but the writing was on the wall.
In 122 2/3 innings in the minors in 2007, O’Malley posted a 6.90 ERA with 25 home runs allowed. He would play just one more season, in the White Sox organization, before stepping off the mound for good.
“The fact that he hadn’t gotten to the major leagues until that moment, that rare weird circumstance, he was going to have to be almost perfect to stay,” Kasper said. “You see it occasionally with guys getting the opportunity, even if it’s a great performance you just never know how many other chances you’re going to get. So once he got hurt, it was going to be a very big hill for him to climb to get back.”
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Next came a brief stint in coaching, first with the Rangers and then with the Angels. But despite enjoying the work, O’Malley knew he had a choice to make.
“At that point I had met my wife and we got married and were ready to start a family,” he said. “Through the years of playing and seeing coaches and players with families, it’s not the best atmosphere to raise a family. I always knew that there was going to be some point where I’d need to have a different lifestyle.”
The O’Malley family settled down in Phoenix, where they still live. O’Malley enjoys watching games and just being a fan, while still getting to look at the game from a player’s perspective. He makes a point to get together with Hill any time the Dodgers are in town. O’Malley speaks glowingly about Hill’s late-career resurgence, even admitting to rooting for his friend over his beloved Cubs in the 2016 NLCS.
Although he misses the minutiae of life as a baseball player, O’Malley is content with the life he has built post-career. He’s at peace with how his career ended and is able to comfortably look back on everything that happened during his brief MLB experience.
Even if he didn’t get another chance in the big leagues, nobody will ever be able to take away the day he outdueled Andy Pettitte in Houston.
“I couldn’t be happier,” O’Malley said.