He pitched for the Padres during heated games within the National League West against the Dodgers and Giants. The right-hander also worked briefly for the Brewers at the end of the 2007 campaign, getting an up-close and personal look at the Milwaukee-Cubs battle.
Nothing, though, has prepared the veteran hurler for what he is about to experience, beginning Friday afternoon at Wrigley Field.
"I just heard they broadcast the batting practice live on television. I can't believe that," said Linebrink of the first game of the Crosstown Showdown between the Cubs and White Sox. Linebrink spoke Thursday after pitching one scoreless inning as part of a 13-8 drubbing of the Pirates before 26,685 at U.S. Cellular Field.
"Why would anyone want to watch batting practice?" added Linebrink with a laugh. "It's always fun to play in an atmosphere like that. It will be big. I'm looking forward to seeing it."
Judging by the results from the past three days, the White Sox (41-31) are going in on a high note while the Cubs appear mired in their first true funk of this highly successful season to date. The South Siders prepared by disposing of the hapless Pirates (34-39), a team which certainly will avoid Chicago as any sort of future vacation plans.
Factoring in Thursday's output, the White Sox outscored the Pirates by a 37-14 margin, to raise their Interleague mark to 7-2. Three more home runs against starter Phil Dumatrait (3-4) and reliever John Grabow gave the White Sox 10 for the series, and their 15 hits raised the White Sox team batting average in June to .316, with 115 runs scored.
Just for the challenge of it, the South Siders even overcame a six-run second deficit to complete the three-game sweep. A Pablo Ozuna throwing error with the bases loaded extended the second inning, and Gavin Floyd (8-3) yielded six unearned runs before he was able to get the third out.
"After the error, I made some bad pitches," said Floyd, who allowed one earned run over 5 2/3 innings, before Matt Thornton replaced him after 101 pitches. "But I really felt like I got stronger as the game went on, and felt better."
"Are we just gonna give up after being down six?" added White Sox first baseman Nick Swisher, who had one hit and scored one run. "No. We just battled our tails off. Floyd battled for us. He kept them right there, and obviously, we had the big inning just like they did."
That big inning actually came in the bottom of the second, when the White Sox scored six times off of Dumatrait. Jim Thome started the rally with a leadoff double, scoring on Jermaine Dye's ensuing double. Alexei Ramirez and Ozuna singled home the second and third runs, before Orlando Cabrera finished the comeback with a three-run blast to left field.
Cabrera has three home runs in his last six games and has hit safely in 16 of his last 17. The White Sox shortstop drove in four runs, but it was Dye who tied a career high with six RBIs. Dye launched a home run in the third to give the White Sox the lead, and then hit his seventh career grand slam in the seventh off Grabow to cap his mighty offensive showing.
Dye's average sits at .340 over his last 14 games, with five home runs and 15 RBIs. He was just one of the many White Sox hitters up and down the lineup pummeling the Pirates' pitching staff into submission.
"They're a good hitting team," Pittsburgh outfielder Nate McLouth said. "You have to give them credit. They hit the ball, what are you going to do?"
"We have been up and down, but the last couple of days at home, we have swung the bat well," added Dye, who now has 14 home runs and 38 RBIs. "Hopefully, it will carry over on the road now."
Of course, the first leg of the White Sox upcoming six-game road trip takes them eight miles north. Both teams will be in first place at the start of a series for the first time in the history of this intense rivalry, with a chance for the Cubs to match the White Sox 4 1/2-game lead in the American League Central on Thursday night in St. Petersburg.
Both teams also have pummeled the Pirates this season, to the tune of a combined 1-8 record (Cubs are 5-1). So, who do the Pittsburgh players think has the advantage in this upcoming competition?
"I don't know," Dumatrait said. "They can both swing it. They can definitely both swing it."
"They're comparable," Pittsburgh shortstop Jack Wilson added. "Good pitching staff. Very good defense. They've got hitters. I'd say they're very close to their neighbors."
That final decision will be made on the field this weekend and next weekend at U.S. Cellular Field. Then again, maybe the two teams will face off again in October, with a much bigger prize on the line.
At this point, the White Sox are simply looking to win another series amidst a frenzied playoff atmosphere that players such as Linebrink will experience for the first time.
"This is gonna be huge, regardless," Swisher said. "We feel good. Obviously, we got some banged up guys, but they do, too. It's going to be fun. The place is going to be electric. And we're ready for it."
"Really, it's almost like a payoff atmosphere, and it's great for the city," Thome added. "I'm sure a lot of memories will come this weekend to add to the list."
Scott Merkin is a reporter for MLB.com. This story was not subject to the approval of Major League Baseball or its clubs.