This time around, Leyland will be trying to figure out a way to score some runs against his one-time prospect as Loaiza starts Game 2 of the American League Championship Series on Wednesday.
"He's had a very good career and gotten better with age," Leyland said of the 34-year-old Loaiza. "He's a very smart guy, a very confident guy, and he's a very tough guy. I couldn't be happier for him. He was a nice young man, and now he's a nice older man. He's really a good guy, he's learned his trade, and he's pitched extremely well."
The Tigers coaching staff is filled with former Pirates players and coaches, including third-base coach Gene Lamont, bullpen coach Lloyd McClendon, and hitting coach Don Slaught.
"It's every one except [Andy] Van Slyke," Loaiza said. "It's just one of the things that brings back memories looking at them now and what they've gone through in the past. Now they're all together, except I'm in a green uniform and they're in the Tigers uniform and we're battling for one thing, and that's going into the World Series.
"My respect for all of them," he added. "And whoever wins is going to the World Series -- I just wish everybody good luck."
Loaiza will probably take a different demeanor to the mound on Tuesday, as he enters the contest with an 8.00 ERA against Detroit.
"We're going to be facing a pretty strong team," Loaiza said. "They're a pretty aggressive team. I think I've just got to go out there and throw strikes, get the ball low and keep it in play. [I have to] try to get a lot of ground balls and keep the team in the dugout, and score some runs."
Loaiza pitched well in his first outing against the Tigers, allowing three runs over six innings on April 18. But on July 23, he was chased after three innings and was tagged for eight runs (five earned) on eight hits.
That first start against the Tigers was Loaiza's only quality start during April before he went on the disabled list with a strained trapezius muscle.
Loaiza had pitched in the World Baseball Classic for Mexico before the season and initially had trouble hitting the mid-80s with his fastball.
Loaiza earned the American League pitcher of the month award with a 4-1 record and 1.48 ERA in six starts. During three starts from Aug. 18-28, Loaiza didn't give up an earned run.
"The duration of the DL was probably lengthy [38 days]," said A's manager Ken Macha. "He went through a rehabilitation similar to what you would do in a spring training situation. I give Esteban credit. He was there on time. He did everything to the letter and to the tee."
"He could have easily just gone through the motions," added Macha. "But he wants to compete. He's a competitor, and he's showing that by the performance he had in the last two months of the season."
Loaiza started Game 2 of the ALDS against the Twins, and held them to two runs over five-plus innings. He threw five scoreless frames before giving up back-to-back homers in the sixth, but was more publicized for getting coffee spilled on him in the dugout.
Milton Bradley threw his batting gloves on the shelf of the A's dugout and accidentally knocked Loaiza's cup of coffee over. The coffee spilled all over Loaiza, who had to change uniforms and get a new glove.
"You could say I wore it," said Loaiza about the incident with laughter. "It was just one of the things that I didn't know how to react, but just to stay focused and stay in my plan of going out there and not paying attention to that."
Ryan Quinn is an associate reporter for MLB.com. This story was not subject to the approval of Major League Baseball or its clubs.