Toronto's left-handed reliever was a part of three different organizations -- Colorado, Arizona and the Cubs -- in just two months and was headed toward a year in the Minor Leagues before he finally had enough. Oliver retired in 2005 at the age of 34, but surprisingly didn't stay out of baseball for long.
A year removed from baseball, Oliver made his return to the big leagues with the Mets in 2006 and, arguably, has enjoyed the best years of his career since.
"I don't think I was ready to quit, but in this game you never really walk away when you want to, on your own terms," Oliver said. "You usually get pushed out and there's no job there for you. That's just the way sports is and I was really thankful that I got another chance."
Oliver's second life came as a surprise, even to himself. The former Ranger opted to make a pit stop at the 2005 Winter Meetings in Dallas to catch up with some old friends and swap stories.
Once there, he happened to have a conversation with Sandy Johnson and Bryan Lambe of the Mets. They asked if he was still interested in pitching, and while part of Oliver was reluctant, he also knew there was still a strong desire to play.
Oliver took a couple of weeks to make an official decision, but eventually signed a Minor League contract with the Mets. That was the start of a long road back to the Majors, as Oliver had to get himself back into playing shape following a season-long absence from the game.
"I ended up signing with the Mets, went on Jenny Craig for about a month, lost about 10 to 15 pounds and then went to camp and had a great spring," said Oliver, who is 112-90 with a 4.60 ERA in his career. "Some things had to happen in my favor. A guy got hurt in the last week of Spring Training and I ended up making the team.
"Next thing I know, I'm back in the big leagues with New York and what a great place to have a good season. We got into the postseason and I was able to parlay that into a contract with the Angels."
Oliver is now 41, but has posted the best ERAs of his 18-year tenure in the big leagues during the past four seasons.
The Kansas City native recorded ERAs in descending order of 2.88, 2.71, 2.48 and 2.29 during that span. Last year, Oliver struck out 44 and walked just 11 in 51 innings for the AL champion Rangers. He's also played in the playoffs six consecutive seasons with the Mets, Angels and Rangers.
Oliver's raw abilities may be in a decline, but the increased awareness he has on the mound has more than made up the difference.
"I think when you combine experience and age, with ability, they begin to know themselves that much more," Blue Jays manager John Farrell said. "He knows the league more, he knows which hitters can damage him and he'll pitch accordingly to minimize any potential damage.
"But what has been pretty remarkable -- not just that he has been able to improve each of the past four years and getting better with age -- when he transitioned full time to the bullpen he was with the Mets, his transition was seamless and almost a second career took off for him. I know in his case, he talks about how he knows himself and his abilities that much better."
The recipe for success has been relatively simple in Oliver's mind -- pitch ahead in the count and stay aggressive. Earlier in his career, Oliver often posted walk rates above 3.5 per nine innings, but over the past four years it has been lowered to an average of 2.2.
The end result has been an ability to extend his career beyond Oliver's previous expectations and a recent one-year contract worth $4 million with the Blue Jays and a club option valued at $3 million for 2013.
"One of the main things is just being consistent with my mechanics and throwing a lot of strikes, getting ahead in the count," Oliver said. "I can't really preach anything more than I can about getting ahead in the count. When you get ahead, you make guys swing at your pitch instead of them being able to wait for their pitch.
"If you get behind in the count, then bad things happen. So for me a big key has been staying aggressive and I've been blessed with some good teams, which obviously helps. Good defense -- you get that winning attitude and it's a lot of fun to play."
Oliver now joins a completely revamped Blue Jays bullpen, led by closer Sergio Santos and setup man Francisco Cordero. Oliver likely will be used mostly in the sixth or seventh inning in tandem with right-handers Casey Janssen and Jason Frasor.
The overall depth will provide Farrell with plenty of options in late-inning situations.
"How much we're able to use [Oliver], that will be determined. But I think having the ability to match up against the [Robinson] Canos, the [Adrian] Gonzalezes, turn [Ben] Zobrist around to the right side [will improve the team]," Farrell said. "A left-hander late in the game, and the success that he's had, -- I know when we signed him we got better, immediately."