He was hired by John Schuerholz for his first big league gig with the Kansas City Royals in 1980, managed baseball operations for the office of then-Major League commissioner Fay Vincent, headed to the Atlanta Braves in 1991 and landed the general manager job with the Brewers in 1999.
He consulted with the Dodgers and MLB in 2003, was assistant GM for the Reds from 2004-05, and since 2006 he's been back where his Major League journey began, in Kansas City, as vice president of baseball operations and assistant GM to Dayton Moore.
Got all that?
Good, because Taylor and the Royals announced this week that the veteran of 39 (and soon to be 40) years in the Grand Old Game is going to transition into a quieter life of family, travel and relaxation. It's time for a change, but it's also time for Taylor and those who have worked with him and around him to express gratitude for an exemplary career.
"You make a lot of sacrifices in this game over the years," said Taylor, 63. "It's going to be great to have some private time to spend with my wife and son and grandchildren. A lot of us that are in this game for as long as I've been in it, I think, really need to give back to their families because we do make a lot of sacrifices.
"I'm very grateful to my family for how understanding they've been. But it's going to be time to step back and smell the roses a little bit -- enjoy the things that some of us in this game miss."
And the game will miss him.
"He's one of the more skilled administrators of an era," Moore said. "To me, he's one of the more highly skilled and respected baseball men of a generation, really. Thirty-nine years in the game, highly professional and highly respected. He was a huge part of the restructuring that we did when we came here and he really was highly instrumental in the programs we put in place at every level. He was really the rock of our front office."
Added Mariners GM Jack Zduriencik, who was hired by Taylor to be scouting director in Milwaukee: "Dean is such a gentleman. I thought he was always a very dignified person, a real classy individual who treated people with respect. People in turn respected Dean for what he stood for. He's just a good person, a very, very smart individual, and a really good administrator. He's meticulous, and that always impressed me. A very trustworthy guy. Very open. Very honest."
Moore remembers being in the Draft room at brand-new Turner Field in 1997 when the Braves, for whom Moore was assistant director of scouting, selected Troy Cameron with their first pick (29th overall) of the First-Year Player Draft. In the midst of all the chaos, there was Taylor -- impeccably dressed, calm and diligent, taking notes.
"It was the first time I'd seen him work," Moore said. "He was so detailed and prepared, and he was extremely locked in. From an administrative standpoint, he was just making sure everything was organized and going well."
All these years later, Taylor is the same way, and he'll continue to be that for the Royals in his grand finale of 2015, although he'll serve as more of a consultant and won't keep the all-day and sometimes all-night hours that his coworkers are accustomed to.
"He'll be a sounding board," Moore said. "He'll continue to provide guidance."
As for Taylor, he speaks of his career like one glorious whirlwind with highs and lows. He'll remember the highs. He ranks the Royals' 1985 World Series championship as a big one and also has to mention the Braves' worst-to-first season of 1991, which culminated in a seventh-game defeat to Minnesota in what's widely considered one of the greatest Fall Classics ever played.
He has similar emotions about the magic carpet ride the Royals just went on last October, with a loss in Game 7 of the World Series to the San Francisco Giants.
"I think '91 and truly 2014 were two years I'll always remember," Taylor said. "Both of those teams did something special that surprised a lot of people along the way. Both years were very gratifying from start to finish.
"It was gratifying to see for the Royals organization all the hard work that we put in since 2006, to see it come to fruition. These things are done successfully only with a complete group effort. Under Dayton's leadership, he was able to put together a tremendous group of people."
Perhaps none more respected than Taylor, although he prefers to deflect all the praise.
"It's been a great 40 years and I'm very excited for the fans here in Kansas City that were rewarded this year with at least an American League championship," Taylor said. "And we picked up a lot of fans throughout the country, so hopefully we're going to put an exciting club on the field next year."