That elusive ultimate title caps a 12-year stretch since Durham moved from the Advanced A Carolina League to Triple-A status, a period during which they've enjoyed nine playoff appearances, eight division titles, seven spots in the league finals, three IL championships and one national title (and a partridge in a pear tree).
Montoyo had a 10-year playing career mostly as a Minor League infielder from 1987-1996, getting the proverbial cup of coffee with the Montreal Expos for four games in 1993.
A manager in Tampa Bay's system for the past 13 years, the last three of which have come with Durham, he learned a lot during his playing career not just about how to play the game but also how to handle players -- and, really, how not to handle players.
That learning experience has made him one of the most respected and beloved managers in the game at age 44, and one whose teams have enjoyed a tremendous amount of success as a result.
The Bulls, still perhaps the most recognizable Minor League team in baseball 20 years after the release of the classic film "Bull Durham," finished '09 with an 83-61 record and the South Division title, second in the 14-team IL behind Louisville's 84-58 mark, but they eliminated the Bats in the first round of the IL playoffs.
Under Montoyo's guidance, Durham swept defending champion Scranton/Wilkes-Barre (Yankees) in three games to win its third Governor's Cup in 12 years and make it to the Triple-A title game in Oklahoma City.
There they faced the Pacific Coast League champion Memphis Redbirds (Cardinals) in a one-game winner-take-all title game, winning 5-4 in 11 innings in what had become typical Bulls-hustle style by scoring the winning run on a passed ball.
Did Montoyo know he'd have a championship team on his hands from Opening Day? If he didn't, he had a better idea after the slew of April roster moves and personnel changes didn't faze his crew.
"To tell the truth, the Opening Day roster doesn't matter that much because there's always so much movement," he said. "It doesn't matter if your team looks good in April. In Triple-A, if you can hang in there when your team isn't that good, when your good guys go up to the big leagues and you can win a couple of games then, that's when you have a good chance."
The team Montoyo and the Bulls broke camp with included names such top prospects as 2007 No. 1 pick David Price and Wade Davis on the mound and with veterans Chris Richard and Jon Weber in the lineup, but by the playoffs, the first three were in Tampa Bay and Weber was with Team USA winning the World Cup championship.
The knowledge that Triple-A is where all the changes occur, the players move up, the players move down, has taught Montoyo an important lesson: When scouting the opposition, he never looks at the team's record or even the standings. He only looks at their recent transactions.
"By the time you play a team, it's not the same team as it was earlier, so that's why I never talk about the other team's record," Montoyo said. "It's not because I'm superstitious."
But what Montoyo cares most about is his players. He remembers, 15 years later, what it was like to sit on the bench for more than a week without seeing his name in the lineup -- that uncertainty, that rustiness. He will not let his players feel that way.
"I always thought I'd be a decent Triple-A manager because, after five seasons at Triple-A, I know what it's like when you don't play," he said. "So on my team, everyone plays. No one goes more than two days without playing. Everyone gets their chance. I treat my team the way I wanted to be treated as a player."
Small wonder that so many six-year free agent veterans re-sign with the Rays and come back to serve as both key cogs in the lineup and team leaders in the clubhouse. Players such as Weber, who hit .302 before leaving to join Team USA, or Richard who hit .263 with 24 homers and 75 RBIs after being the team MVP in 2008.
And players such as closer Winston Abreu, who signed with the Rays prior to 2009 after spending '08 in Japan, and sandwiched around several weeks in the big leagues, posted a 1.94 ERA and limited IL hitters to a .133 average.
Those are the kinds of veterans who have helped out up-and-coming "blue chippers" such as Davis (3.40 ERA) and shortstop Reid Brignac (.282-8-44) and, later in the season, outfielder Desmond Jennings and Jeremy Hellickson, who came up from Double-A Montgomery and were named respectively the Rays' Minor League Player and Pitcher of the Year for 2009.
And while Montoyo couldn't necessarily have told you where his team was in the standings while the season was going on, he crunched the numbers after the summer ended and the stats he was proudest of were the ones that showed his team's clutch performances when it counted.
"In the playoffs we stole 28 out of 30 bases. We won 21 games in our final at-bats including the playoffs. We won 23 games where we were tied or behind after seven innings," he said. "We won 37 games when the other team scored first, including five out of seven times in the playoffs. And out of 15 extra-inning games, we had four games where we went into an inning where we had run out of pitchers and won the game."
Montoyo and his staff juggled the ever-changing roster with the aplomb of a Las Vegas headline act.
"A Triple-A team is by far the hardest team to manage because at that level we serve the big leagues and need to get those players to the big leagues first and foremost," said Mitch Lukevics, the Rays' director of Minor League operations.
And while Montoyo gives all the credit to his players, Lukevics gives the lion's share of the credit, unsurprisingly, to Montoyo and company.
"What the staff did there was extraordinary, keeping stability with that club despite who came and who left," said Lukevics. "That staff was the glue that kept it together all year long, the one constant. They always kept the right attitude, the right work ethic and the right message to our players."