Ilitch was a winner in hockey, having won Stanley Cups with the Red Wings. He had to convince Boras, Rodriguez and others he meant what he said.
Nine years later, Ilitch was on the podium with an American League championship trophy Thursday night for the second time in seven years. His Tigers who play in a city once named in player surveys among the least desirable places to play in baseball, were being lauded as a model organization that plays -- and spends -- to win.
"He just felt absolutely thrilled to be here, just to be part of this, and see what's taking place," team president/general manager Dave Dombrowski said.
Nobody was questioning his desire to win. In fact, as the Tigers await Game 1 of the World Series on Wednesday night at AT&T Park, on FOX at 8 p.m. ET, nobody figured he was satisfied.
The Tigers want this World Series for their owner.
"We realize what he's done for this team, what he's done for this city how much he invests into each sports team, the Wings and the Tigers," right-hander Max Scherzer said Tuesday. "I know getting so far in these playoffs puts a smile on his face. But I know at the end of the day, he wants to win it all, and that's what's great. ...
"As far as we've gotten, a lot of owners would feel proud. But he wants to win it all. There's no second place in his mind."
To hear Rodriguez, the first player who bought into it, he deserves to win.
"I think it's time for him, you know," Rodriguez said last week. "I think it's the year for him to have a World Series trophy in his hands. I think it's going to be great for him. He is going to feel very good about that and his family and all the work, all of the hard work that they have done, you know, since a long time ago ... to become the organization and the team that they have on the field right now.
"He deserves to be a world champion."
To understand the method behind Ilitch's madness is to understand the situation. He's 83 and he has made his money, starting with Little Caesars Pizza and branching into a booming entertainment industry downtown. When few wanted to invest downtown, he invested big, from the Red Wings to a theater, a restaurant and other venues.
Before he was an entrepreneur, before he was a hockey owner, he was a Minor League baseball player. He didn't have the ability to win then. He has the ability now.
"Mike's an old ballplayer, from way back," his wife, Marian, said in January after the Tigers signed Prince Fielder. "And he knows that when you have an opportunity, you have to take it. It's a big risk, and it takes a lot of guts, but he knows it's the right thing to try to win a championship."
Though nobody talks about life after Ilitch, as the old saying goes, he can't take it with him. As he heads toward his mid-80s, he has what he needs. His family is set. He's spending his money on what he wants.
"He's always there to give us really whatever we need and want, supports us all the time," Dombrowski said. "I remember he's told me all along, if there's one thing he really would love to have it would be that World Series ring. I remember we had that conversation 11 years ago when I joined the franchise, right around this time period. And so, hopefully, we can get that for him."
Most teams go into the winter with a budget. The Tigers go in with something more flexible. Dombrowski makes out the plan of attack to try to fill their needs, such as signing Victor Martinez two years ago, or drafting aggressively, or scouring the trade market this summer for a starting pitcher and a second baseman before finding both in the same deal in Anibal Sanchez and Omar Infante.
Ilitch lets his baseball people make the decisions on how to spend, with very few exceptions.
Trading for Miguel Cabrera five years ago and signing him to an eight-year, $152.3 million contract wasn't in the plans. Ilitch saw a chance to get a star, the kind his team had lacked for years, suggested Dombrowski see what it would take and authorized it.
When the Tigers went into last offseason, they had the plans to go big after Cuban outfielder Yoenis Cespedes. When Martinez's knee injury created a gaping hole in the middle of the Tigers' lineup, the plans changed.
Enter Fielder, with a nine-year, $214 million contract, the most resounding injury replacement in Detroit baseball history.
The Tigers entered the season with the fifth-highest payroll in baseball. They entered with less than the fifth-biggest media market. Their owner is not one to care about market.
He doesn't actively recruit anymore. He doesn't have to.
"I think this team in general has an amazing amount of respect for Mr. Ilitch and what he's done, not only for this ballclub but also for the city," Game 1 starter Justin Verlander said. "If he didn't put this ballclub together, this wouldn't be happening, and it wouldn't be this way for the city right now. ...
"He's the best owner in baseball. He's spared no expense in putting together this team. He wants to win. We want to win."