Ivan Rodriguez bolstered his prolific career in Detroit and helped mold a young pitching staff.
Magglio Ordonez hit the home run that landed the Tigers in the World Series in 2006 and won a batting title the next year.
Kenny Rogers became a fan favorite in Detroit en route to one of the most memorable postseason pitching stretches in recent memory and one of the more sudden image makeovers.
Bobby Seay, a Minor League free agent going into 2006, developed from an unfulfilled high-round draft pick to a veteran reliever.
Rick Porcello, a Boras client going into the 2007 Draft who later changed agents, has blossomed into one of baseball's brightest young pitchers.
Boras says he believes Johnny Damon can have a similar impact. He calls Damon a proven winner who can provide leadership, pointing to his two World Series rings. He considers it a very good fit, and it appears Tigers decision-makers are opening up to the idea.
"If there was an area we were going to address, it would be an offensive perspective," team president/general manager Dave Dombrowski said Thursday without mentioning Damon by name.
"I don't know if anything will happen or not. I really just don't know that. I think this is a time of year when you keep a feel of what's taking place. You can see guys are signing every day. Players are going to sign somewhere, generally. We'll just see what happens."
Whether the two sides can find the financial terms to make a deal, it's the latest chapter in the story of baseball's most famous agent and the Midwestern team that has invested frequently in his clients. It's sometimes pleasant, sometimes contentious, but it's rarely ever dull.
"The thing I like to say," Boras said Friday of Tigers owner Mike Ilitch, "is that Mike knows his investments. His businesses are successful."
Boras said much the same during the 2005 press conference in which the Tigers introduced Ordonez, who had just signed a guaranteed five-year, $75 million contract to jump from the White Sox. Ordonez was the last prominent free agent left on the market thanks to concerns about his surgically repaired right knee, and the Tigers were the last team looking for an offensive jolt.
A year earlier, Rodriguez was coming off a World Series title in Florida and concerns about how much longer he could continue catching before age would catch up. The Tigers were coming off a 119-loss season and were looking for any sort of credibility. Adding a star player, any star player, was the way to do it, and the Tigers had been spurned by one slugger after another.
For both player and team, it was the one logical fit left. Both of those negotiations seemingly took forever, and both ended with deals just before Spring Training.
What brought together those two deals was the Tigers' struggle to build a contending team in a city with a perception to overcome among players. The Tigers had to recruit as much as negotiate, and Ilitch was key in that effort, talking face-to-face with both players and telling them he was committed to win. Boras connected with that and connected directly with Ilitch.
"I think the goal of the club was to get to the World Series, and they did," Boras said. "And Mike Ilitch, at the time, probably paid for players. He did things that a lot of owners wouldn't do."
Now, with Damon probably the most famous free agent still looking for a job, the roles have shifted. The Tigers have three winning seasons in the last four years, and came within a game of the postseason in 2009. It's now Boras playing a recruiting role, positioning Damon as the potential piece that would put the Tigers back in command of the American League Central.
In that sense, his situation resembles that of Rogers, who was Boras' answer when the Tigers sought a veteran pitcher for its young rotation after the 2005 season. Detroit wasn't looking for a long-term commitment for an arm, not after watching Carl Pavano jilt the Tigers and suffer injuries that previous season. Rogers was coming off an incident with a television cameraman in Texas that helped end his time there and put into question whether anyone would take the public relations risk of signing him.
Rogers signed a two-year contract and responded with a 17-win season and an All-Star start in 2006. He didn't allow a run in 23 postseason innings that October. And the man who was booed at Comerica Park during the 2005 All-Star Game left the same field to standing ovations the next fall.
"I don't recommend players," Boras said, "unless I feel they can go there and do well."
He claims he feels that way with Damon. He points to Damon's World Series championships with the Red Sox in 2004 and the Yankees last fall as evidence he can help make the Tigers a winner. He also points to Damon's production, experience as a leadoff hitter, and his potential to allow the Tigers to use Austin Jackson in a less pressure-packed spot in the lineup. But Boras also points to the track record of his previous dealings with the Tigers.
Whether or not Damon becomes a Tiger, plenty of other Boras clients already are. Among them are Ordonez, Seay, Gerald Laird, Zach Miner, Max Scherzer and Jeff Larish, with draft selections Jacob Turner and Andrew Oliver in the farm system.
The endings aren't always easy. Besides last summer's suspense over Ordonez's option, Rodriguez's playing time became an issue before the Tigers traded him at the 2008 Trade Deadline. Injuries hampered Rogers after 2006, and he ultimately parted ways with Boras before signing a one-year with Detroit for 2008.
The Tigers won't need nearly the long-term commitment for Damon that they gave to Rodriguez or Ordonez, but they have to decide whether they would want a two-year commitment to Damon. If not, Damon and Boras might have to decide whether a one-year contract is enough.
If the two sides ultimately agree, they can only hope to have the same immediate dividends that previous dealings have brought.
"A lot of this is the fact is, that you get a lot of production for your investment," Boras said. "And when you get that, you're more likely to go back again."
Jason Beck is a reporter for MLB.com. This story was not subject to the approval of Major League Baseball or its clubs.