They are riverboat gamblers dressed in Armani. They are playing with company money, corporate assets. Their cell phones burn hotter than a California brush fire.

Some are craftier than others. Some are more aggressive than others. Some go for the big payoff—risk takers supreme. Others are content to settle for the smaller, safer bet.

Here’s an example.

It’s around Valentine’s Day (ironically) in 1989. The Pistons’ wheeler and dealer has been burning up the phone lines. He has a mercurial, tempestuous, volatile player on his hands. The player cannot any longer get along with his coach. That comes from the player himself.

The riverboat gambler tries to broker a meeting between player and coach. The player rebuffs the efforts.

“I told Adrian, ‘Coach Daly will talk to you anytime you want.’ But Adrian didn’t want to talk.”

The speaker was Jack McCloskey. And he was recalling the circumstances surrounding his gutsiest trade ever. That’s my opinion and I am sticking to it.

McCloskey traded Adrian Dantley to Dallas for Mark Aguirre, straight up. Dantley—as McCloskey recounted to me via phone several years ago—was an unhappy camper in early 1989, despite the Pistons tearing up the league, seeking that elusive championship. And frankly, the Pistons weren’t too pleased with Adrian.

The Pistons made the Finals in 1988, but lost in seven hellacious games to the Lakers. They had come close—oh, so close—to winning their first title in franchise history.

There had been grumblings that Dantley, perhaps the best post-up small forward in league history, was a ball and chain around the Pistons’ offense. The term black hole was even used—as in when the basketball was delivered to Dantley, it was never to be seen by a teammate again.

The Pistons had some athletes who could get up and down the floor, led by the smiling assassin Isiah Thomas. But when Dantley got the ball—usually on the wing—the offense came to a screeching halt. After two-plus seasons of this, certain folks got annoyed. Certain folks in very high places.

So it was that even with the backdrop of a team playing .750 basketball, Dantley was frustrated. He felt the tension, and he (rightly) felt that it was directed toward him.

McCloskey pleaded with Dantley to talk to his coach, Chuck Daly. Dantley refused.

“I had no choice,” McCloskey told me that evening in 2009. “I had to trade Adrian.”

The trade deadline was coming up. And even if McCloskey—so aptly nicknamed “Trader Jack”—felt that he “had no choice” but to trade Dantley, I still say it was his gutsiest trade. Maybe the gutsiest in Detroit sports history.

The trade, for another player who had issues with his coach—Aguirre—could have had a negative affect on team chemistry. For despite Dantley’s foibles, the Pistons were used to them. And they knew the reputation that Aguirre had in Dallas and his Reggie Jackson-Billy Martin relationship with coach Dick Motta, who himself would never win Mr. Congeniality. With Dantley vs. Aguirre, it was kind of like the devil you know versus the one you don’t.

McCloskey made the trade. Dantley, who to this day thinks the deal was engineered by Thomas (Aguirre’s close friend), brooded. Aguirre was taken to dinner by a contingent of Pistons and the law was laid down. The Pistons won their championship four months later. But it could have gone oh so wrong.

Dave Dombrowski, the Tigers’ riverboat gambler of today, emerged after Tuesday night’s game, beaming. He headed for manager Jim Leyland’s office as the media in the clubhouse murmured. It was less than 24 hours before Wednesday’s non-waiver trade deadline.

Moments later, Dombrowski spoke to the press and revealed why he had the look of a man who had just beaten the house.

Sometime during Tuesday’s game, Dombrowski was burning up his phone line, talking trade with the Boston Red Sox fellow AL first place tenants.

The Tigers, concerned about the fate of shortstop Jhonny Peralta’s status (his connections with the Biogenesis lab may result in a 50-game suspension), decided that they had no viable options internally for Jhonny should MLB remove him via suspension.

So Dombrowski, wearing his Armani suit and pink tie, playing at the table with the boss’ assets—namely, minor league prospects—worked out a three-way deal with Boston and the Chicago White Sox.

Boston would get outfielder Avisial Garcia, who the Tigers are very high on, and sometimes big league reliever Brayan Villarreal. The Red Sox would then ship Garcia to the White Sox for starting pitcher Jake Peavy.

And the Tigers were getting shortstop Jose Iglesias from Boston, whose glove has been compared to Ozzie Smith and Omar Vizquel’s, no less.

Dombrowski was beaming because he not only patched up shortstop for this season, should Peralta be suspended, but he covered the position for years to come. Iglesias is 23 years old and isn’t eligible for free agency until 2019, which to me still looks like a year out of an H.G. Wells novel.

Dombrowski is the ultimate poker player. Earlier that day, he solemnly told the press that, after his Monday trade for reliever Jose Veras, the Tigers were likely done trading. That Peralta’s status wasn’t dire enough to create urgency for another deal before 4:00 p.m. Wednesday afternoon.

He said these things even after he had been in talks with the Red Sox that morning.

A good gambler never shows his cards until it’s time.

We have seen the best and worst of general managers in Detroit.

We have seen Russ Thomas, who was a tightwad and a curmudgeon straight out of a Dickens novel, holding onto Lions owner Bill Ford’s money like it was his own.

We have seen Ned Harkness, whose personal grudges and misplaced college attitude destroyed the Red Wings for a decade and a half.

We have seen Matt Millen, and that’s all that needs to be said here.

But we have also seen Jimmy Devellano, whose moves didn’t always work with the Red Wings, but no one could accuse Jimmy D of being passive or uncreative.

We have seen the aforementioned McCloskey, who took a 16-win team and in less than five years, had them competing seriously in the NBA playoffs, eventually winning two championships in a row in 1989-90.

We now see Kenny Holland, who proved that his hockey GM chops weren’t propped up by owner Mike Ilitch’s pocketbook. After the NHL instituted a hard salary cap in 2005, Holland continued to show why he is among the best in the business, even when not able to work with a blank check.

And the Tigers have Dombrowski, who is as good as they come in baseball. His moves don’t always work, either, but they do most of the time and he is another that no one can accuse of being passive. He knows the clock is ticking on his octogenarian owner, who wants a World Series title so badly he can taste it.

Did Dombrowski’s cat-who-swallowed-the-canary smile on Tuesday night say it all?

We’ll find out in about two-and-a-half months, won’t we?

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