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Over the course of his two decades in the major leagues, Derek Jeter was the most thoughtful person in baseball.

Never any particular intellectual, Jeter was instead a master of rhetorical prudence. He said the right thing at the right moment in just the right sort of way. Since he was always available and authoritative, he became MLB's de facto spokesperson. If you wanted to take the pulse of the game, the heart of it was beating within a tight radius of Jeter's locker.

When his performance level dipped during his final few seasons, Jeter's reputation as the ur-baseball pro made him immune to criticism. Since he'd decided playing like an anvil wedged into the ground at shortstop was the right way to go out, everyone else accepted that, too.

When he finally left the game, he did so like a Roman general on a season-long triumphal march around the league. Everyone agreed that we would not see his kind again.

It took Jeter 20 years to build up that reputation for good sense and proper comportment, and just a few weeks to tear it down.

Since taking over as minority owner and chief executive of the Miami Marlins, Jeter has fronted a series of decisions that amount to surrendering before the opposing army has been told the war is on.

He is not dismantling a team or rebuilding a team. He's destroying one so that it can become the pro-sports equivalent of a benefits cheat – surviving handsomely on TV money and equalization handouts from better clubs, while making no effort to find gainful employment as a contender.

"We've seen one of our major-league jewellery stores become a pawn shop," super-agent Scott Boras said this week.

Jeter didn't buy the Marlins this past summer. Instead, he traded that hard-won reputation for a small piece (4 per cent) of the team and a job he is not qualified to do.

At that point, the new owners must have already known what they wanted – to chop the club up and sell it for parts. Jeter was brought in to give their fire sale the gloss of competence. It rubbed off quickly.

The frenzy began around National League MVP Giancarlo Stanton, who is owed $295-million (U.S.) over the next 11 years. Everyone and his baseball-agnostic brother knew the Marlins wanted rid of that debt.

Despite his cost, Stanton still represented value, because he has only just turned 28 years old.

This is where a competent organization would have begun the judo stage of negotiations – taking the pressure felt by a team to rid themselves of an ugly storyline and shifting it onto the player, who wants more than anything to feel settled again. Time is on the team's side. Jeter frittered that advantage away.

Within weeks, he traded Stanton to the St. Louis Cardinals. Stanton, who had a full no-trade clause, refused to go. Nearly immediately after that disappointment, Jeter dealt him to the wretched San Francisco Giants. Stanton refused again.

Jeter reportedly threatened to keep Stanton and make him a Marlin for life (what a ringing endorsement of the club by its new boss – "Welcome to hell!"). Stanton said, "Fine."

And so Jeter lost.

Stanton was traded to the New York Yankees, essentially for nothing.

The return was bad enough. The faint whiff of collusion between Jeter and his old club was worse.

The bumbling manner in which l'affaire Stanton was handled might have given a smarter team pause. Maybe it was time to hang back for a few weeks, lie very still on the ground and pretend to be alive.

But, apparently, that's no longer the Jeter way. After 20 years of calm, what little remains of his hair is suddenly on fire. He'd already traded all-star second baseman Dee Gordon. Hours after the Stanton trade was made official, Jeter dealt his best young player, outfielder Marcell Ozuna, to the Cardinals.

The Stanton trade was a salary dump. As such, it was at least logically coherent. The Ozuna trade was a … well, it's difficult to see what the point of it was. Ozuna is young, cheap, under team control for two more seasons and about to become one of the best players in baseball. It does not require a deep dive into BABIP or wRC+ to figure out that those are the sorts of guys you would rather keep.

Jeter's Marlins were no longer just trying to save money right now, or a couple of years from now. They were now trying to save money forever.

Jeter compounded the error (reductive math is becoming his only talent) by skipping the first day of baseball's winter meetings – a chance to explain himself – and attending a Miami Dolphins game instead. The message was clear – "Here I am, out amongst the peasants, not caring what they think." The old, baseball-playing Jeter would've gotten the benefit of the doubt. The new, baseball-managing Jeter is getting none.

A couple of months on the job and he is already a pariah in Miami, booed in public. Given the time frame and scale, it may be the most ambitious reputational self-destruction in sports history. Jeter's hardly the first former pro to prove a bust at running a team. Many of the virtues of great players – heedless aggression, a selective deafness to criticism, single-minded commitment to mission – are executive sins.

But Jeter's ruinous path thus far is something more than an inability to adapt. He's doing as an owner what he would never have considered as a player – embracing failure.

In return for an important sounding job title that flatters an ego that we didn't realize up until now he had, Jeter has allowed himself to become a shill.

However disappointing it is to the average Marlins baseball fan, it is even moreso to baseball in general.

Derek Jeter was emblematic of what the game stood for – hard graft, honest effort, pride in accomplishment. Now, he's pawned that off, for a brass nameplate and a seat at the Big Boy table.

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