San Diego Chargers General Manager A.J. Smith is known for being a tough executive to negotiate with over player contracts. The team has spent years drafting well, using those players through the early years of their careers, then drafting their replacements and letting those mid-to-late career guys go on to other teams.

When Drew Brees’ deal was up, the Chargers let him go to New Orleans and promoted Philip Rivers. LaDainian Tomlinson was the face of the franchise for nine years. But as his value fell even he was shown the door. That’s just two examples.

It’s led to a number of tense situations. Linebacker Shawne Merriman has had a couple of verbal sparring sessions with Smith and, likely, he will be one of the next big-name players to find a new home soon — he very likely would have already if the collective bargaining agreement’s pending end hadn’t converted a couple hundred players from unrestricted free agents to restricted free agents last offseason.

But Smith is playing with fire with two players on his current roster, holdouts Marcus McNeill and Vincent Jackson.

McNeill, a solid left tackle, says he wants to stay in San Diego, but not playing under the tender offer the Chargers offered during the offseason. He’s holding out, training in Florida while his agent tries to work out a deal. His situation has played out much more quietly and behind-the-scenes than that of Jackson, a young, talented-but-sometimes-troubled wide receiver who has been pushing the team to trade him.

Jackson has other issues. He’s suspended three games for an offseason DWI. With his holdout, the Chargers put Jackson — and McNeill — on the roster exempt list, meaning they will have to sit out three more games once they do report.

But the league gave Jackson a reprieve. If the Chargers traded him by Wednesday, Jackson would only have to miss a total of four games. His agents shopped him and supposedly had a couple deals in place, including one from Minnesota that supposedly would have brought San Diego a second round pick in 2011 and a conditional pick in return for Jackson, depending on whether or not the Vikings signed him to a long-term deal.

Smith said no. Instead, assuming Jackson sticks to his guns and refuses to re-sign with San Diego, the Chargers will get a 3rd round compensatory pick when he leaves … in the 2012 draft.

Now, I can see to some extent why Smith wanted to make a point with Jackson in the first place. The receiver has, at times, been his own worst enemy. He’s been perceived as a prima donna at times through these negotiations and his off-field issues — he’s one strike away from a year-long suspension — have reduced his leverage.

But if in fact this offer was on the table, Smith is playing a bit of Russian Roulette with Jackson’s career — and his own. It’s risky enough turning down what would have been an improved draft pick a year sooner — a deal that would have allowed San Diego to wash their hands of a talented-but-inconsistent performer who is almost certainly going to leave anyway.

But I think that is less the issue than what other players will see in Smith’s stance when they consider San Diego as an option during their own free agency negotiations.

Jackson’s agents, Neil Schwartz and Jonathan Feinsod, have both been quoted saying there were deals in place but that the Chargers’ demands were unreasonable. They represent other players. Players talk. Word that the general manager of the Chargers had a chance to make a deal but didn’t, apparently out of spite and the desire to make a statement, will get around.

What is the upside for Smith in further angering Jackson? He could have traded him to an NFC team, ensuring that — at most — Jackson would play San Diego only once every four years unless the two teams met in the Super Bowl. What is the upside in turning down better draft position and multiple picks and holding out for a likely third rounder a year later? What is the upside in risking making San Diego a destination NFL players want to avoid?

San Diego under Smith has been very successful, at least in the regular season, at drafting and replacing, drafting and replacing. They better hope that trend continues. Otherwise, in sending the “don’t mess with A.J” message, Smith may have overplayed his hand in this case.