When was the last time you were upset about the Cowboys losing a player to free agency?

I’m not going to lie, this one is going to sting a bit.

Of all the conversations going on about their own free agents, the front office of the Dallas Cowboys has been rather quiet when it comes to Byron Jones. It’s been highly speculated that the veteran cornerback could be left on the outs this offseason as the team prepares to deal with the contracts of Dak Prescott and Amari Cooper. Mum has been the word when it comes to Jones, and when words are said, they certainly aren’t very reassuring.

It’s not easy to let first-round draft picks leave. It’s even harder when that player has earned All-Pro honors. And it’s even more difficult when that player plays at one of the more important positions in the league. Add in the fact that he’s a gold-star high-character guy who just so happens to be the Cowboys designated player rep for the collective bargaining agreement that is in the works right now, and it just seems like all the boxes are checked for Jones to stick around.

But apparently, they’re not as the business of the NFL is rearing its ugly head. Based on the tea leaves, the Cowboys don’t value Jones as much as what he’s likely to earn on the open market. Financially, it’s going to be great for Jones as opportunities like this aren’t always readily available since the shelf life of a pro football player isn’t very long. It’s sad for fans that have grown attached to him, but these kind of things happen. It got us thinking, when was the last time you’ve really felt upset about a Cowboys player leaving in free agency?

For this exercise, remember - we are just talking about free agents with expiring contracts. The Emmitt Smith to Arizona situation doesn’t count because he was released. Same goes with DeMarcus Ware, Tony Romo, and all others who were cap casualties.

Not that we got that out of the way, who do you got?

DeMarco Murray (2015)

Nobody much talks about it these days, but man were there some upset Cowboys fans when the All-Pro running back left in free agency. Maybe it was because he had just come off a Cowboys franchise record, 1,845-yard season. Or maybe it was because he left Dallas to go play for the rival Philadelphia Eagles. Regardless, the Cowboys front office was never close to retaining him as they just didn’t think it was worth the investment. And you really couldn’t blame Murray for signing a nice five-year, $40 million deal with the Eagles.

Ultimately, the Cowboys made the right choice as Murray only played three more seasons after leaving Dallas. He only got half of what his contract offered. In the words of Stephen Jones, he had a great run...and here it is:

Ken Norton Jr. (1994)

Back in 1994, the salary cap was first instituted, which was horrible timing if you’re a team putting together a dynasty. The Cowboys were coming off back-to-back Super Bowls and had a plethora of talent, but they were on the verge of taking a hit as several players entered free agency. The first big blow that year was losing Ken Norton Jr..

Norton Jr. was selected in the second round of the 1988 NFL Draft, one round after Hall of Fame receiver Michael Irvin. It was the last draft under the reign of Tom Landry as Jerry Jones and Jimmy Johnson would both arrive the following year. Norton was coming off a career year where he tallied 159 tackles. It was bad enough that he left Dallas, but to go play for the one team that was challenging the Cowboys that decade, the San Francisco 49ers, was just outright yucky! How could he? Norton helped his new team dethrone the Cowboys that year, breaking up a possible four-peat for Dallas, and giving him three straight Super Bowl victories instead.

Over the past five years, Norton has been a defensive coordinator, with the last two being with Seattle. He took over the job vacated by Kris Richard. We still appreciate all that he gave the Cowboys as he sure was a big-time playmaker in Super Bowl XXVII.

Your favorite no. 2 wideout

Over the years, the Cowboys have seen some good receivers leave for bigger paydays. Alvin Harper had a career season in 1994 with 821 yards and eight touchdowns, but he did next to nothing after signing a nice contract with the Tampa Bay Buccaneers.

Laurent Robinson was another one many thought the Cowboys let slip through the free agent cracks after recording a career-high 858 yards and 11 touchdowns in 2011. As it turned out, he was just a benefactor of Tony Romo and the Cowboys system as his career then went to Jacksonville to die.

And then there is Cole Beasley, who left last season. He actually fared well in Buffalo, putting up similar yards as he did last year with Dallas; however, he found the end zone six times with the Bills, a new career high for him. We miss having a little sauce around, but we’ll always have spirit fingers.

Which free agent were you most disappointed when he signed with a different team?