Will the stalemate between the Yankees and Derek Jeter ever end? After a five hour meeting Wednesday afternoon in Tampa, the Yankees and the Jeter camp have not come close to agreeing to new contract. Talks were apparently ‘good’ on Wednesday, but no deal was signed. The Yankees are prepared to increase their offer, but could that push things over the edge? At this point, the only thing that could be considered ‘good’ would be a Yankee press conference where they ‘re-introduce’ Derek Jeter to New York City. But I still think we are very far from that point. The fact still apply; the Yankees are sticking with their initial offer of 3 years, $45 million. The Jeter camp wants a 4-6 year deal worth presumably $20-$25 million per season. With Alex Rodriguez, Mark Teixeira, and CC Sabathia set to make mega bucks with the Yankees for the foreseeable future, could the Captain ultimately be too hurt to accept less and return to the Bronx?

History shows us that sometimes, teams will let go of their iconic players if they simply do not fit into the team’s long-term picture. The Giants let go of Willie Mays. Jackie Robinson and the Dodgers went their seperate ways. The same goes for Joe Montana and the 49ers. However, economic times are clearly different now than they were when these players played, plus the Yankees aren’t exactly strapped for cash.  That’s what makes the Jeter situation so puzzling and even more frustrating for Derek himself.

Derek Jeter is one of the few remaining Yankee legends. His post-season success and overall demeaner does not come around very often. However, the skeptics will choose to break out the spreadsheets and devalue his importance to the Yankees. They could sit here and kill Jeter all day with sabermetrics and silly statisical analysis, but the facts remain that he IS the face of the Yankees. Clutchness and compassion cannot be measured. You won’t find that anywhere on a spreadsheet.

Baseball fans know that Derek Jeter has way too much pride to voice his frustrations to the media. Derek Jeter has never taken that route and never will. Instead of drinking the so-called ‘Reality Potion’, he choose to endulge himself on something much more tasty, something called ‘Self-Respect and Class’. It feels pretty good, too.

At the end of the day, the Yankees will ultimately do what’s best for the team. Business is business. However, is a few million dollars and an extra year really going to hurt the Yankee brand? If they are willing to play this type of hardball with their Captain, what type of message does this send other Yankees? Don’t get old?

Derek Jeter will ultimately decide to what’s best for himself and for his family. The biggest offer will come from the Yankees, but will too much damaged have already been done?

At the end of the day, the Yankees need to ask themselves what will hurt more.

Their checking account having a few million dollars less or the disappointment on the faces of Yankee fans if he does not return to the Bronx in 2011.

The sooner the deal gets done, the easier it will be to let go of hurt feelings.