"We've encouraged him to test the market' - When Brian Cashman angered Derek Jeter with one particular remark during contract negotiations

Derek Jeter never played for a single other team in his MLB career. The thought of a franchise icon (one of the best in a storied history of great players) playing elsewhere probably makes his fans shudder, but there was a time when that was almost the case.

Jeter was a free agent multiple times throughout his career, but he never left the team he was drafted to. He remained a life player even though the relationship between he and his GM fractured.

At one point during negotiations, Brian Cashman outright implored Jeter to hit the open market. According to Bleacher Report, he said:

"We understand his contributions to the franchise and our offer has taken them into account. We've encouraged him to test the market and see if there's something he would prefer other than this. If he can, fine. That's the way it works."

The New York Yankees GM had grown tired of negotiating with no end, so he asked Jeter to see what other teams might give him in an effort to justify what he'd offered him.

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Derek Jeter never left the Yankees

Derek Jeter ultimately came back to the table with Cashman, but he was upset with how public the negotiations went. The five-time World Series champion felt a little disrespected.

According to ESPN, Jeter got up to leave the discussions, but Cashman asked the shortstop to stay and hear him out:

"You said all you wanted was what was fair. How much higher do we have to be than the highest offer for it to be fair?"

Ultimately, he signed a three-year deal for $51 million (not much compared to today's mega contract standards) to remain with the New York Yankees. He would remain with his franchise until he retired, but it was more than risky at a certain point.

Derek Jeter never left the Yankees

He would go on to make the Hall of Fame and has become one of the most iconic Yankees of all time, but it would have been interesting to see what the perception would have been had he left at any time.