Rougned Odor signed a six-year extension before the 2017 season.

Now the Rangers are looking to do the same with Joey Gallo and Nomar Mazara. They drafted and developed both players, and want them to be Rangers for life. Both Gallo and Mazara are interested as well. They said they have been a Ranger from the beginning and want to be a Ranger for life.

Usually when you have both sides interested, it happens. Until agents get involved.

It’s a smart move for both sides, with risk for both sides.

For the player, they get the financial security at a young age. In return for delaying their free agency, they theoretically earn more than they would have won during arbitration those years. And, they have protection in case they are injured or in case their performance falls off the face of the earth, as did Odor’s in 2017. But they are postponing their free agency to when they hit the market at an older age, which we have seen the last few years is not as desirable.

The player gets peace of mind. But also that nagging feeling that they are leaving a lot of money on the table.

For the team, it gains cost certainty on its payroll, and it locks up good young talent for longer than the six years it would normally control him until he hits free agency. The risk is that the player never takes those steps forward and the team is stuck with a big contract for little performance. The Rangers faced that dilemma after Odor’s 2017, and to some extent with Elvis Andus after his development stalled once he signed a long-term deal. What if the player isn’t motivated to improve since he is now set for life?

Evan Longoria signed one of the more team-favorable extensions early in his career with the Tampa Bay Rays. After five big league seasons in which he won a Rookie of the Year award, played in three All-Star games and finished in the top twenty of MVP voting four times, Longoria signed a ten-year $100 million contract one year before he was eligible to be a free agent.

Yes, he could probably have gotten more in the open market had he waited a year, then pursued free agency, but he wanted the security, and he wanted to be a Ray for life.

It was a sweetheart deal for Tampa Bay. They got an elite-level young third baseman at a bargain of what his market value would have been. It was a win-win for both, but much more for the team. It’s interesting to note that Longoria never made another All-Star team after that.

On the other side of the extension coin was the case of Houston’s Jon Singleton, a can’t miss prospect the Astros locked up early. Before he even saw his first major league pitch, Singleton was going to be a star, the Houston Astros predicted. Forgoing paying him the major league minimum and anticipating they would be having to pay him countless millions in arbitration in three seasons, the Astros made the bold move of giving Singleton a $10-million, five-year contract before his rookie season. Singleton jumped at the chance to sign it. It angered the union, who felt Singleton was short-sightedly leaving money on the table. But Singleton was set for life. A life he then proceeded to squander.

For their ten million dollars, the Astros got 114 games out of Singleton in two seasons, fourteen home runs, and a batting average of .171. And three positive drug tests.

It was a deal that ended up being a disaster for the team and a godsend for the player.

Now Gallo and Mazara and the Rangers are at the same crossroads. To extend or not to extend? That is the question.

But the real questions are: Do they do it now or next off-season? What if they have bad years? What if they have great years? What if they never learn to beat the shift? What if they lean discipline on that two-strike approach? What if they take that new step? What if they don’t? What if I could get more in the open market? What if we are paying them more than they can get in the open market?

What if? What if? What if?