Yankees: How to extend their championship window

The rationale behind these extensions is you pay a player more upfront in order to buy out an extra year or two of free agency. These deals often end up as some of the best value deals in baseball, greatly benefitting the team.

In the Yankees case, extensions like these can help them extend their championship window a couple of years by locking up their core players at bargain prices before they significantly decline.

The Yankees would also have to decide who to offer these extensions too, which is a difficult question in its own right. I would first look towards Torres and Andujar, using Scott Kingery’s extension with the Phillies as a starting point.

While Andujar will have some time to prove himself in the majors before any extension is reached, he is also not as highly ranked on prospect lists such as Kingery. On the other hand, Torres is more highly rated than Kingery but similarly will have little to no MLB experience before his extension.

An extension like Kingery’s has the most potential to provide surplus value, although with more risk since he hasn’t proven anything yet at the big-league level. His six-year deal covers all of his arbitration years and includes an additional three club options valued at $13 million, $14 million, and $15 million apiece during the hypothetical prime of Kingery’s career.

If Kingery lives up to his hype, this deal is a huge bargain compared to what he could command on the free agent market. Given the Yankees financial might, they could withstand any backfired extension if the player doesn’t live up to his billing, limiting the riskiness of such a deal.

It would be wise for the Yankees to act now with Torres and Andujar extensions to maximize their leverage and capitalize on the momentum of similar extensions being made this year.

Kingery’s deal was a nightmare for the MLB player’s union because it was one of the first extensions that included three additional years of control for the team, and it also followed a tumultuous offseason where player salaries declined for the first time since 2004.

There is bound to be pressure from the players union dissuading players from accepting extensions like these and capping their potential earnings, so the Yankees need to strike now while the iron’s still hot.