Ten players who deserve contract extensions, with suggested figures

Bryce Harper and Manny Machado are two players who deserve long-term contract extensions. Getty Images

As we've seen again this offseason, free agency is still a very viable route for a player to reel in a favorable contract, whether it's the $70 million deal Ian Kennedy agreed to with the Royals or Chris Davis' $161 million deal with the Orioles. Arbitration settlement rates are also at an all-time high, and many teams seem to have plenty of cash to spend. With a long history of salary trends going in one direction, the only way teams can stay ahead of the curve and get an actual "bargain signing" (relatively speaking) is to sign their best young players to long-term contracts before they ever reach arbitration, let alone free agency. The further away they are, the more risk the team assumes, but the cheaper they can usually get the player.

In general, GMs prefer to observe their young players at the big league level for three years before giving them a long-term contract, but by then it's often too late to lock in the player at a good yearly rate. Therefore, in recent years, teams have begun signing them after just one or two years, primarily the elite position players.

I'm in favor of the signing-them-early strategy, but not pitchers. I wouldn't want to sign them to a long-term deal until they're a year away from free agency. Why? Because they're at a much higher risk than position players of breaking down and missing full seasons, and the club is stuck paying the elevated salary. There are exceptions, of course, like Clayton Kershaw and Madison Bumgarner, but I'd try to limit it to left-handers who are clear staff aces at a young age.

Meanwhile, there are several players who deserve to be extended, like Josh Donaldson and Todd Frazier, but the issue in their cases is they have already proved their worth and consistency, so good luck getting them at a bargain rate. It's worth the effort to try; in some cases, you can at least move their free agency back a few years.

But there is a certain subset of players who deserve long-term contracts, and the 10 players below fit firmly within it. Their teams should -- and perhaps will -- attempt to extend them between now and Opening Day this year. You'll note they all fit my criteria: a left-handed ace or position player with three years or less of service time and at least three years away from free agency.

I examined 22 recent contracts (all since 2013), from Miguel Cabrera's to Mike Trout's to the ones signed this offseason, that best represent the current marketplace and can be used as a basis to project the value of the players below if they were to sign long-term contracts now. Keep in mind that inflation, years of service time, arbitration eligibility, free-agent years, statistics, trends, future projections, makeup and character, as well as which agency represents the players, all must be factored in when determining the value of these players.

Bryce HarperBryce Harper, OF, Washington Nationals
2015 WAR: 9.9 | Service time: 3.159 (three years, 159 days)
Arbitration-eligible: 2017 | Hits free agency: 2018

Harper, 23, was the best player in baseball last year, and now he's just three years away from free agency. He's represented by power agent Scott Boras, and when it comes to star players, the Boras Corporation is the most difficult agency to do a contract extension with prior to free agency. To make matters worse, the 2018 MLB winter meetings will be held in Las Vegas, where Harper grew up (as a New York Yankees fan). It just so happens that the Yankees have a few big contracts coming off the books before then: Alex Rodriguez, CC Sabathia, Mark Teixeira, Carlos Beltran, Brian McCann, Brett Gardner, Chase Headley and really everyone else not named Masahiro Tanaka or Jacoby Ellsbury.

If the Nationals have any hope of signing Harper long-term and keeping him a National for life, it probably must happen this spring. They'd also have to be willing to make him the highest-paid player in baseball history, with the longest term and highest dollar amount we've ever seen; if they're not willing to, they might as well not even call Boras. What would it take to sign him? Well, if you're thinking something close to Giancarlo Stanton's $325 million deal, you're not even close -- the number would have to begin with a 4.

Would the Nats pay it? Well, it's worth noting they do have a history of spending big money on players they want, including Max Scherzer ($210 million) and Jayson Werth ($126 million).

Projected contract: 14 years for $407 million (average annual value: $29-plus million). Boras usually takes his guys to free agency, but perhaps a record-breaking contract will pique his interest. Harper would become the first $400 million player, and let me say this (while you're picking up your jaw from the floor): I went conservative here. If he were to actually reach free agency, I think he not only surpasses this projection, but he shatters it. Gulp.