Coming into the offseason, the question was not whether right-handed free agent Gerrit Cole would sign the largest pitching contract in baseball history, but rather how much larger than the current record would it be? David Price held the total guarantee record at $217 million and Zack Greinke the average annual value record at $34.42 million. Cole beating both marks was fait accompli.

Now that the Winter Meetings have begun, it seems possible Cole will become the first $300 million pitcher in baseball history. He is poised to obliterate Price's total guarantee record and move the average annual salary bar up quite a bit as well. Here are four reasons Cole has a chance to become baseball's first $300 million hurler.

1. Strasburg has already raised the bar

Monday afternoon the Nationals and World Series hero Stephen Strasburg agreed to a new seven-year contract worth $245 million. The deal reportedly includes $80 million in deferrals. Strasburg now holds the pitcher records for total guarantee and average annual value ($35 million), but only until Cole signs. Three things to consider:

  • Cole is 26 months younger than Strasburg.
  • Strasburg's injury history is much uglier.
  • As good as Strasburg is, Cole is better.

Over the last two years Cole pitched to a 2.68 ERA with a 37.3 percent strikeout rate in 412 2/3 innings. Strasburg had a 3.48 ERA and a 29.8 percent strikeout rate in 339 innings during the same period, and remember, he was in the non-DH league. Cole has been the objectively better pitcher and his age and health make it reasonable to believe he'll be the better pitcher going forward.

Now that the 31-year-old Strasburg has signed a seven-year deal with his injury history, it's not hard to envision the 29-year-old Cole getting eight guaranteed years. Nine years might even be within reach, though I think that's unlikely. Eight years and $36 million per year is $288 million total. Would a team really consider an extra $12 million a dealbreaker? Point is, Cole is no longer chasing Price and Greinke for the contract records. Strasburg moved the goalposts.

2. He's still in his prime

Cole turned only 29 in September. He's going to play nearly the entire 2020 season at that age and it won't be until spring training 2022 that he will be as old as Strasburg is now. Whichever team signs Cole is getting a pitcher who is right smack in the middle of the best years of his career, not someone who may have peaked already and is about to begin his decline. Teams will pay for prime seasons and prime seasons are what Cole is offering. That will undoubtedly raise the asking price.

3. He's arguably the best pitcher in baseball

Although he did not win the Cy Young, Cole led MLB in FanGraphs WAR this past season as well as the American League in ERA, and his 39.9 percent strikeout rate was the highest in history among qualified starters. The Steamer projection system also expects Cole to lead MLB pitchers in WAR again next season:

  1. Gerrit Cole: 6.3 WAR
  2. Jacob deGrom: 6.1 WAR
  3. Max Scherzer: 5.9 WAR
  4. Justin Verlander: 5.3 WAR
  5. Chris Sale: 4.9 WAR 

Projections are not predictions. They are an estimate of talent level, and the objective projection system considers Cole the most talented pitcher in the game. The Astros helped Cole improve through pitch selection -- most notably, they got him to stop pitching to contact with sinking two-seamers and emphasized elevated four-seamers -- and that's something that can travel. 

There is every reason to believe Cole will remain on the very short list of the game's best pitchers going forward. The stuff is there, the execution is there, and the pedigree is there. Everything about Cole points to a no-doubt ace on the right side of 30. Teams will pay for that. 

4. The right teams are interested (and desperate)

This is perhaps the single biggest reason Cole has a chance at $300 million. The deep-pocketed Yankees are involved -- the YES Network's Jack Curry reports the Yankees will make a "very, very competitive offer" soon -- and Cole is their white whale. They drafted him in the first round in 2008 and tried to acquire him from the Pirates two years ago. The Yankees aren't going to lose out on Cole a third time without putting their best foot forward.

The Angels, the other team most connected to Cole, are desperation personified. Three postseason games during the Mike Trout era, all losses, and one postseason series win since 2005. GM Billy Eppler is entering a lame duck season and the club has built a who's who of coaching staffs this winter. Joe Maddon as manager, Mickey Callaway as pitching coach, so on and so forth. The Angels are desperate for pitching and Cole, an Orange County native, is an obvious fit.

The Dodgers have been less involved in the Cole sweepstakes compared to the Angels and Yankees but they are involved to some degree. The Phillies as well, though the recent Zack Wheeler signing presumably takes some of the pressure off. Bottom line, Cole has some very ultra-wealthy teams chasing after him, and there's desperation in play too. The Angels are clearly desperate. The Yankees and the Dodgers may be to a lesser extent.