On Monday afternoon, the Washington Nationals agreed to terms with free-agent ace and reigning World Series MVP Stephen Strasburg on a record-breaking seven-year deal worth $245 million. Strasburg's contract represented both the richest ever signed by a pitcher (though a third of the pact will reportedly be deferred), and the one with the highest average annual value. On Tuesday night, Gerrit Cole shattered that mark, reportedly agreeing to a nine-year deal worth $324 million to join the New York Yankees.

Cole's agreement comes after weeks connecting him to the Yankees, Los Angeles Dodgers and Los Angeles Angels, among others.

This, then, is the winter of record-breaking pitcher contracts. It's worth noting that Strasburg and now Cole are just the fifth and sixth pitchers to ever top $200 million. Prior to Strasburg's deal, the only pitchers to top so much as $190 million were David Price (who held the record, at $217 million), Clayton Kershaw, Max Scherzer and Zack Greinke. Cole, obviously, is the first to ever go over the $300 million mark.

For more perspective, here are the 10 richest pitcher contracts in history, as judged by total value (salary information courtesy of Cot's Contracts, which is hosted at Baseball Prospectus):

RankPitcherTeamAmountBeginsEnds
1.Gerrit ColeYankees$324M
20202028
2.

Stephen Strasburg

Nationals

$245M

2020

2026

3.

David Price

Red Sox

$217M

2016

2022

4.

Clayton Kershaw

Dodgers

$215M

2014

2020

5.

Max Scherzer

Nationals

$210M

2015

2021

6.

Zack Greinke

Diamondbacks

$206.5M

2016

2021

7.

Justin Verlander

Tigers

$180M

2013

2019

8.

Felix Hernandez

Mariners

$175M

2013

2019

9.

CC Sabathia

Yankees

$161M

2009

2015

T-10.Masahiro TanakaYankees$155M20142020
T-10.Jon LesterCubs$155M20152020

And here are the 10 most lucrative pitching contracts, according to average annual value:

  1. Gerrit Cole, $36 million
  2. Stephen Strasburg, $35 million
  3. Justin Verlander, $33 million
  4. Zack Greinke, $32.5 million
  5. David Price, $31 million
  6. Clayton Kershaw, $31 million
  7. Max Scherzer, $30 million
  8. Roger Clemens, $28 million
  9. Jacob deGrom, $27.5 million
  10. Jon Lester, $25.8 million

Cole's AAV is also the highest in baseball, eclipsing Mike Trout, who previously held that distinction at $35.5 million. It's the fourth-largest deal in baseball history overall