At some point soon, possibly even during the Winter Meetings this week, Gerrit Cole will sign the largest pitching contract in baseball history. It might even exceed $300 million. Stephen Strasburg signed a seven-year, $245 million deal with the Nationals on Monday and Cole is two years younger, has a cleaner injury history, and has been the better pitcher the last two years.

The New York Yankees are among the primary suitors for Cole -- I think it's fair to call them the favorites to sign him right now given their financial might and more obvious path to contention than the Angels -- and, according to the New York's Post Joel Sherman, the Yankees are shopping lefty J.A. Happ in an effort to clear payroll space to sign Cole. From Sherman:

As a way to potentially fit Gerrit Cole more comfortably into their payroll — specifically for luxury-tax purposes — the Yankees continue to shop J.A. Happ, as The Post first reported last month.

Two executives from outside teams described the Yankees as actively looking to trade Happ.

Happ, 37, is owed $17 million next season with a $17 option for 2021 that will vest with 27 starts or 165 innings in 2020. He made 30 starts and threw 161 1/3 innings this past season and posted a 4.91 ERA with 34 home runs allowed. Happ could rebound next year if MLB un-juices the baseball, though his velocity has slipped with age.

Salary dumping Happ would likely require the Yankees to attach a sweetener. Two years ago they gave the Padres young righty Bryan Mitchell to take on Chase Headley's $13 million salary, so New York has done something like this before. The club's rotation depth chart currently lines up like this:

  1. RHP Luis Severino (missed most of 2019 with shoulder and late injuries)
  2. LHP James Paxton
  3. RHP Masahiro Tanaka
  4. RHP Domingo German (awaiting suspension under MLB's domestic violence policy)
  5. LHP J.A. Happ
  6. Jordan Montgomery (missed most of 2019 with Tommy John surgery)
  7. Jonathan Loaisiga

Add Cole and subtract Happ, and the Yankees could either roll with Montgomery or Loaisiga until German returns, or sign a lower-cost free agent to be their fifth starter. Giving away pitching depth is rarely a good idea. In this case, the Yankees may have no choice but to unload Happ in order to sign Cole without blowing through MLB's third luxury tax tier at $248 million.

Last offseason the Angels and Phillies were among the teams that pursued Happ and both clubs could have interest in him again this offseason, the Phillies even after signing Zack Wheeler. The Athletics, Brewers, Padres, and Twins also jump to mind as potential landing spots.