It's now officially been 20 years since the dynasty in the Bronx died. Since beating the Mets in the 2000 World Series, the Yankees have won just one championship in that time. Their 2009 World Series was a stand-alone title that was fueled, in large part, by the desire to christen to the new ballpark in the Bronx that season.
The Yankees ownership and front office is home watching the World Series and doing their post-mortem meetings on what went wrong and how they can get back on track to win their 28th World Series title. Those meetings, usually held in Tampa, are virtual this year because of the coronavirus pandemic, which drastically changed the landscape of the game this year and threatens to impact them for years to come.
There is a long list of decisions the team will face once this year's World Series ends. Free agency begins immediately after the series ends every year and then there is a five-day grace period before teams can sign free agents, but teams can talk and make trades during that time. The end of the World Series starts the clock on team and player options, but they have five days to make a formal decision. They also have five days to decide on if and who they will make a qualifying offer to. Considering that this year's qualifying offer carries a $18.9 million contract, that's no easy decision.
First and foremost, however, the Yankees have to figure out where they want their payroll to be in the 2021 season.
All indications are the Yankees are looking to get under the $210 million luxury tax for next season. Managing partner Hal Steinbrenner signaled that the team would to cut costs last December, well before the coronavirus pandemic hit and cut the MLB season to 60 regular-season games without fans. Steinbrenner would not disclose his financial plans, but in an radio interview earlier this month, he said the Yankees had lost more money than any other team.
That decision will be the basis for all moves this winter.
So starting off, the Yankees have to decide on Zack Britton's $14 million option for the 2022 season. Britton is due $13 million for 2021, but if the Yankees do not pick up the 2022 option, Britton can immediately become a free agent. Britton has been solid in his two and a half seasons with the Yankees as Aroldis Chapman's set-up man — and as the closer when Chapman was sidelined by COVID-19 as well. This should be a no-brainer for the most recognizable franchise in the game, but as the country goes through the greatest economic downturn since the Great Depression, it's up for debate.
Other players with options this winter are Giancarlo Stanton, who almost certainly will not opt out with seven years and $218 million remaining on his contract. The Yankees also have options on contracts for Brett Gardner and J.A. Happ.
Next, the Yankees have to decide on which of their free agents they will let walk and which they will try to keep via a qualifying offer.
The American League batting champ, who also led the majors in batting average, LeMahieu has arguably been the Yankees most important player over the last two years. The 32-year-old is almost certainly going to be one of the few free agents who gets a big contract this winter and will not pay what some executives are calling the "COVID tax" in free agency.
Still, the Yankees will certainly offer him a one-year qualifying offer. After all, $18.9 million would be a bargain for LeMahieu. He will likely decline, but recent history and the uncertainty of teams' financial situations could make the free agent market a little more unattractive. Masahiro Tanaka, who just completed his seven year deal with the Yankees, could be another player the Yankees could easily put the qualifying offer tag on with their rotation so uncertain after Gerrit Cole. Jordan Montgomery, Deivi Garcia and Clarke Schmidt are the only starters under contract for next year who were starting in 2020. Garcia and Schmidt are still developing and whether they will start 2021 in the big leagues is not certain.
Tanaka has been a solid starter for the Yankees and while this year's postseason may be concerning, the circumstances of the starts have to be taken under consideration.
James Paxton, who ended the season on the injured list, would be a big risk to put a qualifying offer on. There will be concern about his health after having started the year with a back surgery and ending it with a flexor strain in his left forearm. The Yankees, however, have the best insight into Paxton's health, so it would be an educated guess.
If the player declines a qualifying offer, the Yankees would get compensation in the next draft, so there is some reward to the risk.
These are just the first questions the Yankees face once the World Series ends, but they are the foundation to their attempt to get back to their first World Series since 2009.
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