Eleven years after selecting him in the first round of the 2008 draft, the Yankees finally landed Gerrit Cole on Tuesday night. The free agent right-hander agreed to a record-breaking nine-year contract worth $324 million. The deal reportedly includes a full no-trade clause and Cole can opt out following the fifth year. 

Here are the five largest pitching contracts in baseball history in terms of total guaranteed money:

  1. Gerrit Cole, Yankees: 9 years and $324 million
  2. Stephen Strasburg, Nationals: 7 years and $245 million (signed Monday)
  3. David Price, Red Sox: 7 years and $217 million
  4. Clayton Kershaw, Dodgers: 7 years and $215 million
  5. Max Scherzer, Nationals: 7 years and $210 million

Cole's $36 million average annual value is a new record for any player, pitcher or position player, surpassing Mike Trout's $35.54 million. Roughly 48 hours ago the largest pitching contract in history was $107 million less than it is right now. Pretty crazy.

Adding a starting pitcher was the clear top priority for the Yankees this offseason and they addressed that need in the best way possible. Cole is arguably the best pitcher in baseball and he is only 29, so he's right smack in the prime of his career. There was no better possible addition and all it cost the Yankees was money (and two draft picks and some international bonus pool space).

Now that Cole is set to wear pinstripes, the Yankees can move on to other pressing business. Here is what New York still needs to accomplish between now and the start of spring training in 10 weeks.

Find a center fielder

Brett Gardner is likely to be New York's next free agent signing. USATSI

Aaron Hicks had Tommy John surgery in October and will be sidelined until the middle of next season. The Yankees do not have a center fielder on their 40-man roster at the moment, with fourth outfielder Mike Tauchman the only 40-man roster player capable of playing the position on a part-time basis. Center field is now priority No. 1.

Of course, the Yankees are almost certain to re-sign Brett Gardner. Gardner, a career Yankee, was the club's primary center fielder this past season as Hicks battled through numerous injuries. He is pretty clearly the best center fielder available in free agency. Here are projected 2020 WAR totals for unsigned free agent center fielders (via FanGraphs):

  1. Brett Gardner: 1.9 WAR
  2. Kevin Pillar: 1.4 WAR
  3. Jarrod Dyson: 0.5 WAR
  4. Cameron Maybin: 0.3 WAR
  5. Billy Hamilton: 0.2 WAR

Even at age 36, Gardner is the best available free agent center fielder, and it's not all that close either. He's made it no secret he wants to finish his career in pinstripes -- "I've always been open about wanting to play my whole career here. I hope I get the opportunity to do that," Gardner said after the ALCS -- and a reunion on a one-year contract feels inevitable.

For what it's worth, the New York Post's Ken Davidoff reports the Yankees made Gardner a new contract offer last Friday, and SNY's Andy Martino says a signing will probably happen soon. The Yankees need a center fielder, so re-signing or replacing Gardner is a top priority now. All signs point a reunion.

Dump Happ's salary

As noted by our R.J. Anderson, the Cole signing brings New York's projected 2020 luxury tax payroll up to $245 million, well above the $208 million threshold and the $228 million second tier, and close to the $248 million third tier. Each tier brings higher tax rates and, as a repeat offender (the Yankees will pay luxury tax for 2019), the Yankees will have even higher tax rates.

"It's a big deal. It's something we'd certainly prefer not to do, because there are June draft ramifications. There are numerous ramifications," owner Hal Steinbrenner said earlier this month when asked about exceeding the $248 million luxury tax tier. The Yankees are at $245 million now and that's without re-signing or replacing Gardner, or making any other moves.

The easiest and maybe only way for the Yankees to clear payroll is trading left-hander J.A. Happ. Happ, who threw 161 1/3 innings with a 4.91 ERA this past season, is owed $17 million in 2020, and the Yankees are actively shopping him. With Cole aboard, New York has the rotation depth to move Happ:

  1. RHP Gerrit Cole
  2. RHP Luis Severino
  3. LHP James Paxton
  4. RHP Masahiro Tanaka
  5. LHP J.A Happ
  6. RHP Domingo German (awaiting suspension under MLB's domestic violence policy)
  7. LHP Jordan Montgomery
  8. LHP Michael King
  9. RHP Jonathan Loaisiga

The Yankees can trade Happ and plug Montgomery, who returned from Tommy John surgery late in 2019, into their rotation as the No. 5 starter until German returns. They could even trade Happ and sign a cheaper fifth starter. Someone like, say, Homer Bailey or Martin Perez may be able to replace Happ's production at a fraction of the cost.

Earlier this week the Angels gave the Giants infield prospect Will Wilson, the No. 15 pick in this year's draft, to take on Zack Cozart and the $12.167 million remaining on his contract. Similarly, the Yankees would have to add a sweetener to dump Happ's salary, though an innings-eater is presumably more desirable than an infielder who has been injured and ineffective the last two years.

The Blue Jays are among the teams to express interest in Happ, reports SNY's Andy Martino, plus the Angels, Brewers, Phillies, and Twins could get involved as well. The Angels and Phillies pursued Happ as a free agent last winter and could look at him again as a back of the rotation option. The Yankees will have to give up a young player to do it, but moving Happ is possible.

Shedding Happ's entire $17 million salary would get New York's luxury tax payroll down to $228 million. Realistically, staying under the $228 million luxury tax tier is impossible. They have to re-sign or replace Gardner, and every injury call-up equals more dollars on the payroll. Unless they trade a reliever (Zack Britton? Adam Ottavino?), there's no way to get under the $228 million tier.

Trading Happ would give the Yankees about $20 million in wiggle room under the $248 million luxury tax tier, however, and that's more than enough to re-sign or replace Gardner, make other complementary moves, and leave space for in-season moves. Trading Happ is a near certainty at this point. It's just a question of which young player the Yankees will give up to make it happen.

Replace Gregorius?

Gleyber Torres is poised to take over at shortstop for the Yankees. USATSI

A few hours before the Yankees signed Cole news broke that Didi Gregorius had signed a one-year, $14 million contract with the Phillies. Gregorius returned from Tommy John surgery this past June and had a down season. He'll look to rebuild his value with former manager Joe Girardi in Philadelphia, then test free agency again next winter.

Unlike Gardner in center field, the Yankees do not have to re-sign or replace Gregorius at shortstop. They can replace him internally with Gleyber Torres, and put DJ LeMahieu at second base full-time. This past season the Yankees were able to play Gregorius at short and Torres at second, with LeMahieu rotating around. That layer of depth was valuable, but also a luxury.

Given the team's payroll situation and the lack of desirable free agent middle infielders, replacing Gregorius could prove difficult. Jose Iglesias is the best shortstop capable infielder on the market now, and trading prospects for someone to play behind Torres and LeMahieu probably isn't the best use of resources. Replacing Sir Didi is a possibility. It just seems unlikely.

Improve on the margins

Like every other team the Yankees will spend the next few weeks trying to make upgrades all over the roster, no matter how small. For example, the Yankees have interest in Royals reliever Tim Hill, according to MLB.com's Mark Feinsand. That's likely because they believe he's better than the 39th or 40th man on their 40-man roster. Any little upgrade is worth making.

The Yankees have proven to be very good at identifying undervalued players. They got Tauchman in a minor trade at the end of spring training this past season. Maybin and Gio Urshela came over in cash trades. David Hale signed a minor-league deal and the team's analytics group helped him add velocity and spin. Those four players combined for 9.3 WAR in 2019.

As always, the Yankees could use more pitching depth heading into next season, and it stands to reason they will bring in a backup catcher with Austin Romine now a free agent. At the very least they figure to add a non-roster type to compete with backup catcher candidate Kyle Higashioka in spring training. Small moves that improve the 30th to 40th spots on the 40-man roster, basically.

It is not easy to improve a 103-win roster but the Yankees managed to do that with Cole. He gives them the no-doubt ace-caliber starter they've lacked since their 2017 return to prominence. Re-signing or replacing Gardner and salary dumping Happ are the next orders of business. Then the focus will shift to smaller upgrades all over the roster. The heavy lifting has been done.