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How Gerrit Cole got a $324M contract, and why he’s worth it to the Yankees

Another day, another record contract at the winter meetings.

Gerrit Cole pitches in the 2019 ALCS. Noah K. Murray-USA TODAY Sports

In the last few years the winter meetings would bore us. This year at the winter meetings, Boras.

On Monday at the Manchester Grand Hyatt in downtown San Diego, super agent Scott Boras was on the dais with the announcement of Stephen Strasburg returning to the Nationals on a record contract. Late Tuesday night, news dropped that another Boras client, Gerrit Cole, agreed to terms with the Yankees on an even larger record contract.

The terms are staggering for Cole: nine years, $324 million. How did this happen? What are the ramifications? There are several factors, and noteworthy items stemming from Cole’s record contract.

1. Boras played this beautifully

We knew Cole and Strasburg were going to cash in big time. Both were excellent pitchers entering free agency, and were in the unique situation of also being the top two pitchers during this year’s postseason. Both were Boras clients.

For Strasburg, the former No. 1 overall pick of the Nationals who was the 2019 World Series MVP, staying in Washington was a goal, made easier by the Nationals ponying up $245 million over seven years.

“For Stephen, for him to establish a legacy, and wear the curly W for his career was something that was very important for him,” Boras said.

By definition, players employ their agents (not the other way around) and ultimately can decide when and with whom to sign. But there’s a reason Boras holds court with throngs of reporters at every major offseason baseball gathering, including at this year’s winter meetings behind a backdrop of his own agency’s logo.

Boras is excellent at what he does, and by Strasburg signing first, that left only one truly elite starting pitcher left on the market. Teams that missed out on Strasburg would only have Cole left to bid on if they wanted a true difference-making ace.

It seemed a foregone conclusion when the offseason began that Cole would sign a record pitching contract this winter. But once Strasburg got a record of his own with seven years and $245 million, that pushed Cole into the stratosphere.

I should also note that Boras also represents third baseman Anthony Rendon, the best player remaining on the free agent market and another elite talent. He also negotiated $64 million over four years for Mike Moustakas, the poster boy of the last two stagnant winters with his one-year deals. This has been a fruitful offseason for Boras.

2. Financial titans decided to participate

The price always goes up when the behemoths want to spend. That wasn’t the case the last two offseasons, at least in the big ticket aisles. The Dodgers led the world in luxury tax for the first five full years of their new ownership group, but stayed under the threshold the last two seasons. The Yankees traded for Giancarlo Stanton’s massive contract after 2017, but otherwise steered clear of the mega free agents. New York avoided the competitive balance tax in 2018, and were just over in 2019.

This year both the Yankees and Dodgers were in the running for Cole, as were the also cash-rich Angels looking to add in manager Joe Maddon’s first year. That drove up the price for Cole, and, from what it sounds like, the length of the contract as well.

This pushes the Yankees well over the CBT threshold for 2020 — Cot’s Contracts estimates New York at $245 million once all is said and done, without any other additions — which is a departure from the last couple of years, and a return to the Yankees embracing their “Evil Empire” reputation.

Nine years is ridiculously long for a pitching contract, mostly because pitchers tend to break at some point. The only deal longer for a pitcher was signed by Wayne Garland, a 10-year, $2.3 million (not per season, that was the total) contract with the Indians in the infancy of full-scale free agency.

That you probably haven’t heard of Garland tells you pretty much how that deal turned out. He pitched only five more ineffective years in the majors before succumbing to injuries. His contract was such a surprise to even Garland himself, as he recalled a conversation with his agent to the Los Angeles Times:

“He said, ‘Wayne, I didn’t get you a million dollars,”’ Garland recalled recently. “I said, ‘Jerry, I’m sure you did the best you could.’ He said, ‘You got a 10-year contract for over $2 million.’ I said, ‘Jerry, I’m not worth it.’ He said, ‘Well, obviously someone thinks you are.”

Mike Hampton signed an eight-year contract with the Rockies in 2001 that became more known for his praising of the Denver school system (instead of simply saying he chose the best offer) than his performance on the mound. The other eight-year deal recently was Kenta Maeda with the Dodgers, a contract so incentive-laden that its total guarantee over the life of the eight years was $25 million, not even 70 percent of what Cole will earn in every season of his new deal.

So yeah, nine years is a big deal, almost unprecedented in MLB history, which adds to its largesse.

3. Holy crap, the Yankees are great

The Yankees won 103 games last year, and have averaged 98 wins the last three seasons, and just added arguably the best pitcher in baseball to their team.

New York already had a strong pitching staff overall — their 4.31 team ERA ranked just 14th in MLB, but adjusted for park and league their 94 ERA- ranked ninth — but didn’t have a true ace until adding Cole. The Yankees’ strength was their bullpen and they used it aggressively, such that New York’s starters pitched the fifth-fewest innings in the majors, averaging just 4.80 per start. Cole can help give that bullpen extra rest every fifth day.

Cole averaged 6.43 per start for the Astros in 2019 — ranking fourth in baseball — and he lasted seven or more innings in 15 starts. That matched the Yankees team total for the season.

The Yankees also get Luis Severino back, after he was limited to just three regular-season starts with rotator cuff and lat injuries in 2019. Severino started New York’s first game of the playoffs in both 2017 and 2018, and averaged 6.10 innings per start over those two years. The Yankees will be able to get more length out of the starters in 2020, which should help the bullpen with more rest leading to increased effectiveness.

New York was going to win a lot of games next season anyway. Now that they landed Cole, anything under triple-digits in the win column would be a surprise.

4. The fleeting nature of record contracts

Strasburg’s contract on Monday broke two pitching records: David Price’s $217 million with the Red Sox in December 2015, and Zack Greinke’s $34.42 million average annual value signed with the Diamondbacks that same month.

That Strasburg only had the record for two days isn’t all that surprising, nor rare. Everyone knew Cole — two years younger than Strasburg — was the big fish in this market, so it was just a matter of timing when he would sign.

Greinke’s deal in 2015 came just four days after Price, who also had the record for average annual value in his contract ($31 million) before Greinke broke it.

Thirty-one years ago, in February 1989, Roger Clemens cashed in with a three-year, $7.5 million contract with the Red Sox that not only made him the highest-paid pitcher in baseball, but the richest overall player, too. That took the title away from Dwight Gooden, who only one week earlier signed a three-year, $6.7 million deal with the Mets. Just one day after Clemens, Orel Hershiser surpassed him with a $7.9 million contract over three years with the Dodgers.

Maybe years from now, some pitcher will surpass Cole’s record contract, too. I only wonder if they can hold that mark for more than a few days.