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Yankees GM Brian Cashman got the nod from Hal Steinbrenner to open the team's checkbook, and do whatever it took to land this year's top free agent in Gerrit Cole.

The result? The richest contract ever given to a starting pitcher in MLB history at $324 million over the next nine seasons.

As Cole takes the stage at Yankee Stadium on Wednesday to don the pinstripes for the first time and officially be introduced as the Yankees' new ace, we're reminded of just how powerful this organization can be when they really want someone on their team.

In fact, this isn't the first time Cashman set a new record for a contract given to a pitcher. CC Sabathia broke that when he signed his massive (at least at the time) $161 million deal over seven years. And, of course, deals of that magnitude make the pitcher's performance that much more crucial.

Because if it turns out bad, it's money thrown to the wind.

Cashman has had his fair share of dud signings to go along with his shining stars he's shelled big bucks to. Here are some of the best -- and the worst -- big-money signees in Cashman's tenure:

1) CC Sabathia

As we mentioned before, Sabathia was not going to slip through Cashman's fingers, so he signed him to a record deal. It was much like the case of Cole, and the Yankees will certainly hope Cole's pinstriped journey sees the same results as Sabathia.

In his first season with the Yankees in 2009, Sabathia anchored the rotation all season long and helped capture the team's first World Series victory since 2000. He was also a three-time All-Star with New York in his first four seasons, while pitching to a 3.81 ERA over his 11 years with the team.

He battled through injuries late in his career, but Sabathia always managed to come through when the Yankees needed him most, especially in the postseason. Never mind the fact that he was the 2009 ALCS MVP after posting a 1.13 ERA in two starts, but think of how much more recently in 2017 he pitched a critical Game 5 win over the Indians to advance from the ALDS. He had a 0.96 ERA in two starts in that ALCS as well.

Sabathia was beloved by Yankee fans from Day 1, and received a more-than-deserving standing ovation at Yankee Stadium this season following his final time on the mound, as he walked off into the sunset. He should be a Hall of Famer someday, which is why all his accolades slightly beat the next person on our list.

2) Mike Mussina

"Moose" is a Hall of Famer as of this year, and it is very well deserved. Cashman dished out $88.5 million to him over six seasons back in 2001, and he would remain a Yankee till the day he retired in 2008 (he should've waited another season to capture his only ring).

Mussina was a model of consistency during his Yankee tenure and even better in the postseason, where he flipped into another gear. He owned a 3.88 career ERA with the Yanks that spanned over 1553 innings (249 games). His postseason numbers are even better with a 3.42 career ERA over 23 games (21 starts).

Moose didn't go into the Hall as a Yankee due to his years with the Orioles before he switched teams in the AL East. But Yankee fans will always remember the contributions Mussina made to try and bring the World Series trophy back to the Bronx.

3) Masahiro Tanaka

Not all of these signings are off the Yankees just yet. Tanaka was bid on by many, including the Dodgers, as he wanted to make the leap from Nippon Professional Baseball in Japan to MLB. Cashman & Co. won that bidding war with a seven-year, $155 million deal that Tanaka signed in 2014.

And it has been worth it.

Tanaka owns a career 3.75 ERA in just over 1,000 regular season innings thus far despite some bumps along the way. He hasn't necessarily been the lights out ace Cashman hoped he would've been, but he has consistently eaten innings over his six seasons in pinstripes.

The postseason is where you see that ace-like mentality come to the mound with Tanaka. He has a very impressive 1.76 ERA in eight postseason starts that includes three solid outings this past year in the ALDS and ALCS.

He's in the final year of his deal now, and if he continues pitching the way he has all these years, the Yankees could bring him back for what would likely be a less lucrative agreement.

4) AJ Burnett

After these three, the list takes a pretty big dive. Sabathia wasn't the only big signing by Cashman before that 2009 season, as Burnett came on with a five-year, $82.5 million deal. He wasn't exactly dominate in his years with the Marlins and Blue Jays, but he was a solid No. 2 option for Sabathia.

However, he didn't live out the entirety of that contract. After posting a respectable 4.04 ERA in '09 with a decent postseason showing for the first time in his career, Burnett slipped with a 5.26 ERA in 2010 and no improvement at 5.15 in 2011.

The Yankees would eventually deal him to the Pirates before the 2012 season to unload some money off payroll, but at least he captured the only ring of his career during that short time.

5) Randy Johnson

When you're one of the best lefties to ever play the game, you can still get big money passed your 40s.

That's exactly what Cashman did in a deal with the Diamondbacks to acquire the flame-throwing left-hander in 2005. He also signed him to a two-year, $32 million extension at age 41 following an insane 2004 season that saw him put up a 2.60 ERA. Johnson didn't put that up with the Yanks in his debut season, but through 225.2 innings, he had a 3.79 ERA with 17 wins to his name.

The Yankees didn't do much that postseason, losing to the Angels in the ALDS, where Johnson produced a 6.14 ERA through two games. But at 42 years old in 2006, Johnson's age came through with a 5.00 ERA through 33 starts. The Yankees didn't extend him after that, but he played three more seasons before calling his Hall of Fame career quits.

6) Jose Contreras

It was a story bigger than baseball itself, and it just so happened that Cashman was the man who landed the Cuban defector at age 31. Contreras finally made his way to MLB in 2003 when the Yankees signed him to a four-year, $32 million deal.

But it was a career that didn't last long in pinstripes.

Contreras produced a 3.30 ERA in his first season (18 games), but the Yanks traded him to the White Sox in 2004 after he put up a 5.64 ERA through 18 starts. He would go on to play in one All-Star game with Chicago and spent time with the Rockies, Phillies and Pirates as well.

7) Jaret Wright

It was a career year for Wright in 2004, when he pitched to a 3.28 ERA with the Braves over 32 starts. So Cashman just had to have him in free agency, hoping he would continue that trend moving forward.

Instead, Wright reverted to his old ways after signing a three-year, $21 million deal with the Yanks. He had a 6.08 ERA in his first season followed by a better, but not really improved 4.49 ERA in 2006. He moved on to the Orioles that following season, and after three bad starts, he didn't make it back in the league.

8) Carl Pavano

Yankee fans might cringe reading this one, but it was a big deal for Cashman at the time Pavano signed the dotted line.

Much like Wright, Cashman saw the opportunity to sign someone coming off a career year, with Pavano making the All-Star team after producing a 3.00 ERA for the Marlins. But what makes this worse is Pavano was expected to be they're dynamic No. 2 starter next to Johnson, and that wasn't the case at all.

He had a 4.77 ERA in 17 starts before a shoulder injury ended his season. Then, Pavano had to miss the entire 2006 season, and didn't rebound in his two seasons after that, with a 5.77 ERA in his final Yankees year in 2008.

9) Kei Igawa

Finally, rounding out the group is someone that should be chalked up as one of Cashman's worst free agent signings in his Yankees tenure.

Igawa, like Tanaka, was highly touted during his career in Japan. When he was looking to make a leap to MLB, the Yankees had to pay a $26 million posting fee just to talk about a potential contract with Igawa. Luckily, it wasn't burnt money, but Cashman probably wishes that's all he spent on him.

Igawa signed a five-year, $20 million deal that we'll just say is $46 million with the posting fee attached. And what did New York get out of it? Well, how about 16 total games with a 6.66 ERA before the Yankees pulled the plug on his MLB dream.

Ouch.

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