FYI: I am the biggest A-Rod fan in the world. He is my favorite baseball player of all-time and almost single handily responsible for my love of baseball. With that said, I simply felt I should include a segment on him for those who would be wondering why he’s NOT on the list. The A-Rod contract was without any doubts - worth it.

Alex Rodriquez with the Yankees, 2 MVPs, World Series champ. Put fans in the seats at home and on the road. Anytime someone says he was a bad deal for the Yankees is showing hate for a great ballplayer.

Ngl, I'm not a Yankees fan (Go Cardinals 😆) but I appreciate you jumping right into the countdown without all the hoopla

HOW CAN AROD BE MENTIONED.WE HAVEN’T WON SINCE 2009. AROD CARRIED US TO THE THAT CHIP IN THE PLAYOFFS. 13 YEARS AND COUNTING

Maybe this is because of recency bias but I feel Chapman could be a honorable mention. While he did have very good seasons with the Yankees his constant issues off the field especially this past season and constant postseason failures could put him on this list for the 17m he was making a year

Did you realize that the window of 2004-2005 had a lot of really bad contracts with Pavano, Wright, Contreras and Igawa

It’s a shame about A Rod in pinstripes. If he had Derek Jeter’s personality, he would be thought of in the same breath as Babe Ruth, Joe DiMaggio, Mickey Mantle & all the Yankee goats. He was that good.

I used to say that "Kei Igawa" was Japanese for "sunk cost".

Dave Collins deserves a spot on this list too - not because of the 3 year $2.1 million deal which sounds like a drop in the bucket today, but because he was signed the same offseason they let Reggie Jackson leave as a free agent. the Yankees double-downed on the Dave Collins mistake less than a year later when overrated GM Gene 'Stick' Michael made one of the WORST trades in MLB history when he traded for Dale Murray and gave up Dave Collins with HOFer Fred McGriff and his 52.6 WAR along with Mike Morgan (who ended up with a 26.2 career WAR) who might have been even MORE valuable to the pitching poor 1980's and early 1990's Yankees than McGriff... but just think of all the prospects the Yankees traded away and all the bad free agent signings the Yankees made in those years chasing DH after DH and washed up SP after washed up SP when they could have had McGriff as their DH and Mike Morgan in their rotation, and used the money they wasted on those other players signing a real closer (or keeping Goose Gossage) which would have let them keep Dave 'Rags' Righetti in the starting rotation where he belonged (yes, he had a few great years as a closer but I'd rather have 200 innings of him as a starter than 100 inning of him in the bullpen)

Jaret Wright was also the reason Pedro Martinez didn't join Cleveland. For context, in 1997, the Indians and Expos were discussing a deal to send Wight and Bartolo Colon to Montreal for Pedro, but Cleveland got cold feet about moving Wright after he had a very good 97 postseason.

The Jarret Wright deal scares me now with the Rodon deal... same thing, a guy with injuries and ineffectiveness for years suddenly has a great year and a half - 11 games 2.00 ERA with Atlanta in 2003 and 32 games 3.28 in Atlanta in 2004 - it looked like he was finally healthy and Leo Mazzone (who was the best pitching coach in the game) worked his magic on him

I can remember a horrible FA contract from the old days. After the 1989 season the Yanks signed Pascal Perez to a 3-year deal worth $5.7 million. That was big contract then, especially for a 32-year old pitcher coming off a 9-13 season with the Expos. In two seasons with the Yankees he was 3-6 and pitched less than 100 innings.

Hey Dan thanks for the new video I watched today keep it up 👍

Frank Costanza: HOW COULD YOU GIVE 12 MILLION DOLLARS TO HIDEKI IRABU?!!!!

all of them were in response to Sox getting a ring lmao

re-signing 44 year old Roger Clemens for $4.5 million a month hurt the Yankees a lot more than Igawa making $4 million a year

moral of video. cashmans ability to evaluate pitching talent is horrific. lol and omg i remember the elsbury. i haaaated that signing. it made less sense than cashman trading for stanton.

The story goes the Yankees signed Carl Pavano to a 4 year, $39.95 million and Pavano was so pissed because he thought he was getting a nice round $40 million that he fired his agent, even after the agent offered to give him the $50,000 out of his own personal cut.

How many of these trades or acquisitions did little bryan steinbrenner make?

Fun video brotha💯💯💯

Arod was such an icon. I’m not even a fan but putting him on this list just completely mind boggles me

Stunned there is even actual game footage of Pavano! Similar to Jake Peavy for White Sox!

I have some vague recollections that Wright had a bad shoulder when he came to the Yanks. I definitely remember he was the sort of starter than it you got 5 innings out of a start, he had a good day.

How times change. In today’s game, 3yrs/$21M, 4yrs/$32M, 4yrs/$39M & 5yrs/$46M for pitchers is really cheap or the norm.

1. Jacoby Ellsbury 2. Carl Pavano 3. Ed Whitson 4. Jaret Wright 5. Kei Igawa That's my top five.

Can not wait until 10 years when you redo this video and judge is on the list

A-Rod does not deserve to be on this list, but they are right to honorably mention him as his PED association did sully the value of his contract in as much as they partly paid him to be the clean new HR king.

How quick we forget about Ed Witson and Steve Kemp. These were big dollar contracts in the 80's and their performances makes Aaron Hicks look like an allstar

What’s funny is you say that that “the offensive production was just not there as he slashed a mere .264/.336/.386 with a .722 OPS” but can you imagine how happy we would have been last season if Aaron Hicks or Joey Gallo had put up those exact numbers instead of what we got?

I get why you didn't put A-Rod on the list, but did ANYBODY think the 10 year deal (taking him into his 42 year old season) was a good one? It's a very rare baseball player who stays healthy to 40 or beyond. If they'd paid less per year, then maybe it would have been okay, because they could eat it when he was totally ineffective in his "old" age, and eaten his full year suspension. But PR damage was even worse. But you're right. Without him, it's very likely we'd still be 26-time champions. People point at Matsui and say "he's why you won", but I point at A-Rod and say "he's why we were there."

Haven't watched but Carl Pavano is probably on the list

Failure on Elsbury then failed again on signing Hicks to a long term deal. Arod was a huge part of '09 but if we used Arod's money on 2 or 3 other good players it would have made up the difference and been better in more years than just '09.

Bro, I know you like arod but appreciate you put him in video

That Brian Cashman really knows pitching. 🙄🙄

Because of the shortened 2020 season, all active player salaries were prorated for the 60 games played. As I recall, this prorated salary didn't apply to released or medically retired players. Because of this, Jacoby Ellsbury was the highest paid player on the 2020 Yankees.

Lol @ “he had never used While wearing pinstripes.” Dude never stopped. How he ever think no one thought he wasn’t using

The signing of Ellsbury was the most desperate rebound move ever. It was like the Yankees got dumped by their long-time lover (Cano) and immediately proposed to the best option sitting at the bar. Ellsbury was a nice little leadoff hitter in Boston, but really only had one standout season in 2011. The Yanks knew what they were getting with him, but still floated a fortune his way as a consolation prize after a miserable - by their standards - 2013 season where they missed the playoffs for only the second time since 1993. It was a franchise in disarray. Jeter was retiring. A-Rod had been suspended again for another PED violation. They had no identity and were surely banking on Cano being the face of the franchise moving forward. Once he left though, they hit the panic button with Ellsbury. His first few seasons in pinstripes he actually put up similar production to what he had been doing in Boston so it is not even like there was this huge regression. They simply overpaid for a decent leadoff hitter who played good defense. The backend of that deal is where it fell completely off the rails with injuries and his inability to even get on the field which immediately promoted him to Carl Pavano status in the eyes of the fanbase. An absolutely ridiculous contract where all the blame falls on the Yankees management. However, after the last few years of Aaron Hicks and Joey Gallo in the outfield, that 2014 Ellsbury season suddenly looks pretty damn impressive.

Great list....awesome job.

I am still waiting for some position player movement, other than the pitcher they signed still have not improved the lineup. Cannot count on Judge to hit 60 or Rizzo to hit 30, need contact hitters with a little pop.

I still think Ellsbury is dead and buried under second base at the Yankees spring training field

While the ARod deal was not great, calling it a free agency signing is a bit of a reach. They acquired him via trade from Texas and when he opted for FA, he knew he was going to stay in New York. Heck, he opted out at the end of October and they had outline the new deal like two weeks later. I don't think there was any real thought from the Yankees or Rodriguez himself that he was actually going to test the free agent market.

Idk if you are like this but I can’t belive judge is still on the Yankees

Honorable Mentions: Donaldson and Hicks

How many RBI, Homers, scored runs, doubles, and singles, he got under his tenure as a Yankees. Which other players had similar or better than ARod? Nobody. So, how bad was his contract with the Yankees?

Thing is teams like the yankees can have a couple bad deals and not blink, they can have 100 million in payroll sit on the DL and they can be fine. Which is why they can take more risks then most other teams, which is also why they are in the playoffs more times then not. Not to mention they are in the number 1 TV and Radio market which pays for all the bad deals, before they even sell one ticket.

Hey where is Mr. May A. Judge on this list? Should be number 1! A Rod won a WS in 2009 if I remember correctly and Mr. May well he did hit a ton of homers last year against some of the toughest Triple A clubs in the American League.

Igawa was so so clearly a panic/response move to the Sox winning the Dice-K contract. Everyone knew it. And what people forget about Ellsbury is that they tried to give Choo a similar contract which (thank god) he turned down. Cashman is so overrated it’s ridiculous.

1. ellsbury 2. pavano 3. sabathia extension 4. igawa 5. contreras HM: hicks (barring turnaround), brian mccann, kyle farnsworth, hideki irabu, rondell white

They don’t win in 09 if not for Matsui, so think again. BTW Johnny Damon is the runner up followed by ARod. As far as failures Ellsbury wears the crown followed by Pavano.

As a Red Sox fan, I remember thinking that they did the right thing by letting the Yankees sign him for that absorbent amount of money. He clearly wasn’t worth it at the time.

More vids like this plzzzz

Ellsbury wasn’t even used correctly in the lineup like why have him in the number 3 spot when he had speed to be a leadoff hitter or number 2 behind Gardner who was also was peaking at the right time. But they put jeter in the 2 spot mister king of double plays , always hit into one and defeat the purpose of use of him. Nowadays the Yankees are still struggling of how to use “speed and contact” in their lineup after just making power hitter who barely runs or strikes out a ton.

lol I never knew about that Jarret Wright contract wtf man that’s insane

Why isn't Kevin Brown on any worst list?

Worst is keeping Cashman as GM

I will go down, but hopefully will go up with the Yankees. I'm diehard.

It was Ellsbury getting hurt while rehabbing for me.

Dude, you forgot to add that Contreras won the WS with the White Sox....

My favorite part of the video was whenever Dan says something sarcastic.

Boston is dying for another prospect like Ells. To have a leadoff hitter like that similar to a lead Ace. Produces a trickle down effect. The Sox know this. Curious how Ellsbury staying in Boston for 2014 and beyond goes down in an alternate universe.

80’s had some terrible signings. Winfield, Tartabull, Barfield, Hawkins, LaPoint…took a whole decade to get rid of all those stiffs.

Igawa was not that bad a signing either, international free agents are all a gamble. the posting fee was the only bad part but he only made 4 million a year and they were able to find a loophole to banish him to the minors so it did not effect the luxury tax

Do you even remember Kevin Youkilis? Would you want to? I guess 1 year at 12 million doesn't rank up there with this fab five as putrid signings go. But if you want to talk about a signing who did absolutely, positively NOTHING then he's your guy. At least Ellsbury had one decent year.

Ellsbury signing is one of those I knew would be bad.

That name Ellsbury just makes me extremely upset 😤.

“All Time”? Ed Whitson Danny Tartabull Steve Kemp Dave Collins

I am going to disagree with AROD... he wasn't injury prone, but just a troublemaker. At least he put great numbers while he was with the Yanks despite his shit numbers in the post season, but at least he gave us that 1 world series ring. Personally I think Jason Giambi's contract was worse than AROD. As soon Giambi got caught using roids, his numbers started to decline and it was nothing like when he was in Oakland.

I was like WTF are they thinking with both Wright and Ellsbury

We win a ws idgaf what the deal looks like at the end.

Any former Marlins pitcher the Yankees signed should be on this list.

I would have Danny Tartabull on this list, although in hindsight with current metrics (WAR, OPS) his first two years of the deal were not as bad as fans thought at the time... he went from .316 30 HR 100 RBI in KC in 1991 to .266 25 HR 85 RBI in NY in 1992 but his OPS was still a great .898 and his WAR only dropped from 4.4 to 4.1 partly because he had less ground to cover at Yankee Stadium in RF than in KC and his dWAR improved from -2.1 to -1.4... still, he was a horrible fielder on a team with an aging Don Mattingly and a still promising Kevin Maas already entrenched at 1B and DH at the time of the signing - the 4 year deal at $5.2 million set the team back more financially than a $36 million a year deal would set us back now in today's market as he was second only to Bobby Bonilla $6 million in the game. the money could have been used elsewhere the next offseason to be able to get Greg Maddux

You are leaving out Arod's last 2 years on the team. He and Tex had combined for like 3 hrs and both were under a .200 BA. Tex retired letting the Yankees off the $$ hook. Arod wouldn't do that. He became a baseball "consultant" and collected the rest of his contract. Even though his play was dog sh_t he wanted to get paid. That is why he will NEVER go down as a beloved Yankee.

Wright and Pavano drove me nuts and I’m a Mets fan. Those guys were never good!

The jeter contract after 2009 was garbage. He had one good offensive season 2012 and was dreadful defensively at SS.

This going back many years how about Don Gullet. I don’t think he pitched a half a season for the Yankees.

What about Don Gullet??

I never understood the Ellsbury deal.

Do draft picks next

Ahhh..and whay you think about Jhonny Dammon?

Contreras wasn't a bad signing, we kept him away from Boston, he had a great first year in 2003 and a bad half season in 2004 before he was traded but rebounded to have a very good year in 2005 getting MVP votes and an all star season in 2006... we weren't patient enough with him, same as Sonny Gray, Nate Eovaldi and all the other pitchers who come here, get booed and traded and become stars again elsewhere. . we as Yankees fans need to stop doing this. gonna happen with Montas now too, mark my words. he'll be out of pinstripes and will return to all star form

There is a level between Double A and Japanese baseball.

Everyboy and their mothers knew the #1.

Why am I not surprised that a Yankees fan is practically praising A-Rod

Did A-Rod help Yankees win a World Series?

Imagine A rods career stats if he didn’t get tht suspension

Hidek Irabu was worse to me

Bruh, could you imagine goin into 2020 with Elisbury LMFAOOOO

Anyone that says A-Rod is a Clown. A-Rod is one of the best players in MLB History.

Geez, I actually remember Jacoby being worse.

I wouldn’t put a rod on this. It’s not like arod couldn’t perform without roids. A rod was a fan favorite

Texas paid most of Alex Contract.

Arod was an icon stop the cap even with the controversies one of the best players in history. - not a Yankees fan.

Is the big guy getting his 10% of all MLB revenue??

Irabu?

I hope Judge can hold up starting his contract at 30 years old love the guy on the team but man what a big deal

anyone forget eddie whitson steve kemp melidio perez

Kei Igawa was hands down the worst move ever. Who was the genius that said “ we must sign him, he’s the Japanese Nolan Ryan!” He got 2 wins for $46M.

Kevin Brown... need i say more ? lol

Na dude.... A-ROD saved the yankees in 09. Remember us being 0-8 thru the first half of season vs the Boston? I do. That monster HR in xtra innings? Then the post season. So no get him off that list

Ur the best