The Career of Rick DiPietro

With some big contracts on the way over the next few days, I wanted to talk about one of the longest contracts the NHL has ever seen and why it was signed at the time.
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[@mattblom3990]

DiPietro was so memorable. He replacing Luongo as uber-goalie. Then at the time it was signed, a 15 year contract was unthinkable. What an albatross but not Rick's fault.

[@anowhereguy2521]

I saw the title and immediately thought "Well, this is not gonna be a very long video..."

[@BoyNamedSue4]

Mike Milbury being in charge tells you everything you need to know

[@boneseyyl1060]

Milbury is literally the dumbest guy in all of sports. I mean he can't even put a full sentence together. He was a goon on the ice and he was a goon in the GM office. Islander head office - What are your qualifications for GM Mike? Mike - Well...uh... I played hockey and punched a lot a guys in the face! Remember that time I went up in the stands and chased a fan with my skates on ..... Islander head office - Just what we are looking for.

[@Slapshot55]

Milbury actually refused to sign Dipetro to that contract and lost the GM job over it. Man actually got fired for the only good move he tried to make as Isles GM

[@nowaybruh145]

That was a Garth Snow deal. They were besties Rick's first years in the show. The owner Charles Wang (I think) loved Ricky. LOVED. So when Rick's best friend got promoted to GM, this mega deal was essentially a buddy buddy deal between the three of them. Source: I was hanging out with Rick in Winthrop that summer.

[@nowaybruh145]

@@Slapshot55 exactly. See my other reply on this thread

[@beardymcj2026]

Rick DiPietro was one of the most fun goalies to watch. The reason is, he played the puck a lot like Marty Brodeur and Marty Turco. The only thing is...he wasn't anywhere near as good at it as those two, and often hilarity ensued

[@NolanEgbert]

He was a wild card with the puck as a rookie but by around 2007 he really became a fantastic puck handler. Problem was that once his knees went he couldn't get to the puck quick enough and lost one of his biggest x-factors

[@taskdon769]

So, Mike Smith basically?

[@thedoorscreatedpsychrock5795]

But unlike Brodeur, Rick DiPietro is easily the greatest goalie of all time 👌

[@isaacwest276]

I will genuinely miss watching Mike Smith as an Oilers fan.

[@PJH-vd7ve]

As a long-time Islanders fan I only recently realized how "descent" DiPeitro was. The guy spent 10 on-and-off years in the NHL. He made the All-Star game and played for team USA. He was a reliable goalie when he was healthy and was often the bright spot in the nightmarish 90s-2000s era. He was on the same level as both goalies who make it to the NHL and also managed to do things only a certain few can. BUT he was the first overall pick of the draft which welcomed the new century. He was only the second goalie to be drafted first overall (since then only Fleury joined the club) and was high noted for his incredible stick worth and hybrid goaltendinf style. He was supposed to revolutionized the position and lead the Islanders out of their slump. And honestly, those were very high expectations which were not fair to him. Goalies are goalies. It's almost never a good idea to draft them high (there are exceptions of course) because so many things later one factor as to how good a goalie will be. Just because he failed to be an Islanders legend doesn't mean he was a bad NHLer. Too much was asked of him and it's worth noting that injuries are ultimately what brought him down and not a lack of quality when he was healthy. And the contract was obviously not his fault. Who wouldn't accept such an incredible deal. The blame for what rests on Garth Snow and nobody else. So yeah, I've come to accept that DiPietro was a descent player who simply got injured and failed to achieve incredibly unrealistic expectations.

[@MrOctober44]

The deal has nothing to do with Garth Snow. Millbury was the GM. In fairness to Millbury it was Wang's idea to give those giant contracts. He definitely had a lot of bad luck in his career. Unfortunately he'll forever be a punchline, which is really unfair.

[@NolanEgbert]

@@MrOctober44 Milbury was gone before the 15 year deal. It was all Charles Wang and was a prerequisite for anyone who wanted the Isles GM job. Neil Smith refused and was promptly fired and only Snow was willing to do it for the job

[@retrobowlenthusiast]

*decent

[@stevecampbell9670]

@@retrobowlenthusiast I dunno, he may be on the nose with "descent". As in his career had a rapid descent after signing that huge contract.

[@yoholmes273]

Rick was trash . Imagine having prime Luongo and drafting this clown numero uno overall. Why do you think the Islanders were garbage for 3 decades? Guys like this is exactly why.

[@atex6175]

Grew up with Rick played hockey with him until 13 the kid was a phenomenal athlete. He was a nasty pitcher lefty threw gas with good control.

[@YinzerChrist]

Rick DiPietro is the reason I wanted to become an agent

[@HDreamer]

I remember reading an article in german sports media, when at the end of his career he tried to play for a german 2nd Division club, so not even DEL, but below that. By that time his body was so broken, that he played like 1 game for them.

[@Gagne87Fixxer]

When people tell me Dipietro is a bust, I tell them that the injury that derailed his career happened during the All-star week-end…

[@yoholmes273]

Why that is cool story, remember that every team HAS to have an "all-star". Dipietro is the epitome of what a BUST is all about.

[@closethockeyfan5284]

Not a bust, rather a man of glass, like Beau Bennett. It happens to some people. 🤷‍♂️

[@yoholmes273]

@@closethockeyfan5284 "Made of glass" = BUST

[@JarradBruessel32]

@@yoholmes273 at that time they didn't actually. That was a rule made later on

[@TheBigfootsfeet]

I’ve always said that he wasn’t a bust, but was busted by the islanders

[@swy334]

He was very good in the 2007 playoffs. Playing against the stacked buffalo sabres who won the president's trophy (weird saying that now)

[@jetswhiteout961]

Buffalo was good?

[@aralornwolf3140]

@@jetswhiteout961 , Some bad teams actually were decent at some point... as long as they aren't in Arizona.

[@DJGuRu0071]

@@jetswhiteout961 they had fucking briere on their team yeah they were good

[@ozzydo2314]

Ovechkins 13 year contract may have been the greatest long term contract in history. A contract many scuffed at

[@aralornwolf3140]

They should have signed a 20 year contract at that time... would have saved them even more money, rofl.

[@GvirusUser]

The most memorable thing about Depietro was when he challeneged the Pens goalie Brent Johnson to a fight and Johnson punched him in the face and knocked him out.

[@ScaryRevenant]

That and those pink pads he wore lol

[@AyeThatsHandsomePete]

And broke his jaw.

[@nseifner]

Damn beat me to it. I lost my shit when this happened live. I was just yelling at the TV, No way this is happening OMFG YESSSS!

[@WillNDIrish]

That fight was a great representation of DiPietro’s career

[@GvirusUser]

@@nseifner wasn't it the same game both teams just went at it and two penguin players fought one guy? I remember there being a lot of penalties from that game.

[@Bird.Man1134]

He’s still on the radio, his show is “DiPietro & Rothenberg” on 98.7 ESPN Radio in New York

[@bexxgenx3165]

Poor Ricky. If it wasn't for that poor body all rickety and broken I think he would have lived up to that contract! He had greatness written all over him. One of the most beautiful butterflies I've ever seen too.

[@samuelbenton469]

My favorite goalie story ever.

[@InsignificantNick]

I'm actually surprised by his win/loss record. It's not...terrible.

[@NolanEgbert]

DP dragged some bad Isles teams kicking and screaming into the playoffs and kept them relevant when they had no business being even close to competitive

[@fphlflash]

"Fra-GEE-ley!!!" Had some good streaks and tons of potential, just like Chris Chandler in the NFL. Had the durability of shattered glass, just like Chris Chandler in the NFL....

[@barzdown1437]

I heard from someone who used to be on the islanders training staff that DP had used steroids at a young age which would explain all the injuries

[@skiddy3715]

I live in the area where I can hear him in the car now and again, and he's very good on there.

[@donaldpaluga]

Funny his first time with the Bridgeport Sound Tigers isn't mentioned, as they went to the Calder Cup finals that season

[@MrZachtheKingsfan]

You hit the nail on the head when it comes to goalies. When a skater slumps, there are other roles outside of scoring goals they can excel and still be a key factor to their team. When a goalie slumps, there isn’t really anything you can do. You have one job as a goalie (a very hard job I might add), and if you can’t do that job, there really isn’t a backup role you can take.

[@deansmith6593]

Mike Milbury had such entertainment value wish he would get hired as an NHL gm again (as long as it is not the team I route for of course).

[@reasonablerage4370]

root*

[@ronniejamesdio4468]

Greatest Jersey in NHL history

[@ScaryRevenant]

I can remember his draft year he was very highly touted. This was when Detroit, Dallas and Colorado dominated the league. I figured one of those teams would have him when he was a veteran until the islanders gave him that monster contract lol

[@jo-um7yf]

The only reason Milbury picked him so high was that he was a Boston guy like him. This is yet another example of why Mike Milbury was THE WORST GM IN THE HISTORY OF ANY PROFESSIONAL SPORT...EVER!!!! DiPietro wasn't a bad goalie, but NO WAY he was worthy of a #1 selection.

[@jordanhoughton1948]

Worse than Matt Millen with the Detroit Lions?

[@sip5257]

Steve Somers on WFAN New York City always called Rick DiPietro Mr. Olympic!!! Always remember that

[@madpandahat]

Good ole Rickety. Didn't know about the cap difference in that way it sort of makes sense. Regardless I think even if we're healthy he'd never beat out Lueongo. Thanks for the isles attention lately Shannon :)

[@elwizschold]

It's not a cap hit, but they still pay him that 1.5 until 2029. It was a compliance buyout

[@donaldpaluga]

Hockey's version of Bobby Bonilla

[@andrewhogan6533]

This kid was going to be very good. He played during some of the down years for the Isles, but he was a competitor and was getting better. He gets tons of flack for being number 1 overall and getting a huge contract. It’s similar to Dan Blackburn who also had his career derailed early. Everybody was looking for the next Brodeur drafting goalies in the first round all the time. Another what could have been.

[@richardferguson6893]

That injury to Blackburn's shoulder was so unfortunate. Really think he would have had a great career.

[@tjisbatman]

The coolest thing about DP is that the islanders are still paying him 1.5 million until 2028

[@garybass4029]

Wow alot of injuries! At least he still sort of stayed with hockey finding broadcasting for his career. Great video! 👏 👏

[@JarradBruessel32]

I had a gotten an ITECH brand stick with the DiPietro curve when in high school. It didn't even last 10 minutes into the first practice and it broke in half lmfao

[@NolanEgbert]

What ended DiPietro's career wasn't the all-star injury. In his own words, he was able to bounce back from the hip injuries. It was a botched knee surgery around 2008-09 that did him in. The doctors went with a procedure that wasn't what a goaltender should do and he was never able to move correctly or with any confidence ever again

[@lmtman6199]

An absolute legend in the eyes of all Ranger fans

[@knessing7681]

the dude and his family are set for Life.

[@wonderingwayne3480]

Do you have a career video for Michel Plasse? The first goalie taken #1... and if you want to get technical he went #1 twice.

[@mrkane7890]

baseball now has these super-long contracts, for much of the same reason (although in MLB it's a luxury tax not a hard cap)

[@nowaybruh145]

That contract was a Garth Snow deal. They were besties Rick's first years in the show. The owner Charles Wang (I think) loved Ricky. LOVED. So when Rick's best friend got promoted to GM, this mega deal was essentially a buddy buddy deal between the three of them. Source: I was hanging out with Rick in Winthrop that summer.

[@Outta-hz1ej]

Rick Dipietro in a way, was just, like my islanders.

[@JK_35]

Just watched Big shot on Disney plus about spans trying to buy the New York Islanders, such a crazy story

[@landonlc4]

one of the only NHL goalies to rep ITECH goaltender equipment as their mainstay.

[@JarradBruessel32]

I had a gotten an ITECH brand stick with the DiPietro curve when in high school. It didn't even last 10 minutes into the first practice and it broke in half lmfao

[@slurmsmckenzie5828]

I was at the game Brent Johnson hit him with the one punch man. People were going abaolutely bananas man. Wild memory

[@dnasty312]

Other careers with long contracts you should look at: *•Mike Richards* *•Shea Weber* *•Jeff Carter* (when he retires)

[@Ratzy1614]

Crazy the Islanders could have had Luongo, Redden, Chara, Heatley/Gaborik as the stars of their team in the 2000s

[@nintendoconvert4045]

Pronger, Carter, Richards - the Flyers used these long term deals to lower the cap hit a lot around this time.

[@lrba5524]

my personal hero

[@lancemilliken9078]

This contract was a true albatross

[@doh-nc8ku]

Wow I knew DiPietro was a goalie for the islanders from his radio show, but FIRST OVERALL? GOALIE? Damn! Injuries derailed his career unfortunately I learned too. Secured that bag tho 😂

[@qualityherbsonly]

You should make a video, if you haven’t already, about all the long contracts that were signed around this time.

[@rmd1477]

very interesting!

[@adamg7984]

Man, the saddest thing about DiPietro's fight was he was just having some fun. Had a big old smile on his face, just wanted to say he had a fight in his career, you could tell that's what he was thinking. Now, Johnson looked a lot more serious but I really don't think Johnson meant to hurt DiPietro, but he gave one punch, hit DiPietro right on the button and broke his jaw. I feel so bad re-watching that as I saw it live. I'm a Pens fan and happened to watch that game when it devolved into a line brawl and was cheering like crazy when they fought but I was a dumb kid. Now I just can't believe DiPietro, a guy who had injury issues his whole career, had his jaw cracked from one stupid punch in garbage time of a regular season game. Just how unlucky was the guy.

[@IceNinja2007]

Fun fact the helmet that he wore was Chris osgood's old helmet.

[@suburbanindie]

He only did that for a short time in 2010 I wanna say until Brian Rolston rang a clapper off his noggin and gave him another concussion.

[@GoHabsGo-db7cb]

1-4 with a 908 he must have stood on his head!

[@Nud182]

wow, imagine having luongo and either heatley or gaborik. Def coulda built a great team around that foundation. unfortunately , milbury.

[@mikefalanga437]

I remember that draft well, I wanted Gaborik all the way, I wasn't really crazy about Loungo either ,but i figured that if the isles could find a decent shooter for a change ,that they'd pick up up a few more wins per season and maybe even trade Loungo and grab a top 5 goalie of the time!

[@jeffa.7618]

D P, bom-bom, D P!!! Loved my Devils crushing him back in the day, but he was pretty good. Obviously that 15 year contract was absurd, and what he'll be remembered for, but he was pretty good before the knee issues.

[@NYM27]

N J 🤡

[@jeffa.7618]

@@NYM27 I watched my team win three cups live, and I will always proudly support for them. (Don't ever pity me or NJD). They certainly weren't 🤡 in DiPietro's heyday, that's for sure.

[@AyeThatsHandsomePete]

Oh man, Glass Jaw DiPietro.

[@Spidey1015]

Watched him play his final NCAA game in the NCAA tournament with BU. All time classic, the game went 4 overtimes against St. Lawrence (BU would lose 3-2), crazy goaltending duel against SLU's Derek Gustafson who had an outstanding freshman year, left school after that season and signed with Minnesota. Both goaltenders racked up around 70-80 saves if I remember correctly. Gustafson ended up barely having a cup of coffee during his career.

[@brianshaughnessy4020]

Yes, DiPietro made a tournament-record 77 saves in that game, which was the longest game in NCAA tourney history until Minnesota Duluth and North Dakota played five overtimes in 2021.

[@zachmontminy]

Martin Havlat career video!

[@brettscheuermann7335]

You just mentioned him, dwayne roloson career vid?

[@nathanjohnson2382]

Something about New York teams that wear Orange and blue with stupid contracts. July 1st Goated Bobby Bonilla and Rick Dipietro day

[@JarradBruessel32]

Glad I'm not the only one to notice that lol

[@swedreamhack5308]

It's easy to look back in hindsight and laugh at this but to be fair, it's not Dipietro's fault somebody was willing to throw those millions at him. A 15 year contract is insane and especially for a goaltender that had one good year, the term didn't make sense back then either. One of the worst of Islanders many strange decisions in the early to mid 00's.

[@RoscoMontana21]

I like to think Mike Millbury has a tally sheet, and every day he marks off another day of paying Rick.

[@JohnpaulDejoria666]

Queens is technically on the land mass that also includes Long Island. Looking back at the Bonilla deal, GM’s on that piece of land make the dumbest contracts

[@shanielcabral]

Now Mike and Rick are both on tv

[@yoholmes273]

The epitome of how NOT to draft and how NOT to write a contract. The poster boy for 1990s Islander futility.

[@suburbanindie]

That 09-10 season was fun with Dwayne Roloson in net; Matt Moulson, rookie Tavares, Okposo, James Wisniewski, Mark Streit... there were lean years then but something felt fun about it. You could feel a shift in the culture a little bit

[@Greenfrom3]

As an Oilers fan I love me some Dwayne Roloson. He was a hell of a goalie.

[@golsonmoldon9455]

15 out of the required 16 PO games won that yr with him. 1 short, hell of a run..

[@suburbanindie]

@@golsonmoldon9455 Dude would stand on his head. Excellent goalie, very underrated and almost forgotten

[@golsonmoldon9455]

@@suburbanindie for sure, that Mac T coached squad had beauty run that yr. Emphasized, the, a hot goalie can win you the cup, phrase. Almost.

[@JarradBruessel32]

@@Greenfrom3 I met roloson in 2004 I believe. He was so nice. I miss him.

[@1bert719]

Solid when he was healthy behind a so so Isles defence. In NHL 2003 he was deadly poor high blocker, not sure how accurate that was throughout his career. 😋

[@faunbudweis]

the one fight against Johnson :)

[@JarradBruessel32]

It's hysterical that at one time I had purchased an Itech stick that was a dipietro curve and it broke in the very first practice I used it 🤣 😂

[@Tykoon22]

Do you think the maximum contract length in the NHL Will be reduced again at some point? Right now, we have the 7 and 8 year max deals, But do you think the NHL Will try to bring that down a bit more, maybe they try to mirror the NBA with 4 and 5 year max contracts, or maybe somewhere in between like 5 and 6 or 6 and 7? I know all of that has to be negotiated through the CBA, so I guess i’m just wondering if the league has an ideal maximum contract length they would like to see implemented, how low they would want to go and how far would the players let them?

[@MrReelio3]

DiPietro is one of the guys I just felt bad for. Played for a horrendous team, but clearly loved playing hockey and playing for the Islanders. The freak injuries would just not give this guy a break, between the knees, the hips, the broken jaws, etc. I guess he gets his money in the end, but he's the kind of guy that would've made a good ambassador for the Isles if he was around over the long term.

[@MrOctober44]

Horrendous teams? They made the playoffs four times in five years from 01-07. Not great teams but horrendous is a ridiculous statement.

[@jdeighan]

I forget which game whether it was nhl 2001 or 2002, I don't know but in the career mode by the 3rd or 4th season DiPietro would be at least 92 overall rating. Every time. And I think he starts out as a 58 or 68.

[@connor_weggy]

It’s funny that he was the first player I ever liked when I was 4 years old

[@andrewchevrier]

I remember watching the All Star game, and the breakaway challenge where DiPietro injured his knee and missed the rest of the season.

[@iampete8692]

"Well, I traded you and Oleg for Jokinen and Luongo" "Umm, what was that? Who? Wha? uh... Wow, I don't blame you at all. Good luck, Brian"

[@thekreal8703]

Big Val staying in Colorado!!

[@paulmacdonald9908]

I remember the day after the deal was signed and a co-worker said to me knowing I a was an Islanders fan, "I have a bad feeling about this deal."

[@XaviRonaldo0]

He definitely had the talent

[@taskdon769]

And he is still getting paid by Islanders for 1.5M a year until 2028, he is like Bobby Bonilla of NHL. Don't know if you have done Kovalchuk's career review already but his contract is even more funnier considering that two teams were ended up taking cap penalties concurrently at the same time for 2 years (and the Devils are still taking the cap hit until 2025).

[@Mayor_Of_Eureka17]

My man had hands tho ..

[@klompsauce]

Oh!

[@isaacwest276]

I don't know if he was 1st Overall goalie, but he had the talent of being a 1st round goalie. He got ruined by one of if not the worst managed moments in NHL history, plus a terrible injury. Don't feel bad for him though, as you're watching this video you can understanding that the Islanders are still quite literally paying DiPietro for how poor the situations they through him in were.

[@chadisnotachad]

He's the reason the Islanders used to be my second team.

[@Cinerary]

You mean Rick DiPieGOAT

[@kevinzielinski9568]

The Bobby Benia of the NHL

[@kcjc]

Coincidentally I just got a card of him in the mail today

[@literallywho4197]

Had he stayed healthy, $4.5 million would've been a steal in the cap era.

[@LateCloser]

Yeah, it was the era of circumventing the cap but I think everyone knew that contract was going to backfire.

[@BradyBanta]

No audio shannon

[@rockybalboa1847]

How come my 7 year old tablet never has any audio issues ... just wondering

[@Bsweds32]

He's like Bobby Bonilla with that contract.

[@bryannewcombe858]

DiPietro IS the Bobby Bonilla of hockey when it comes to contracts.

[@m00rtin4]

Wth i was almost certain u did a vid of him already.

[@midimusicforever]

Me when I clicked: "Why is this video 11 minutes long, rather than 2?

[@AAbram-yt9de]

The Bobby Bonilla of the NHL

[@chickenfkeryay]

Dipietro was q good goalie. That contract isnt an albatross as it didnt affect the isles cap situation or force them to salary dump players.

[@wattsup4800]

Bad contract but after seeing this not terribly bad. Worst decision was trading luongo. I’ve met DP several times and is a great guy.

[@jamesgentry13]

What career?

[@christhornycroft3686]

Does this still affect their cap? They should have been able to put him on LTIR. I guess the owner would still be on the hook for the money, but in terms of being able to put together a roster, this shouldn’t affect anything, should it?

[@rhaspados666]

If they didn't buy him out they could but since they bought him out they still count that 1.5 mil against the cap

[@kylejohansen689]

They still pay him but it's not against the cap.

[@NolanEgbert]

@@rhaspados666 It was a compliance buy out after the 2013 lockout, so he does not count against the cap

[@JarradBruessel32]

@@rhaspados666 its not. It was a compliance buyout

[@janellemaynait]

Hockey's Bobby Bonilla

[@dawnsempire8510]

wait a sec: i know people bring up DiPietro because of the contract length, but i thought he actually had the same salary for all 15 years, so he's not really an example of the back-diving contracts, right?

[@joe09131]

As a long time Islanders fan this whole fiasco still haunts me to this day... I remember watching the few games Luongo played I can remember thinking... this guy has shown flashes, he has a chance at being big time, as bad as the Islanders were. Of course no one new that Luongo would become a star goalie at the time but there were flashes. I remember reading about Depietro in hockey magazines and all the hype. I'm sorry but I just didn't see what all the hype was about. I just didn't see how he was like the next "superstar goalie". Heck, I even thought Eric Fichaud had a chance to be big time until he started getting injured. Man this still hurts lol.

[@MrOctober44]

I definitely remember thinking that Luongo was going to be a star. Yeah, Fichaud was another one done in by injuries. Also a first round pick. I like Dipi, it's a shame what if legacy is. Having said that, I never understood what Millbury saw him. Solid goalie but never seemed like he was going to be an elite goalie.