The Theoretical Soundness of the Rick DiPietro Contract

The Consequences of its Failure on the Goalie Market

Everyone knows the story: Rick DiPietro signs a $65.5 million dollar, 15 year contract with the New York Islanders in 2006-07, gets frequently injured causing his play to diminish to the point of needing to retire, and remains on the Islanders’ payroll to this day — like the hockey equivalent of Bobby Bonilla. This is the story we tell each other and we have a good laugh at the expense of the late 00s Islanders.

Rick DiPietro (pictured) was oft-injured and perceived as overpaid. But was his contract a good idea at the time of signing?

But the strangest thing about this deal is that it actually made sense. Looking at DiPietro’s results, it’s not immediately obvious why. He wasn’t spectacular before the contract, and he didn’t see the full contract through. But sandwiched in the middle of his three 60-game seasons was a 2006-07 season that not only suggested his pay grade, but also his draft pedigree as first overall in the 2000 NHL draft.

But just because it didn’t pan out, or makes sense when looking at DiPietro’s stat line doesn’t mean it was an unsound move theoretically.

Pre-Payday Career (2000-2006)

Rick DiPietro was a highly anticipated prospect going into the 2000 draft. His performance on the USNDPT and later Boston University was impressive. He had tools like exceptional lateral movement and puck handling ability. This is what a large part of what motivated his selection as the first overall pick that year over scoring wingers Dany Heatley and Mariàn Gàborìk.

Was this the right selection? Perhaps not. The Islanders famously already had their 1997 4th overall pick, Roberto Luongo, in the NHL. He was doing alright too: 100 GA%- in 24 GP isn’t bad at all for a 20-year old on a bad Islanders team. But the Islanders wanted to reverse their fortunes and quickly. So they traded Luongo and an underperforming Centre Olli Jokinen to the Florida Panthers for forwards Oleg Kvasha and Mark Parrish: the deal was 2 for 2.

Kvasha and, especially, Parrish weren’t bad for the Islanders in 2000-01. Jokinen, on the other hand, was horrible for the Panthers, posting -0.3 point shares in his first season in Florida. Luongo, for his part, excelled in net. In 47 games played, he had an 83 GA%-, a 21.9 GSAA, and a 10.2 GPS, which dwarfs Parrish and Kvasha’s combined 3.3 Point shares. On point share aggregate, that’d be 9.9 point shares for the Panthers and 3.3 Point shares for the Islanders.

Looking at the trade, it’s easy to criticize — even with Jokinen theoretically being worth negative value in his first season — but it’s actually worse than you already thought.

Here’s the thing: Luongo was traded because the Islanders wanted DiPietro. They acquired scoring wingers in exchange. The next two picks after DiPietro were all-star scoring wingers. So, because the trade is so tied to the first overall draft pick, we can think of the Luongo trade like this:

New York Islanders acquire:

• Oleg Kvasha (W)

• Mark Parrish (W)

• Rick DiPietro (G)

New York Islanders lose:

• Roberto Luongo (G)

• Olli Jokinen (C)

• Dany Heatley (W) xOR¹ Mariàn Gàborìk (W)

We’re going to assume that Kvasha and Jokinen effectively even out through 2003-04 — even though between 2000/2001-2003/2004 Olli Jokinen had a PS of 14.5 to Kvasha’s 12.4 Point Shares . I’m actually going to give Milbury a mulligan on that part of the deal, because Jokinen was struggling in his first few years.

So that leaves us with the following question to get to the crux of judging this trade: was the (perceived or projected) talent gap between DiPietro and Luongo greater than the (perceived or projected) talent gap between Heatley/Gàborìk and Parrish? I.e.

(DiPietro − Luongo) > ([Heatley xOR Gàborìk] − Parrish)

And the answer is no. Even at the time, I don’t think that’d be the case. Luongo was in the NHL, playing at a league-average level, and only 2 years DiPietro’s senior. But that’s not really DiPietro’s fault, and a charitable interpretation of the facts speaks to DiPietro having a truly enormous ceiling.

In what one might call “foreshadowing”, DiPietro suffered a groin injury in training camp before the 2000-01 season, causing him to start the season in AHL affiliate Bridgeport —the unsettling implication being that the Islanders were otherwise going to start him in the NHL right away. DiPietro then made his NHL debut in January 2001 against the Buffalo Sabres.

DiPietro’s first 3 games were in keeping with his pedigree: 3 games, > 55 minutes and >.930 SV% in each— and all of them were loses! But, in his 4th game, he played more in line with what one would expect a 19-year-old goalie in the NHL would be. He bounced back, though, allowing no goals in his next appearance versus Montreal… in which he played only 3 seconds. He bounced back for real against Ottawa and Edmonton, stopping 55 out of 60 shots, for a save percentage of .917 over those two games. A respectable .903 SV% loss to Vancouver was the penultimate game in which he recorded a save percentage at or above league-average. He registered a .858 SV% over his final 12 games that season, having started at .910 over his first 8² games. This is what happens when you throw a 19-year-old goalie into the NHL: they don’t succeed, generally. His stats (20 GP, 126 GA%−, −13.2 GSAA) attest to this. His reappearance for ten games in 2002-03 didn’t go too much better (GP 10, 117 GA%−, −4.1 GSAA). But his next two seasons, where he was the starter, did good rather well.

• 2003-04: 50 GP, 100 GA%−, 0.3 GSAA

• 2005-06: 63 GP, 101 GA%−, −2.6 GSAA

Looking back at the seasons preceding that infamous contract, his age 19-25 seasons, his play wasn’t very good. He played a total of 143 NHL games and posted a 107 GA%−, −23.8 GSAA, and 21.3 GPS. Now, most of this was due to his first two seasons (30 GP, 125 GA%−, −18.4 GSAA, 2.8 GPS), which were truly awful stuff. Otherwise, he was barely below average — 113 GP, 102 GA%−, −4.4 GSAA, 18.4 GPS — in his 3rd and 4th seasons.

So here’s this goalie that your organization bet heavily on — selected 1st overall, trading away a generational goalie in the process — is there the possibility that some of that was sunk-cost fallacy? Absolutely! But even though DiPietro didn’t have a Luongo-esque career coming into 2006-07, he still had the tools that had made him a top pick and top prospect.

It’s also important to note that Garth Snow, the Islanders’ recently retired backup goalie and newly hired GM, had been hired by the team’s new ownership the off-season the contract was offered. But Garth Snow had been DiPietro’s goalie partner and seen his progress up-close. One might assume that he was pretty big on Ricky D’s tools as well.

This was the longest contract signed in the salary cap era up to that point and only nearly surpassed by Ilya Kovalchuk’s absolute monster of a 17-year contract offer by Devils, which was kiboshed because it was obvious cap circumvention. These contracts likely lead to the 8-year term limit on UFA contracts in the 2013 CBA agreement.

But here’s the $65.5 Million question: was it a good idea?

In a lot of ways — even without hindsight — no! DiPietro was just below average in two seasons of 50+ games before and after the lockout. Given DiPietro’s age at the time of the lockout, a bigger jump in his play could have been anticipated. But the weird thing is, DiPietro didn’t play in 2004-05. I’m not fully sure why. Ryan Miller, a goalie one year DiPietro’s senior, played 2004-05 for the Rochester Americans and broke out the next season with Buffalo.

But all the same, in September 2006, DiPietro signed the now-infamous 15-year $65.5 million contract.

What the Islanders got right

1. Term — Yes, 15 years is a long time and sometimes goalies breakdown, but this allows the Islanders to accept a lot of risk to pay DiPietro less overall on average. Juuse Saros’s contract signed just this past off-season carried a cap-hit of $7.74 Million AAV, but he’s getting paid around $11M this season and taking a pay-cut towards the end of the contract. It’s the same principle.

2. Cap % — So $65.5 Million works out to a 15x4.5m contract. Given the salary cap of the time (44m), that's 10.2% of the salary cap. For context that's about 8.6m in today's NHL since the cap has literally doubled. That seems like a lot of money — and it is: Jeremy Swayman signed for about that much cap percentage last off-season. But we need to consider one fact about that 10.2%: that’s only relative to the year that contract was signed. So long as the cap continued to rise, which it generally did, DiPietro’s cap hit (as a percentage) would “decay” over time. Now, I don’t know if Snow could have foreseen the cap rising as much as it has, but it’s certainly not a bad inference.

3. Anticipating a peak — This is what no one learned from the DiPietro contract and what teams continue to get wrong about goalie contracts. The biggest success of the DiPietro’s contract was anticipating his play as an elite goalie. Because for one season — 2006-07, the year after his contract was signed — DiPietro was elite. His stat line was 63 GP, 86 GA%−, 25.7 GSAA. The Islanders didn’t wait for DiPietro to produce like that to give him his bag. They bet on a talented goalie for the talent, instead of waiting for results. If we compare this to the Swayman situation from this summer, this is the part that Boston didn’t get. The cap% was similar and the term was comparable, but Swayman had to basically threaten a hold-out to get it. If Boston had understood the value — both from his tools and his results — Swayman represented, they probably would have tried harder to get a deal done sooner and not have pointed to things like Swayman’s playoff performance (which has actually been fine, by the way) as a way to argue down his contract. Instead, Boston got caught in an impasse, prevented Swayman from attending training camp, and undermined the relationship between their front office and their 2nd-to-3rd-most impactful player. The Bruins front office should have known Swayman’s skill set was legit and paid him accordingly.

2006-07

Let’s contextualize DiPietro’s 2006-07 on the macro. In the salary-cap era (2005-06 — present), there have been 25 individual goalies seasons where a goalie has appeared in 60 or more games with a GA%− of 86 or less, and only 3 goalies have done it twice: Connor Hellebuyck (2022-23, 2023-24), Roberto Luongo³ (2006-07, 2010-11), and Tomáš Vokoun⁴ (2005-06, 2009-10). That’s elite play, no matter how you cut it. It’s a strong volume and a strong rate of puck-stopping.

To be clear, this kind of season is special in the Salary Cap NHL, but it’s not tantamount to greatness by itself. Darcy Kuemper and Alexandar Georgiev are two goalies who featured on the above list quite recently. They did so as many times as Carey Price, whose 78 GA%− is the lowest on the list. And presumptive-Hall-of-Famer, Vezina-winner, and fellow first-overall pick Marc-André Fleury never had a season like that. But given that (1) this Islanders team was fringe-playoff even with their Free Agent and trade-deadline acquisitions and DiPietro’s ascendancy, (2) DiPietro’s pedigree and tools, and (3) the workload he had, we can safely say this was a legitimate breakout season for DiPietro.

It was not all dominance, however. DiPietro posted an 0.897 SV% over 7 games in October, but rebounded in November and December posting SV%’s of 0.931 in 10 games and 0.923 in 12 games, respectively. January had some hiccups with a 0.889 SV% in 11 games played, but DiPietro bounced back again with 12 games of 0.926 SV% in February. He ended off with 10 games of 0.939 SV%, but suffered a concussion after a collision with Montréal forward Steve Begin in the first period of a game on March 13th. He was back a week later for a game against the Lightning, but was re-concussed in a game against the Rangers on the 25th. Famously, Wade Dubielewicz had to come in and carry the Islanders to the playoffs.

DiPietro’s playoff appearances that year came in games 2-5 of a series against the “Best Team without a Hall of Famer” Buffalo Sabres. He won his first game back (game 2), but lost the next 3. Regular readers will no my trepidation for judging playoff performance, but given the sheer offensive firepower of these Sabres, I think he fared fairly well.

Following the game 5 loss and end of their season, DiPietro went under the knife for arthroscopic surgery to repair his left hip. Yikes.

This is where DiPietro becomes infamous. Keep in mind the two types of injuries that DiPietro suffered throughout his career were lower-body (knee and hip) and concussions. But these kinds of injuries are among the worst a goalie can suffer. Craig Anderson’s infamous hand injury, which occurred while he was cutting frozen chicken, didn’t have much of a lasting effect on his career. But even hip and knee surgeries — especially over a decade after DiPietro’s infamous string of bad injury luck — can have different results for different goalies. Antii Raanta had a career plagued by injuries, but was otherwise generally good when he was healthy. It seems that only in the last two seasons was it clear that the many surgeries were perhaps impeding his ability to play at the NHL level.

But DiPietro was among the first cohort of modern butterfly goalies coming into the league. That generation also produced the likes of Roberto Luongo, Pascale Leclair, Kari Lehtinen, and Marc-André Fleury. These were all first-round pick goalies who entered the league fairly quickly and were expected to carry heavy workloads early in their careers. Only Leclair and DiPietro were truly “wrecked”, but Lehtinen also had a lot of injuries early in his career.

But this arthroscopic surgery becomes important the very next season — which would be his last “full” season.

2007-08

His 2007-08 —especially by comparison— was pretty bad: 63 GS, .902 SV% 108 GA%−, −12.4 GSAA. But crucial to understand is that Rick DiPietro tweaked his hip — same one he had surgery on — during the 2008 NHL skills competition. If we look at his 44 games pre-all-star break, he was posting a .911 SV% or approximately 98 GA%− — although in his last 3 starts going into the break, he hadn’t recorded a quality start (a start in which the goalie records a SV% of league average or higher when facing 20 or more shots or a .885 SV% or higher when facing fewer than 20). This streak continued after the all-star break for a further 7 games until finally he got one on February 16th in a bizarre 9-save, 1-goal-against game against Atlanta. He then consecutively recorded an additional 3 quality starts — including a shutout in the last of this stretch — and then not a one for the rest of the season, which ended for him on March 15th after the Islanders were eliminated from playoff contention.

So, if I’m trying to analyze DiPietro’s 2007-08 as being pretty alright/average until being derailed by playing through injury, there are two things that are inconvenient to that view.

1. Why did his floundering begin before his All-star game injury?

2. Why did he have a 4-game stretch of terrific play in the middle of his post-All-star game portion of his season.

Well, I can’t say for sure, but let’s consider a few things: (1) DiPietro started 63 games before March 15th. How many more starts would he have gotten had he not been shut down? He already had started 86% of the Islanders’ games, but would have started 71 had that pace been maintained through the full 82-game season. It’s also worth noting that DiPietro started 44/50 of the Islanders pre-All-Star games — that’s 88% of all the starts! Consider that he just came back from surgery over the summer, then gets thrown this huge workload. It’s understandable that he would regress. but even still, while his October started off weak (0.890 SV% in 8 games played), he had another great November (0.923 SV% in 14 games) December (0.908 SV% in 11 games) and January (0.910 SV% in 12 games) were average, but February (0.889 SV% in 13 games), on the whole, was dreadful. March was even worse (0.870 SV% in 5 games). So, it actually could be more of a workload issue aggravating an injury or just downward trend coincidental with hip tweaking at the 2008 ASG.

(2), Injuries are not experienced linearly. It’s not unrealistic to imagine that there were days where DiPietro felt better and days where he felt worse. It’s furthermore, realistic to imagine that he was more likely to feel worse the more he tried to play through his injury.

Conclusion

After the 2007-08 season, Rick DiPietro only played 45 more NHL games retiring at the end of the 2012-13 season. The narrative I present here is as follows: his many hip and knee injuries sapped the speed and mobility that had made him such a raw talent, leading to his NHL exit. The concussions, however, are likely what prevented him from continuing in pro hockey altogether.

In hindsight, the Islanders certainly regretted the DiPietro contract — as they should have! 15 years is a long time to commit to a goalie, and that carries risk, but had the Islanders been able to build a contender — or even a playoff team — around a healthy and consistent DiPietro for the early-2010s, it’d have been worth it for creating the window. It’s important to realize that the term allowed the Islanders — not an overly attractive destination for Free Agents — to ensure they had their guy without risking having to pay him even more for an extension. They were paying more to by-pass free agency.

Who Could He Have Been?

With a tool set like DiPietro’s, what could he have been had his career played out differently. I think had he been shut down after the All-Star break in 2007-08, his career could have been similar to a post-Vezina Miikka Kiprusoff. That was his floor. I’m not kidding. Had Rick DiPietro not become chronically injured, his floor would have been Miikka Kiprusoff. Something in line with Kiprusoff’s 2007-08 (76 GS, 103 GA%−) was certainly possible for DiPietro to maintain with the ever-present possibility of approaching his own 2006-07 high-water mark.

Measuring by Point Shares, in order to “be worth” his cap hit (which well measure by cap percentage), Rick DiPietro would have had to accumulate about 10 goalie Point Shares⁵. That’s very doable for a goalie playing on a team intent on playing their starter into the ground, like the Islanders were.

But if we “intervene” earlier, say, and keep him in the NCAA for a year or two longer, does that extend his career? Likely. He was in the NHL at a young age, albeit not permanently, but not having more seasons of a more practice/training-oriented schedule could have been detrimental to his development. The one-year-older Ryan Miller, who was in college hockey until age 22, was able to successfully become the type of workhorse goalie the Islanders wanted DiPietro to be in roughly the same time frame. Neither broke out until after the lockout, despite DiPietro having more games played than Miller.

But then again, maybe that wasn’t the right choice for DiPietro. Fellow first-overall-er Marc-André Fleury has had a long and storied career and made the jump to the NHL around the same age on arguably a worse team. It’s hard to say for sure.

Goalie Contracts

I could have gone into more detail in this article about comparative contracts in the cap era, but given the narratives surrounding DiPietro, I chose not to and focus on him instead. I will elaborate on this in a future article, however, using Henrik Lundqvist’s functionally identical final two contracts as — what I believe should be — the models of the goalie market: indeed, their term lengths of 7 and 8 years make them replicable under a post-2013 CBA.

In the off-season, I wrote about the Bruins dawdling in negotiations with Jeremy Swayman. Had the CBA allowed it, I’d have advocated for term length longer than 8 years, similar to Roberto Luongo’s⁶ final contract. But the main point is that the Bruins did do well to anticipate peak Swayman rather than react to it. Even still, despite the organizational… uh, “reluctance” to hand out $64 million to a young, talented goalie, the Bruins will benefit for years to come — even if the results aren’t fully consistent year-over-year.

And overall, that’s what the Islanders got right with DiPietro. They knew his talent level and knew what he could become: elite. And he was, for a season, just that: elite. But cascading injuries to his head and lower body and trying to play through many of those injuries prevented him from having a longer career, and quieting the narratives surrounding his theoretically sound contract.

1. The “or” is exclusive, meaning it must be either Heatley or Gaborik

2. Including his 3-second, 0-shot performance against Montreal

3. Which he already did in 2003-04, as I covered in my “Greatest Vezina Snub in NHL History” article.

4. Wow! That’s some pretty good goaltending! I wonder if a very smart and handsome substack-writer has argued that this Vokoun guy should be in the hall of fame.

5. For sake of argument, we’ll assume a team spending to the cap should expect at least 100 points per season. I will expand on this idea in a later article.

6. I want to make a formal apology to Rick DiPietro for all these Luongo comparisons. He’s probably been hearing them for the last 25 years.