One of the most frustrating aspects of rooting for the New York Knicks lies in knowing that owner James Dolan—with billions in media money behind him—has routinely squandered his franchise’s almost-unparalleled fortune.

And we’re not just talking about the monetary kind, either.

When Dolan assumed control of the Knicks, he wasn’t just inheriting a professional sports team situated in the heart of the world’s chief media market; he was assuming the role of caretaker for a legacy built on loyalty and long-standing basketball tradition.

And yet, year after year, Knicks management finds new and creative ways of financially forsaking that very trust—and pilfering Dolan’s own war chest in the process.

Because the NBA operates under a league-wide salary cap, conventional wisdom would suggest that owners and general managers would be more careful about the length and size of contracts than, say, their Major League Baseball counterparts.

Defining the Terms

Not Guitar Jimmy.

So join us as we highlight the 15 most ridiculous, onerous and downright offensive contracts of the James Dolan era, together with what I—Jim Cavan—feel they should have been paid.

Admittedly, that last part amounted to [quasi-educated] guesswork, and is really just the tip of the mismanagement iceberg. Indeed, for every dollar spent on terrible player contracts, we can probably dig up at least 25 cents wasted on fired coaches, executives, general inefficiencies, and the like. 

Repeat: This is not an exact science.

Obviously, there are considerations that go beyond what the receiving team believes a given player is worth in the most literal sense—expiring contracts, overall financial flexibility, etc. Still, we can assume these things even out on both ends, which is why we’re taking the money these guys made with the Knicks at face value.

Additionally, while a lot of these deals were made under the old CBA(s), we’re evaluating the contracts by what they might look like today.

As such, we’ll be using the following, admittedly general denominations: “veterans minimum” (denotes anything at or around $1 million per year), “mid-level” (here, $2-4 million), “starter” (in the $5 to $8 million range), “near-max” ($9 to $12 million) and “max” (anything above that).

One final programming note: For players acquired via trade, we’re only counting their salary with the Knicks—either before they were traded again, waived outright or entered free agency.

By the end, we’ll have a general estimate of just how much money the Knicks’ renegade regime has piled up on the Garden floor, doused in kerosene and set on fire. 

Spoiler: It’s enough to buy islands—plural.

Tier 1: 'That Was Pretty Dumb'

Clarence Weatherspoon (free agent, 2001)

What he got paid: 2 years, $9.5 million

What he was really worth: 2 years, $5 million (mid-level)

Dolan Dollars wasted: $4.5 million

Howard Eisley (trade, 2001)

What he got paid: 3 years, $18.8 million

What he was really worth: 2 years, $6 million (mid-level)

Dolan Dollars wasted: $12.8 million

Keith Van Horn (trade, 2001)

What he got paid: 1 year, $13.3 million

What he was really worth: 1 year, $8 million (starter)

Dolan Dollars wasted: $5.3 million

Steve Francis (trade, 2006)

What he got paid: 1 year, $15 million

What he was really worth: 2 years, $10 million (starter)

Dolan Dollars wasted: $5 million

Patrick Ewing (free agent, 1997)

What he got paid: 4 years, $60 million

What he should’ve got paid: 4 years, $48 million (near-max)

Dolan Dollars wasted: $12 million

Including Ewing here was tough. He is, after all, an all-time Knicks legend. Still, if the Knicks hadn't signed him to such an onerous tender, maybe his departure wouldn't have been so unceremonious. Something to consider, anyway.

Tier 2: 'That Was Really Dumb'

Shandon Anderson (trade, 2001)

What he got paid: 4 years, $25.6 million

What he was really worth: 2 years, $6 million (mid-level)

Dolan Dollars wasted: $19.6 million

Penny Hardaway (trade, 2004)

What he got paid: 2 years, $30.3 million

What he was really worth: 2 years, $8 million (mid-level)

Dolan Dollars wasted: $22.3 million

Quentin Richardson (trade, 2005)

What he got paid: 4 yeas, $31 million

What he was really worth: 3 years, $12 million (mid-level)

Dolan Dollars wasted: $19 million

Travis Knight (trade, 2000)

What he got paid: 4 years, $15 million

What he was really worth: 2 years, $2 million (veterans minimum)

Dolan Dollars wasted: $13 million

Jerome James (free agent, 2005)

What he got paid: 3 years, $16 million

What he was really worth: 2 years, $1.5 million (veterans minimum)

Dolan Dollars wasted: $14.5 million

While not the kind of moves that cripple a franchise long-term, if there are at least five incendiary contracts beyond this, how much worse can it get?

Buckle up.

Tier 3: 'Straight-Up, 100 Percent Money Apocalypse'

Stephon Marbury (trade, 2004)

What he got paid: 5 years, $90 million

What he was really worth: 4 years, $36 million (near-max)

Dolan Dollars wasted: $54 million

Larry Johnson (trade, 1996)

What he got paid: 7 years, $67 million

What he was really worth: 4 years, $32 million (starter)

Dolan Dollars wasted: $35 million

Eddy Curry (trade, 2007)

What he got paid: 5 years, $45 million

What he was really worth: 3 years, $20 million (starter)

Dolan Dollars wasted: $25 million

Allan Houston (free agent, 2001)

What he got paid: 6 years, $100 million

What he was really worth: 4 years, $56 million (max)

Dolan Dollars wasted: $44 million

Amar’e Stoudemire (free agent, 2010)

What he got paid: 5 years, $100 million

What he was really worth: 4 years, $64 million (max)

Dolan Dollars wasted: $36 million

Quick note on Johnson: Because Dolan hadn't yet assumed full control of the Knicks in 1996, it's difficult to say how much sway, if any, he had on the LJ deal. Even if you want to nix that one from the list, adjust the numbers of all the others just slightly, you still come up with the same, jaw-dropping results.

Depending on how Stoudemire finishes up his New York stint, there's a chance he could be stricken from this list altogether. If he can stay healthy and productive, that contract might not be near as bad as it looked last year.

The rest just speaks for itself.

Gluttons for High-Priced Punishment

TOTAL DOLAN DOLLARS WASTED: $316 million.

What you can buy with $316 million: 787 Aston Martins, almost all of the 607 islands of Micronesia, being Batman.

Remember, these were just (some of) the worst of the worst contracts the Knicks have given out on James Dolan’s watch.

Extrapolate this out with what we’ve seen thus far this year (Andrea Bargnani) and other, smaller contracts over the years, we could be fast approaching the half-a-billion-dollar range.

If there’s one crucial caveat to this exercise, it’s this: To the extent that a lot of players who play in today’s NBA are probably making more money than they categorically deserve, New York is by no means alone in their money-dumpster fire ethos.

And yet, Dolan's Knicks provide a cautionary tale for how far a franchise can sink when managed by an owner with endless money at his disposal, and little to no idea of how to spend it effectively or efficiently.

Having league-wide salary cap is meant—in theory, anyway—to dissuade the game’s more swashbuckling owners from biting off more than they can chew.

Sadly, sometimes you just can’t stop a glutton. Especially when their meal of choice is basketball punishment.