money isn't everything.
"You have to live life to its full chorizo!"-Mario Batali

I always figured that Ty basically deposited a bunch of checks at once, spent his money until he was broke and didn't get around to depositing more money until he started bouncing checks.
Businesses that were familiar with Ty probably knew he was "good for it" and gave him some extra time to make good on the money, but if he bought something expensive without having the money in the bank from a company that didn't know him, they probably would have sued him for fraud once the check bounced, hence the court summons.

I wish I had the life of a Ty Webb.
"'Extremely High Voltage.' Well, I don't need safety gloves, because I'm Homer Simpsozzzzzz" - Frank Grimes

Actually, the uncashed check was for 70 thousand dollars, and then she said "Theres a bunch of them, and a summons". They guy had it made, and it was pretty pathetic that he could not even bother to drive to the bank and deposit them.

That's how much I make in a year (before taxes)

I got a good idea. Lets pretend we're real human beings.

then how does he compare himself to other golfers? lol

$50,000 in one lump sum is still quite a bit of money.
dies ist meine unterschrift

Long time since $50,000 was a lot of money. A rookie Policeman would earn more than that in a year now.

I think you're giving this one way too much thought. Lol. She calls him pathetic, because he is so lazy and spoiled, that he can't even put forth the effort to cash a bunch of checks for substantial sums of money($50,000 would be worth more than twice that much now). And he was an excellent golfer. He carried a horrendous Al Czervik, despite the efforts of a cheating judge Smails. Also, don't forget, he owns a lumber yard, but doesn't even know where it is. That sums up how lazy/spoiled he is. Hence the term pathetic.
"The key is, you've got to be crazy to maintain your sanity"

I had always presumed that he was kind of on the margins of being wealthy and being a complete fraud.
His family is what got him the golf membership (why the Judge knows him) but he doesn't have any fresh bottles of perrier. Most of his story is made up and even his golf game isn't that great.
I was always under the impression that the checks were fake and on display to impress girls who didn't know any better. Lacey comes from a wealthy background and didn't fall for it.
I could be wrong, but that's how I've always thought it was.

So why did Lacey say it was "pretty pathetic" when she found the checks?
"I will not go down in history as the greatest mass-murderer since Adolf Hitler!" - Merkin Muffley

My guess is Ty Webb's Dad was extremely rich. The checks that Lacy Underall found were just money from the stock market that just kept rolling in for Ty. He'd cash them eventually, but there was no hurry because he was swimming in money.

Keep it.

He wasn't even in the war in Vietnam.
"I will not go down in history as the greatest mass-murderer since Adolf Hitler!" - Merkin Muffley

He lived his life outside of the realms of our understandings of a logical person. He doesn't even keep score.