Right but he also "lost money" by playing the last 2-3 years at below market value, which he did. More bites at the apple means you want more chances to bite the apple. In this case, he's gotten less chances, because he's literally in year 6 and hasn't bitten the apple once yet.
The other reason this "report" doesn't make a lot of sense is that IF Lamar's desire is short term deals, and IF you believe what Lamar is saying is gospel, he turned down 3/133, fully gtd, already. So he was offered a short term at a very fair price, and turned it down.
I don't think there's a person on the planet at this point that thinks if he was offered 3/150, fully gtd, today, that he takes it. And if he's not taking that, then its clearly not about "shorter terms" or "more bites".
One other thing to note about the contract lengths is there's nothing that says Lamar had to sign a 4,5,6 year extension two years ago. Could have been a 2-3 year extension, which would make him a UFA in 2025-2026 timeframe. In which cases, he'd be significantly richer than he is now, he'd be a UFA in as little as 2-3 years, and frankly, by 2024/2025, he'd be back negotiating another extension at new market prices anyway. So he'd be in the same spot he's in next year (i.e. negotiating a market-rate contract), with more $ in his pocket already.