Thanks for the chart, Moon. Maybe the big extensions in 18/19 that kept Sale and Bogaerts from becoming free agents should be included, since the earlier Ortiz extensions were listed. I guess then other biggies like Pedroia's, AGon, and Pedro's first, too.
One thing for sure: the top numbers on the red contracts for the most part were massive overpays or abject failures. Price at 217 is the real sore thumb (despite three good starts in Oct '18), then in order come Crawford 142, JD 100, Pablo 95, Hanley 88, Eovaldi 68... though JD -- two great seasons, one bad -- and Incomplete Nate could still be good earners.
Nevertheless, I agree with posters who state that signing top talent will always require longer contracts. We're not going to have a shot at a guy like Juan Soto in five years if we offer half as many years as New York or LA (but maybe the glut of star free agent shortstops next winter will change parameters).
I also fully expect Mookie will be worth his market value as a fan favorite and productive Dodger for the next six seasons, whether LA ever wins another ring.