'Transmission' at The Cub Reporter has an excellently researched article on the failed 1992 Greg Maddux negotiations:

According to Maddux, a no-trade clause and the Cubs tardiness at returning a phone call meant the difference between signing or rejecting a five year, $25 million extension. Maddux went into 1992 without that extension, made $4.2 million for the season, while Scott Boras continued negotiations with the Cubs. (WSJ 11/6/1992)

That season Maddux pitched like a man in search of a record-setting contract. In 35 starts he went 20 and 11. Thats 4 no-decisions in the entire year. 34 out of his 35 starts went 6 innings or longer. As Boras continued to negotiate a contract during the month of July, Maddux lowered his ERA from 2.54 to 2.21. The super-agent was looking for five years at $28 million. Cubs GM Larry Himes responded with an offer of a five-year, $27.5 million contract - a raise of $2.5 million overall, or 500,000 per year, from the offer that Maddux nearly had accepted that winter.

Maddux rejected it.

That off-season, Maddux filed for free agency on the first day possible. Himes quickly announced that while his top priority was to re-sign Maddux, he would not get into a bidding war and he would not delay pursuit of other free agents with money that might have been ear-marked for the reigning Cy Young.

Read the rest.