James Shields poised to become an all-time Hot Stove bust

Let's start today by catching up on recent Pop Quiz questions:

1) From Sam Lerman of Queens: In a legendary 1992 episode of "The Simpsons," Mr. Burns hires a team of major-league ringers for the power-plant softball team. Name the six (of nine) ringers who played for the Yankees during their careers.

2) From Gary Mintz of South Huntington: In a 2001 episode of "Curb Your Enthusiasm," Larry David helps a charity for a (fictional) illness that he assumes is named after a shortstop who played primarily for the Pirates. Name the fake disease and the real player.

3) From Mintz, again: Name the current owner of a major-league team who appeared on a 2010 episode of "Undercover Boss."

— Jon Morosi of Fox Sports reports that James Shields, the last remaining free agent who requires draft-pick compensation (because he rejected Kansas City's qualifying offer), is expected to sign a contract before the end of the week.

If that occurs — and getting information on Shields' free agency has proven more challenging than solving the puzzle of Jerry's Roommate Switch in this "Seinfeld" episode — then we'll have the answer to the question that has been circulating (at least, around my brain) recently:

Is Shields in danger of becoming the biggest free-agent bust in Hot Stove history?

By "bust" in this context, I don't mean the player's performance after signing a contract. I mean the contract itself. We're talking expected payday vs. actual payday.

There's no official measure of this, since there's no official "Expected" figure. We can go only anecdotally.

The most legendary tale is that of Jody Reed, who now works in the Yankees' minor-league system. During the 1993-94 offseason, as you can see in this story, Reed turned down a three-year, $7.8-million offer to stay with the Dodgers — before he entered the market — and wound up signing with Milwaukee for just $350,000 guaranteed.

Beyond that, you think of three cases from just last year. Nelson Cruz, Stephen Drew and Kendrys Morales turned down their team's qualifying offers of one year and $14.1 million, and all three lived to regret that decision, although some longer than others. Cruz signed with Baltimore for one year and $8 million and mashed his way to a four-year, $57-million deal with Seattle.

Stephen Drew's free agency gamble failed miserably.Photo: Paul J. Bereswill

Drew and Morales extended their free agencies into the regular season and signed pro-rated deals — Drew with Boston, Morales with Minnesota — and both men wound up getting traded, Drew to the Yankees and Morales back to Seattle, whose qualifying offer he had rejected. Morales recovered slightly from the debacle by signing a two-year, $17-million contract with Kansas City, while Drew slinked back to the Yankees for one year and $5 million.

There lies an obvious difference between that trio and Shields, however. Cruz was coming off his suspension for Biogenesis, whereas no one viewed Drew and Morales as top-of-the-market guys.

Shields entered this market as the number three starting pitcher, easily, behind Max Scherzer and Jon Lester. He has age (33) and mileage on the negative side of his ledger, although a good agent would spin that mileage positively into "dependability." He also carries an excellent reputation when it comes to clubhouse presence and leadership; the Royals credit him with helping their young pitchers develop into the pennant-winning group they became in Shields' two years there.

Given the health of the industry and Shields' skill set, a four-year, $80-million contract seemed like a conservative guess. I predicted that Shields would get five years and $100 million from Boston.

So how much will he wind up getting? One official from an American League team said Tuesday that Shields' asking price had dropped to $60 million over three years.

The Yankees, with their payroll close to last year's number, don't seem very interested. Morosi mentions San Diego as a possible suitor, and signing Shields would make the Padres' winter even more electric than it already has been. Milwaukee seems like an obvious candidate, as Brewers owner Mark Attanasio has a history of late-offseason free-agent signings like Matt Garza last year and Kyle Lohse two years ago.

The third-highest contract signed by a starting pitcher this offseason is the four-year, $55-million contract that Ervin Santana signed with Minnesota. Santana is 32, just one year younger than Shields, and nowhere as consistent or accomplished.

So let's set that number, $55 million, as the bar for Shields' free-agency legacy. If he and his little-known agent Paige Odle can't exceed that, then Shields should join Reed in the annals of all-time Hot Stove underachievers.

–Your Pop Quiz answers:

1) Wade Boggs, Jose Canseco, Roger Clemens, Don Mattingly, Steve Sax and Darryl Strawberry

2) Groat's Disease, Dick Groat

3) Todd Ricketts of the Cubs

If you have a tidbit that connects baseball with popular culture, please send it to me at kdavidoff@nypost.com.

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