NEW YORK, NY – Among the many great scenes from Oliver Stone’s “Wall Street” was one that included an exchange between Bud Fox (a pre-porn Charlie Sheen) and Marvin (a pre-Scrubs John McGinley) McGinley goes on and on about the kind of money Dave Winfield is making at the time. Winfield’s free agent contract with the Yankees in the Winter of 1980 was for 10 years and $23 Million. $2.3 Million Dollars. Per Year! Wow! Mind boggling numbers at the time, and other than Howie Spira and being known as Mr. May, a pretty good signing for a guy who was damn good (in the regular season) somehow even a bit underrated and who would go on to the Hall of Fame.
George Steinbrenner was a lot of things. According to Billy Martin, he was a convicted liar. (Reggie was a born liar) Say what you wanted about The Boss but when he saw a guy out there whom he believed could help his team win, George went and got him. Steinbrenner made his share of mistakes in trades and Free Agency signings, but he took chances and was not afraid to fail. Unlike Real Sandy Alderson, who has virtually no money to spend; no integrity to point to, and no knowledge seemingly of the current financial landscape of Major League Baseball.
Sandy, you want to go to the grocery store because your family is hungry. You want some steak, but it’s 12 dollars a pound. So you look at the chicken instead and see that it’s less expensive than the steak, but at 6 dollars a pound, it’s more than you want to spend. Your kids are hungry, but the food you’d like to buy is too much money in your eyes, so you head home empty handed allowing your family to starve to death. Rather than enabling your family to thrive, you’d rather be right Real Sandy, and wait until prices fall to what YOU believe is fair. You tell your kids that you have money to buy groceries, but you just don’t like what the store is charging for those groceries. Eventually you believe, you’ll get your filet mignon for 89 cents per pound and your lobster for a nickel. 
Sometimes, free agency signings don’t work out. But you have to take shots sometimes. You can draft well, make shrewd trades. But occasionally you have to throw caution to the wind and spend some dough. Real Sandy remains deathly afraid of landing on this list, so he sits idly by-much like my No. 5 on my list of worst Free agent signings in MLB over the past dozen years.
5. Carl Pavano. What can you say about the American Idle. 26 starts across 4 years for $39M. This guy made Matt Kemp look like Lou Gehrig.
4. Alex Rodriguez. Which contract? Do you realize that A-Rod since 2002 has signed contracts totaling over half of a BILLION dollars? Cheating all the way, his fat face screams…”smash me with an ashtray!”
3. Albert Pujols. When all is said and done, this may well go down as the worst contract in sports history. No one other than erstwhile Mets scrub reliever Jerry DiPoto actually believes he’s 33. Albert is already pushing 40 and still has over $200M coming his way from the owner-Arte Moreno-who is easily the least talked about moron owner in Sports.
2. Julio Lugo. You know how after the Red Sox won the Series this year everyone kept referring to the Red Sox approach as the Red Sox “model” of building a team? Well, before they crafted this new age model, the Red Sox were just a crappy rich team who shelled out as many bad contracts as any other team. Before their “model” year in 2013, there were signings and acquisitions of guys like Adrian Gonzales, Carl Crawford, Josh Beckett...and Julio Lugo. In 2006, Lugo boasted an On Base Percentage of .373 Based exclusively on this and their Sandy-like belief that they were smarter than everyone else, Theo Epstein gave Julio “Friggin” Lugo 4 years and $36Million Dollars. After signing that big deal, Lugo never had another year in which his OBP exceeded .284
1. Jason Bay. Among the top 5 most proven run producers in the game through 2009, Bay was a lock to give the Mets solid production in the middle of their lineup for 4 years. Instead Bay gave Mets fans diabetes. The popular narrative now tells us that Bay tailed off after a series of concussion during his first year with the Mets. The reality is that he had 3 HRs through August in his first season in Flushing, and then smashed his head against the wall in Dodger Stadium. The dye had already been cast at that point. 4 years. $66M. The Met curse indeed.
And Finally, Is this George Steinbrenner’s oldest son Hank? Or is this Babe Ruth’s grandson?
Our very own Babe Ruth – Angry Ward – tomorrow.
