If you have been paying attention to the free agent market this winter, then your head is likely spinning from the amount of zeroes that have been thrown around thus far. Cliff Lee led the way, having spurned more guaranteed money from two other suitors to ink a pact that could potentially be worth $135 million over six years. Carl Crawford just signed a seven year mega-deal with the Boston Red Sox for a whopping $142 million. This was on the heels of another hefty pact agreed to by the Washington Nationals and Jayson Werth for a total of $126 million, also for seven years. After the dizzying dollar figures that have been handed out, I figured there was no better time to examine the recent history of some similarly lucrative agreements with the added value of hindsight. To date, there have been 26 contracts signed with an average annual value (AAV) equal to or greater than $18 million. To no one?s surprise, none of these contracts were signed before the new millennium. What is surprising is that general managers continue to use the contracts signed around that time as a baseline for what to give the superstars of today. It is no secret that the steroid era, and the offensive production that presumably resulted from it, influenced what marquee players received on the open market. In fact, five out of the first six contracts with an AAV equal to or greater than $18 million were signed by players who have since admitted to or been exposed as users of performance enhancing drugs, with the exception being Derek Jeter. That?s not to say that the players didn?t necessarily live up to their contracts. I analyzed these 26 contracts and asked a simple question: right now, if you could go back in time, knowing what we know now, would a team sign this contract again based solely on the performance of the player? More simply put, does the signing team regret the contract? Even though I mentioned it above, I am trying to leave performance enhancing drugs out as a determining factor in whether or not a contract is regrettable. Of these contracts, I deemed that four of them are too early to make a determination of regrettable or not. Included in that group are the two from this offseason that are mentioned above as well as Joe Mauer and Mark Teixeira. It is merely too early in the span of the contract to make a decision either way. Mind you, this practice is purely subjective, but I believe that most of you would agree with a vast majority of the determinations. Amazingly, the remaining 22 contracts with an AAV of at least $18 million were split right down the middle when deemed regrettable or not. As a rule, short term deals are very hard to characterize as regrettable, seeing as they are not hampering a team in the future and can be shed at season?s end. The three shortest contracts in this analysis all belong to the same player: Roger Clemens. These were the Rocket?s last three seasons when he was hemming and hawing about whether or not to play a la Brett Favre. The last two seasons, 2006 and 2007 were pro-rated portions of the AAV?s used to include them in this analysis, so, in reality, they didn?t cost the signing team nearly as much. The other two short term contracts, oddly enough, were two year pacts signed by players with the same team, the Los Angeles Dodgers. I assume that the Dodgers, if given the chance, would definitely take back both of these commitments if they had the chance. Andruw Jones? deal is an easy one to deem regrettable, but Ramirez?s was a little tougher to determine. However, the deciding factor is the reality that Mannywood only played in roughly half of the team?s games over the course of the contract. So, even though his numbers are impressive, I can?t sit here and say that great statistics warrant the $22.5 AAV when he appeared in so few games. On the other end of the spectrum, contract length-wise, there have been 12 pacts signed that were seven years or longer. Four of those are the ones that are too soon to tell. Two of them are the poster boys for bad contracts in Barry Zito and Vernon Wells, both having signed seven year, $126 million deals. These were the easiest determinations of the bunch. Ironically, this is the exact same contract length and value of the Jayson Werth deal. That can?t be a good omen for Nationals fans. Another two of the long-term variety were both 10 year contracts signed by the same player, Alex Rodriguez. Even though A-Rod has produced numbers that are historic, I don?t think it is a stretch to assume that the Texas Rangers would think again if given the chance. This is especially true, given the restrictive nature of the contract as it relates to total payroll. When you factor in the bonus payout, the Rangers were allotting slightly less than half of their total payroll to Rodriguez in 2001. In 2002 and 2003, Texas more than doubled their payroll in an attempt to reach the playoffs only to win fewer games in both seasons than they had in 2001. The New York Yankees are dealing with the most recent ten-year contract and even with their seemingly unlimited resources, it is apparent that they would love to be able to take a mulligan. The two most prominent reasons for this are Rodriguez?s offensive production tailing off in addition to his injury problems. There may be some disagreement out there whether you can deem both of his contracts regrettable, but in my book, I think both front offices would rescind these decisions without thinking twice. That leaves four contracts of at least seven years in duration and no less than $18 million in AAV. The longest of the four is Derek Jeter?s 10 year, $189 million deal signed in 2001 that just expired after this past season. Jeter performed incredibly well over the life of the contract despite a couple down years, not to mention he is the undeniable face of the franchise and embodies the ?Yankee Way.? The Yankees are unlike any other franchise, as Jeter is worth more to them than he would be to any other team. I cannot find any way to characterize this contract as regrettable. I have no doubt that Brian Cashman would do this deal again in a split second. The next contract is the eight year, $160 million deal that Manny Ramirez signed with the Boston Red Sox before the 2001 season. Throughout the length of the contract, Ramirez was one of the most prolific right-handed hitters of all time. Was he flaky? Indeed. Did he have run-ins with teammates and management? Absolutely. However, did he live up to the lofty standards established by signing a contract as massive as he did? I can?t think of another way to answer that question than with a definitive ?yes.? The next two are both very early on in the contract term, so the decision to deem them as not regrettable is one that could change in a few years. However, both players have performed so well early on in the deal that I believe it is safe to assume that they will continue to do so. Lest we forget, this practice is centered around whether or not a general manager would void this deal if he could go back in time and do so. Seeing as C.C. Sabathia has pitched like every bit of the ace he was purported to be over the first two years of his contract, I can?t see Cashman regretting the decision. Ditto for Miguel Cabrera, who has been nothing short of the best power hitter in the American League over the first three seasons of his eight year pact. The remaining nine contracts that range from three to six years in length are a mixed bag and aren?t as easily categorized as the ones analyzed above. However, what they do have in common is that five of them I consider regrettable, while the other four are not. The theme of this exercise has become clear. There is a 50/50 success rate when handing out these massive contracts. There aren?t a plethora of teams in Major League Baseball that can assume this kind of risk. The Texas Rangers are a cautionary tale when considering this. They got more production than they could have imagined from signing the biggest contract in history at the time and even that wasn?t enough to financially justify keeping Alex Rodriguez around. If history serves as precedent, out of the quartet of Carl Crawford, Jayson Werth, Joe Mauer and Cliff Lee (all of whose new deals will begin in 2011), two of these contracts will have their respective general manager pleading for a do-over. Which two will it be? Jason Follain is the Senior Baseball Writer for RealGM.com. Please feel free to send comments, suggestions and feedback to Jason Follain directly at [email protected]

Player	AAV (millions)	Start Year	End Year	Regrettable?	Length	Total Value (millions)	Team
Roger Clemens	$28.00	2007	2007	No	1	$28.0	Yankees
Alex Rodriguez	$27.50	2008	2017	Yes	10	$275.0	Yankees
Alex Rodriguez	$25.20	2001	2010	Yes	10	$252.0	Rangers
Ryan Howard	$25.00	2012	2016	Yes	5	$125.0	Phillies
Cliff Lee	$24.00	2011	2015	?	5	$120.0	Phillies
C.C. Sabathia	$23.00	2009	2015	No	7	$161.0	Yankees
Joe Mauer	$23.00	2011	2018	?	8	$184.0	Twins
Johan Santana	$22.92	2008	2013	Yes	6	$137.5	Mets
Manny Ramirez	$22.50	2009	2010	Yes	2	$45.0	Red Sox
Mark Teixeira	$22.50	2009	2016	?	8	$180.0	Yankees
Roger Clemens	$22.00	2006	2006	No	1	$22.0	Astros
Carl Crawford	$20.29	2011	2017	?	7	$142.0	Red Sox
Roy Halladay	$20.00	2011	2013	No	3	$60.0	Phillies
Manny Ramirez	$20.00	2001	2008	No	8	$160.0	Red Sox
Miguel Cabrera	$19.04	2008	2015	No	8	$152.3	Tigers
Derek Jeter	$18.90	2001	2010	No	10	$189.0	Yankees
Carlos Zambrano	$18.30	2008	2012	Yes	5	$91.5	Cubs
Andruw Jones	$18.10	2008	2009	Yes	2	$36.2	Dodgers
Roger Clemens	$18.00	2005	2005	No	1	$18.0	Astros
Ryan Howard	$18.00	2009	2011	No	3	$54.0	Phillies
Sammy Sosa	$18.00	2002	2005	Yes	4	$72.0	Cubs
Barry Bonds	$18.00	2002	2006	No	5	$90.0	Giants
Torii Hunter	$18.00	2008	2012	Yes	5	$90.0	Angels
Ichiro Suzuki	$18.00	2008	2012	No	5	$90.0	Mariners
Barry Zito	$18.00	2007	2013	Yes	7	$126.0	Giants
Vernon Wells	$18.00	2008	2014	Yes	7	$126.0	Blue Jays
Jaysen Werth	$18.00	2011	2017	?	7	$126.0	Nationals