The saying “A fool and his money are soon parted” was attributed to the poet Thomas Tusser way back in 1557. There is also a biblical reference to the turn of phrase in The Book of Proverbs. Either way, the saying has been around for a long time. Baseball fans like to have the shiny new toy beneath the Christmas tree each off-season in the form of a new big-name free agent. I think we can all agree it is fun to spend the team owner’s money This is the time of year when trade conversations start to pick up steam as the haves and have not’s are more clearly defined. Those shiny free agents become players to be moved off of the rosters of teams who have underperformed or are simply not talented enough to compete for the post-season. The most likely guys to move are those expensive players who were once the apple of the eye of a particular fanbase. Clubs will make interesting decisions about the directions of their clubs as the deadline approaches. I am always curious to see how the big off-season deals work out with the benefit of time and hindsight. I don’t begrudge the team for offering the deals as no one wants to waste millions of dollars on purpose, and by the same token, I don’t hold accepting the deal against the players because anyone would take the kinds of money the clubs are offering. I wanted to see how many of these expensive contracts worked out, and focus on the positive here. It is easy to slam the Baltimore Orioles’ deal with Chris Davis where they paid him $161 million dollars over seven seasons; a deal which netted the club a -2.7 WAR over the lifetime of the deal. However, when we look back to when the deal was signed Davis was coming off of a season in which he led the league with 47 home runs. Simply put, it made sense at the time. I looked at the top 50 deals by total contract value and saw there were some good deals mixed in with clunkers. The first obviously mutually beneficial deal I came across was the Max Scherzer deal with the Washington Nationals, which ran from 2015-2021. It was seven years and $191.4 million dollars. Over the life of the deal, Scherzer amassed 42.5 bWAR. He was dominant for the life of the deal. Let us not forget he was instrumental in 2019 as the Nationals won the World Series. Scherzer was in the top 5 for Cy Young voting in six of the seven years of the deal. This is what everyone hopes for when signing a player to a large deal. The Justin Verlander deal with the Detroit Tigers was another successful deal. The decade-long deal with the Tigers was from 2010-2019. The deal saw the ups and downs for Verlanderm(He led the league in earned runs allowed in 2014), but he still left Detroit at the trade deadline with gas left in the tank as evidenced by his Cy Young Award in 2019, the final year of the deal. He provided 56.6 bWAR to his clubs, making him one of the best pitchers of his era. I haven’t forgotten about the Alex Rodriguez deals. The 2001-2010 version of the deal is the best one. Signed with the Texas Rangers, he won three Most Valuable Player awards during the deal. The hit over 50 home runs three times. He was on a World Series winner in 2009. This was peak A-Rod. The 7.2 bWAR per season is the highest annual average among the top 50 baseball contracts of all time. We can argue about how the numbers A-Rod put up were derived, but the stats are what they are, which makes him one of the most dominant offensive forces the game has seen. In reviewing the deals, it looks like the makes more sense to sign guys who are truly elite. The best ones are deals for guys on a hall of fame track. Signing guys who are good at the moment, but who are not destined to become greats see a much more variable return on investment for the owners and much more angst for the fans. Long-term deals for players in the class of Matt Kemp worked out much worse than the ones for legends like Derek Jeter.