1933 was Ruth’s second to last year with the Yankees. Though that may sound like a bit of a random season to fetch such a high price, the significance of 1933 is that it also marked Ruth’s first all star selection and, unsurprisingly, the year he hit the first home run in all star game history. For those wondering why Ruth didn’t make an all star team until 1933, the answer is simple — that was the first year the game even existed.

This dinger, hit on August 7, 2008, broke Hank Aaron’s long-standing all-time career home run record. The ball was caught by Matt Murphy, a 21-year old student who entrusted it to Sotheby’s auction house for sale. The winning bidder was fashion designer Mark Ekko, who laser etched an asterisk into it before sending it to the Hall of Fame.

Unbelievably, a different Bonds home run ball has arguably had a larger impact on society. His single season record setting 73^rd home run ball in 2001 caused a fight in the stands over ownership. The lawsuit that ensued, Popov v. Hayashi, cast light on some arcane property law principles, primarily the concept of abandoned property. To stress just how rarely this particular issue has arisen, the primary sources of precedent on which the decision hinged were 19^th century fox hunting and whaling cases. Popov won and sold the ball for $450,000, but the real winners were property law professors who finally had a case less than 200 years old to demonstrate these concepts to first-year law students.

This piece, sold by Mastro Auctions in August 2005, seems a bit underwhelming given the history connected with the other items on the list, but it splendidly illustrates an important tenet of auction sales: condition matters. Ruth only wore this obscure uniform a few times, mostly during an offseason tour of Japan, but because of its infrequent use, it’s still in fairly pristine condition for a garment that old. More importantly, it’s a complete uniform, with socks hat and all which adds to the price.

The first homer hit at the first all-star game — in Comiskey park in 1933 — this item is so valuable because it’s a double header (hooray, baseball puns). It has historical value, marking the first home run in all-star game history, but it also holds celebrity value, given that it was signed by Ruth, whose signature on any item would fetch a hefty price, let alone a one-of-a-kind piece with such history of it’s own. This ball was kept in chests and closets — even spent a decade in an old cardboard box — by the family of the man who caught it for the better part of a century before it was sold at a memorabilia auction at Major League Baseball Fanfest in Pittsburgh in 2006.

This is the Jersey Ruth was wearing during, arguably, his most famous moment: his called shot against the Cubs in game 3 of the 1932 World Series. There’s some debate as to whether Ruth was actually pointing where he’d hit the ball, if he was simply pointing at the pitcher or just gesturing in general. However, the idea of a called shot, let alone in the World Series, is too iconic of an image to really question which is why this item fetched such a hefty price at a Grey Flannel Auctions sale in 2005.

This document, which marks the sale of Ruth from the Red Sox to the Yankees, is perhaps the most famous (or infamous, if you’re not from New York) transaction in baseball history, launching a Yankees dynasty that’s won 27 World Series since, and cursing the Red Sox to 86 years of futility before they exorcised that particular demon in 2004. The sale price, realized at a 2005 Sotheby’s auction, made this the most valuable sports document ever sold by a fairly wide margin, though it has since been surpassed by a 2010 sales of James Naismith’s original rules of basketball for a staggering $4.3 million (also at Sotheby’s).

This item, sold by Sotheby’s in 2004, is the only bat on the list for several reasons. First, Ruth used it during the first game ever played at the original Yankees stadium in 1923. Second, he hit a home run with it — the first home run in the history of the infant stadium. Third, the opponents were the Boston Red Sox, who sold Ruth to the Yankees several years prior.

The most famous and valuable baseball card of all, this card was part of a 1936 set that was issued by tobacco companies to stiffen cigarette packaging. It’s value stems from the fact that not only was Wagner arguably the best player of that era, but he took a personal stance against smoking, refusing to allow his image to be used by The American Tobacco company because he didn’t want to encourage children to buy cigarettes. As such, these cards are exceedingly rare, with only 57 believed to be still in existence, most of which are in rough shape. This particular card, featured in a ESPN 30 for 30 short, was deemed to be in near mint condition at the time of this sale by Mastro’s in 2007 which accounted for much of its value.

However, there is controversy surrounding it, as in 2013, Bill Mastro, owner of the auction house of the same name, admitted to altering the card prior to sale, shaving the edges and helping it achieve the near mint evaluation. The company went out of business while under investigation in 2009, and Mastro was sentenced to 20 months in prison for shill bidding (that’s not one you see every day).

Deemed “The Crown Jewel of Sports Memorabilia” when it was put up for sale at Guernsey’s in 1999, this ball marked McGwire’s coronation as the new single-season home run king, shattering the previous record of 61, and for a decade was the most valuable piece of sports memorabilia ever sold. It also hearkens back to a simpler time when we could watch sluggers like McGwire and Sammy Sosa rewrite the record books without ever wondering if they were on something “extra.”

The ball was purchased by comic author/artist Todd McFarlane, most famous for his creation, Spawn.

Just when you thought you were done with The Babe! This is the oldest-known surviving game-worn Ruth jersey and was characterized to the New York Times in 2012 as “The Holy Grail of Sports Memorabilia” by David Kohler, President of SCP auctions (which may be just a bit biased since they were the ones selling the thing). Nonetheless, you can’t argue with results and this one speaks to the enduring celebrity and force of personality of the Babe. Interestingly, the winning bidder was Leland’s, another auction house. Presumably, they think they can sell it for more.