Most Regrettable Non-Acquisitions in Baseball History

Yes, the Major League Baseball trade deadline is fast approaching. There have been many trades and acquisitions throughout the history of the game that have impacted teams on both sides. However, there have also been golden opportunities for teams to acquire a future star, but failed to do so. As the saying goes, "Sometimes the best deal is one that is never made." Well, how about the deal that teams fail to make? Here are my five most regrettable moves that teams failed to make in baseball history:

5. The New York Giants and Pittsburgh Pirates failing to sign Sandy Koufax

Sandy Koufax had a standout season at the University of Cincinnati in 1954, and was immediately spotted by a Brooklyn Dodgers scout. However, the Giants had brought him in for a tryout, and they did not offer him a contract. Koufax then left to tryout for the Pittsburgh Pirates. Sam Narron, the Pirates' bullpen coach who caught for Koufax, had his thumb broken by one of his pitches. Pirates general manager Branch Rickey said that he had the greatest arm he had ever seen. The Pirates hesitated to offer Koufax a contract, and did not do so until he had committed to signing with the Dodgers. Koufax went on to become one of the most dominant left-handers in the history of game, and a Hall of Fame career. Perhaps if the Pirates would have offered an earlier contract, the course of history could have changed drastically. Then again, the arch-rival Giants had a shot to offer him a contract, too.

4. The St. Louis Cardinals and Brooklyn Dodgers failing to sign Yogi Berra

Yogi Berra grew up on the "Hall of Fame" block in St. Louis where Jack Buck and boyhood best friend, Joe Garagiola, had also lived. However, Cardinal scouts thought that Garagiola was the better prospect of the two and chose to sign him after given the opportunity to sign either one. Branch Rickey, who was in his final year as team president for the Cardinals, had apparently planned on signing Berra when he took over operations for the Dodgers. However, the New York Yankees had given Berra a $500 signing bonus, and both sides agreed to a deal before Rickey could make an offer. Berra went on to help the Yankees to 14 World Series appearances while winning ten of them during his Hall of Fame career.

3. The Los Angeles Dodgers failing to sign Tom Seaver

The Dodgers had been one of the most successful teams in the 1960s, and Seaver had been drafted by them in 1965. However, the two sides could not agree on a contract in which Seaver asked for more than the Dodgers were willing to offer, so Los Angeles passed on signing him. The next year, the Atlanta Braves signed Seaver. But, the contract had been voided by MLB commissioner William Eckert because of his college team, Southern Cal, had played in two exhibition games that year with Seaver on the roster. Eventually, Eckert ruled that other teams could match the Braves offer, and the Mets were awarded Seaver after being amongst those who were willing to match. However, I can't fault the Braves for that, but the Dodgers had first crack at Seaver and did not sign him. He went on to help the Mets escape awful seasons by winning the 1969 World Series. His Hall of Fame career ended with three Cy Young Awards, too.

2. The Chicago Cubs failing to sign Joe DiMaggio

In 1934, Joe DiMaggio nearly ended his career prematurely when he tore ligaments in his left knee. His minor league team, the San Francisco Seals, were planning to sell him for $100,000, but after the knee injury, they had to try and give him away. The Chicago Cubs were given the opportunity for DiMaggio to have a risk-free tryout, but the team turned it down because of fears that his knee would never fully heal. The New York Yankees had finally been convinced to give the 19-year old player a tryout, and his knee passed testing. So he was bought from the Seals for $25,000 along with five other players, and he remained with San Francisco for the 1935 season. In 1936, DiMaggio's legendary career took off in a big way as the Yankees won four straight World Series. The Chicago Cubs had to be shaking their heads after seeing him go on to a Hall of Fame career.

1. The Philadelphia Athletics and Cincinnati Reds failing to acquire Babe Ruth

In 1914, Philadelphia Athletics manager Connie Mack had the first opportunity to acquire Babe Ruth from what was then the Baltimore Orioles minor league orginization. Orioles owner Jack Dunn had asked for $100,000 in acquiring Ruth along with two other players, but Mack declined the offer. The Cincinnati Reds were the next team that had the opportunity to acquire Ruth, and instead picked up two other players despite the fact the Reds had an agreement with the Orioles. So two days later on July 9, 1914, Dunn sold the three players that Mack declined to acquire to the Red Sox for what is still a disputed amount of money. Ruth made his debut two days later as a starting pitcher on July 11, and helped the Red Sox win three World Series during his tenure there. However as a good of a move as it was for the Red Sox to sign Ruth, that was all forgotten when the franchise sold him to the New York Yankees after the 1919 season. Ruth went on to help establish the Yankees as a powerhouse ballclub as well as becoming the most popular figure in baseball history. Many believe this is what started the heated Yankees and Red Sox rivalry.

These are the most important moves that could have been made, and that could have altered the course of baseball history. No one knows how any career will turn out, but the thought of them making a move or better offer to sign those players sure would have made someone else a better ballclub rather than where they ended up.

Sources: baberuth.com, baseballlibrary.com, joedimaggio.com, Amazing: The Miraculous History of New York's most Beloved Baseball team by author Peter Golenbock, yogiberra.com, wikipedia.com