"Sometimes the best trades are the ones you don’t make” is a popular sports adage that originated in baseball, but has been used by other sports as well. “Of Keltner, Veeck remarks that ‘sometimes the best trades are the ones you don’t make’” was cited in print in October 1948. Cleveland Indians owner Bill Veeck (1914-1986) creating the saying, and his Cleveland Indians won the 1948 World Series based on Veeck’s non-trades.
It’s often stated that the non-trade involved Indians player-manager Lou Boudreau (1917-2001). However, the 1948 newspaper article states that the non-trade involved Indians third baseman Ken Keltner (1916-1991).
“Sometimes the best trades are the ones you don’t make” has also been used outside of sports, such as in finance.
Wikipedia: Bill Veeck
William Louis “Bill” Veeck, Jr. (/ˈvɛk/; February 9, 1914 – January 2, 1986), also known as “Sport Shirt Bill”, was a native of Chicago, Illinois, and a franchise owner and promoter in Major League Baseball. Veeck was at various times the owner of the Cleveland Indians, St. Louis Browns and Chicago White Sox. As owner and team president of the Indians in 1947, Veeck signed Larry Doby and thus successfully integrated the American League. Veeck was the last owner to purchase a baseball franchise without an independent fortune, and is responsible for many innovations and contributions to baseball.
6 October 1948, The Daily Ardmoreite (Ardmore, OK), “One Trade On, One Trade Off—Indians Benefited by Both” (AP), pg. 10, cols. 6-7:
Of Keltner, Veeck remarks that “sometimes the best trades are the ones you don’t make.”
In the months preceding the 1947 season, Veeck had the 32-year-old third baseball on the block. He was attempting to pick up a first class starting pitcher or a center fielder in a swap.
Veeck finally gave up on a trade, called Keltner to Cleveland, gave him a raise and told him he would stay with the Indians.
Keltner responded by having two great years.
6 July 1950, Richmond (VA) Times-Dispatch, “The Sportsview” by Chauncey Durden, pg. 20, col. 1:
BASEBALL TRADING is a risky business. So much so Bill Veeck once observed that the best trades sometimes are the ones that are never made.
19 February 1956, Cleveland (OH) Plain Dealer, “Pinch Hitting” by Harry Jones, pg. 2-C, col. 1:
Hank continued to tinker and in 1954 a pennant was won. It was won more because of what he wisely didn’t do. Who was it that said the best trades are the ones you don’t make?
7 June 1959, Boston (MA) Sunday Herald, “Unheralded Hurlers Spice A. L.” by Ed Costello, pg. 64, col. 2:
There’s a saying among some baseball folks, “The best trades are the ones you don’t make.”
17 April 1962, Boston (MA) Herald, “Cold May Delay Sox and Indians,” pg. 30, col. 6:
All of which brings to mind the words of Red Sox manager Mike Higgins when trades fall through, “Sometimes the best trades are the ones you don’t make.”
26 June 1967, Boston (MA) Traveler “Tillman Finally Feels Wanted” by Tim Horgan, pg. 15, col. 1:
One of baseball’s many axioms is that the best trade is often the one you don’t make.
13 August 1974, The Evening Times (Trenton, NJ), “Best Trade Phils Made They Didn’t” by Bus Saidt, pg. 16, col. 4:
As some baseball expert in the sky once said, it’s the trade you don’t make that might be your best trade.
3 October 1974, Mobile (AL) Register, “High-paid Reds again a puzzle” (AP), pg. 5-D, col. 2:
“Sometimes people say the best trade is the one you don’t make,” he (Bob Howsam, club president of the Cincinnati Reds—ed.) said.
The Pro Football Mystique
By Dave Klein
New York, NY: New American Library
“Sometimes, the best trades are the ones you don’t make.”
“A good trade is one that makes both teams happy.”
A Baseball Memoir
By Terry Pluto
New York, NY: Simon & Schuster
Veeck told everyone that the Indians won the 1948 pennant late in 1947, when he decided to listen to the fans and not trade Boudreau. He even was credited with being the first baseball executive to say “Sometimes, the best trades are the ones you never make.”
Baseball’s Greatest Maverick
By Paul Dickson
New York, NY: Walker Publishing Company, Inc.
The non-trade (of Lou Boudreau—ed.) inspired a legendary Veeckism: “The best trades are the ones you don’t make.”