Yankees: The worst trades in franchise history

There is a long and storied history behind the New York Yankees franchise. Countless players have come and gone over that time through trades. These are the 15 worst Yankees trades in franchise history, each an instance where hindsight suggests the Yankees were fools. 

Pick any year in Yankees history and you’ll find a host of famous and familiar names up and down the roster. Some were homegrown, players the club scouted, signed, and developed on their own. Some were brought in as free agents, signed to lucrative contracts largely powered by being one of the richest clubs in all sports. Some came to wear pinstripes via trades.

Not every trade worked out in New York’s favor, however.

Sometimes the club acquired the wrong player. Sometimes the mistake came in who they gave up. Context is always a factor, but ultimately it is really the power of hindsight that makes a deal look like a poor one.

15. July 13, 1987. New York trades Bob Tewksbury, Rich Scheid, and Dean Wilkins to the Chicago Cubs for Steve Trout.

Steve Trout (no relation to Mike) was having a fine start to the 1987 season. He was 6-3 through 11 starts, with a trio of complete games. His 3.00 ERA through 75 innings was well ahead of the National League average. Trout’s 1.320 WHIP was the best mark of his career.

Things fell apart quickly after Trout joined the Yankees, however. He’d make nine starts for the club before shifting to the bullpen. He’d only throw 46.1 innings over the remainder of the season, posting an 0-4 record and 6.60 ERA.

New York let Trout leave as a free agent following the season. He’d land in Seattle where he’d struggle through two more seasons before calling it a career.

Neither Scheid nor Wilkins (both former second-round draft picks by New York) produced much in their careers. Scheid would have brief stints in the majors with Houston in 1992 and the Marlins in 1994 and 1995. His career totaled just 54.1 innings. Wilkins threw a total of 31 innings for the Cubs between 1989 and 1991. Bob Tewksbury was the big piece the Yankees would regret moving.

The right-hander had gone 9-5 with a 3.31 ERA in 1986, his rookie season. He struggled to begin 1987 though, posting a 1-4 mark and 6.75 ERA through six starts and a pair of relief appearances. Once he arrived in Chicago, the rough season continued and he found himself back in the minor leagues.

Tewksbury’s career would rebound. He’d pitch through the 1998 season, finishing with 110 wins and a career 3.92 ERA.