The Orioles won their first World Series in 1966, but unlike the 1967 "Impossible Dream" Boston Red Sox, the Orioles rise to the AL Pennant shouldn't have been a big surprise to most baseball fans. They had been making steady improvement for a number of years.
After losing 100 games in 1954, the Orioles reached .500 by 1957, finishing 76-76. By 1960, the Orioles were very competitive going 89-65 in 1960 and 95-67 in 1961, but couldn't quite over take the Yankees. After a down 1962, the Orioles would win 86, 97 and 94 games from 1963-1965, before winning the pennant in 1966 with a 97-63 record.
Certainly, the trade to acquire Frank Robinson, before the 1966 season, was the piece that put the Orioles over the top. However, as a kid collecting cards at the time, I was unaware of another player that could have made the Orioles a dominate team through much of the 1960's. I had cards of Dean Chance, but never knew his connection to the Orioles.
Dean Chance was a pretty good pitcher for the Angels and Twins from 1962-68, winning 20 games twice and throwing an incredible 11 shutouts in 1964, on his way to the Cy Young Award.
Dean was actually originally signed by the Orioles around 1959 and pitched well in the minors for a couple years. He was drafted by the Washington Senators on Dec 14, 1960 as part of the expansion draft and traded to the Angels that same day. It's interesting to dream about how good the Orioles might have been had they been able to keep Dean Chance. The Orioles could have easily won a couple more pennants with him in the rotation.
There's not much out there with Dean pictured as an Oriole, but here's a couple items.
1959 Orioles team issued 8x10 photo
Chance, Dean 1.jpg
1960 Baltimore News-Post Scrapbook card
1960 Baltimore News-Post Scrapbook #12 (Chance, Dean).jpg