The original Sad Sam Jones was named Samuel Pond Jones and was born in 1892. He made his MLB debut in 1914, for the Cleveland team known as the Naps in Napolean Lajoie's last season before returning to Philadelphia. He pitched one more season for the Indians before being traded to the Boston Red Sox in the deal that sent Tris Speaker to the Indians. Over his first 4 seasons, he would get into just 70 games total, just 10 of them as a starting pitcher. But in 1918, he finished 16-5, 2.25 and pitched in the 1918 World Series when the Red Sox beat the Chicago Cubs. He joined the Yankees in 1922 and pitched for them as they won the AL Pennant in 1922 (their second in a row), the World Series in 1923 and for the team that won the AL Pennant in 1926. Jones had some very good seasons, but for the most part, was slightly above average. He won 20 games twice, but also lost 20 games twice. He was an AL League Leader just 4 times in his 22 year career. In 1918, he led the league with his .762 winning percentage. In 1919, he led the league in earned runs allowed with 102. In 1925, he led the AL in losses with 21 and in 1930, he led the league with his 0.2 HR per 9 innings pitched (just 4 HR given up that season). He was a durable pitcher, but pitched to contact. He finished his career with a 229-217 career record, and though he has recorded more wins than some Hall of Fame pitchers, he will probably never get in.
The other Samuel Jones was actually born Daniel Pore Franklin in either 1923 or 1925. Also known as "Toothpick Sam", Jones was signed by the Cleveland Indians in 1950 after playing from 1946-1948 in the Negro Leagues. This Sam Jones was more of an intimidating pitcher, as he had the propensity for walking a lot of batters as well as getting a lot of strikeouts. Like the older pitcher, Jones made his debut with the Cleveland franchise pitching in 1951 and 1952. He would pitch 1953 and 1954 in the minors before the Cubs acquired him in a trade for Ralph Kiner. In his first full season, in 1955, he led the NL in losses (20), walks (185) and hit by pitches (14). However, he did lead the NL with his 198 strikeouts as well as lowest hits per 9 IP (6.5) and Ks per 9 IP (7.4). Two of the next three years, Jones would lead the NL in both walks and Ks and in 1958, he led the NL with 21 wins and a 2.83 ERA. He would pitch in two All Star Games (in 1955 and 1959).
The two pitchers really were very different. They both broke in with Cleveland and both briefly pitched in St Louis and Chicago, but Sad Sam pitched for the White Sox and Browns while Toothpick pitched for the Cardinals and Cubs. The original Sad Sam pitched his entire 22 year MLB career in the American League. The latter one spent 8 seasons in the NL and 4 in the AL. "Toothpick Sam" was certainly more intimidating and dominant at his best. He also lost a couple seasons because of the start of integration. He also never got a chance to pitch in the postseason, mostly because he was in the wrong place in the wrong time. He was a member of the Cleveland Indians in 1951 and 1952, while they won the World Series in 1948 and the AL Pennant in 1954. In 1954, the Indians lost to the New York Giants, where Jones would join in San Francisco for 1958 and 1959. He pitched for the Cardinals in the 1950s and for Detroit and Baltimore before they started winning again.
They both had distinct careers, as the latter won 102 games and lost 101. Neither were great but both were useful MLB pitchers. They combined to pitch 34 years in the big leagues. Sad Sam would die in 1966 at age 73, while Toothpick Sam would pass away in 1971 at age 45. Amazing how they were born 33 years apart, but died just five years from each other.
Two interesting things regarding common teammates. The earlier Sam Jones was teammates with Babe Ruth with the Red Sox from 1916-1919 and with the Yankees from 1922-1926. The later one was teammates with catcher Hobie Landrith in 1956 with the Cubs, 1957 and 1958 with the Cardinals, 1959-1961 with the Giants and 1964 with the Orioles.