Jesse Tannehill had a cup of coffee with Cincinnati in 1894 but returned to the National League in 1897 with the Pittsburgh Pirates.

Tannehill's first full year was non-descript (9-9, 4.25 ERA), but he emerged as a top hurler for the squad over the next five seasons.  The lefthander won at least 18 Games every year, with four of them exceeding 20.  Tannehill had an ERA under 3.00 all of those years, with an ERA Title in 1901 (2.18), the same season he led the NL in FIP (2.59).  

He jumped to the New York Highlanders of the American League in 1903, thus ending his run with Pittsburgh, leaving the team with a stellar 116-58 record with an ERA of 2.75.  Tannehill was also a competent fielder, sometimes playing in the Outfield, which the Pirates were fine with considering he was a decent batter.  Over 865 At Bats with Pittsburgh, Tannehill batted .277 with 96 RBI, a more than respectable metric considering he was primarily a Pitcher.

Andy Van Slyke began his career with the St. Louis Cardinals, where after four years, he was dealt to the Pirates.  It was a great move for Van Slyke, as his career took off at Three Rivers.

Van Slyke mostly in Centerfield, and in 1988, his second year with Pittsburgh, Van Slyke went to his first All-Star Game, led the NL in Triples (14), and set career-highs in Home Runs (25) and RBIs (100).  He won both the Gold Glove and Silver Slugger and was fourth in MVP voting.  

Van Slyke would struggle offensively the following year, but his defense remained an asset, and he continued to accumulate Gold Gloves in his trophy case, gaining five in total.  The Outfielder went to two more All-Star Games (1992 & 1993), and in 1992, he had his best season in Baseball when he led the league in Hits (199), Doubles (45), and batted a career-high .324.  Van Slyke again won the Silver Slugger, and as he did in 1988, he was fourth in MVP voting.  The Pirates went to three consecutive National League Championship Series (1990-92), and Van Slyke can take a lot of the credit.

Van Slyke left the Pirates for the Orioles as a Free Agent before the 1995 Season, but he was no longer an All-Star contender by this time.  He accrued 1,108 Hits, batted .284 with 127 Home Runs for Pittsburgh.

One of the most underrated Pitchers in Pirates history, John Candelaria, was on many good Pittsburgh teams, though most fans were focused on the offensive stars of the team.

Candelaria was in the Pirates organization for sixteen years, beginning as a Second Round Pick in 1972 until he was traded to the Angels during the 1985 Season.  First making the Pirates in 1975, the "Candy Man" was a regular starter the following year, throwing a no-hitter as a sophomore.  Statistically, his best season was 1977, where the southpaw led the NL in ERA (2.34) and BB/9 (2.0), won 20 Games, was fifth in Cy Young voting and was an All-Star.

Candelaria had a lot more good moments with Pittsburgh, helping them win the 1979 World Series, and having six more seasons where he had at least 11 Wins.  After he was traded in 1985, he returned briefly to close out his career in the 1993 season.

With the Pirates, Candelaria had a 124-87 Record, a 3.17 ERA, and fanned 1,159 batters.

Lloyd Waner was one of the most consistent slap hitters of his day, and though he was not a flashy player, you know what you were going to get, which was pretty damned good.

Waner debuted in 1927, and had there been a Rookie of the Year; he likely would have won it.  He batted a career-high .355, collected 223 Hits, and led the NL in Runs Scored (133).  Waner did not beat that Batting Average again, but he cracked .300 nine more times, had four 200-Hit years, and was the league-leader in Triples (20) in 1929.  

After his skills declined in the late 30s, he was traded to the Boston Braves in 1941 but returned in 1944 in a reserve capacity to close off his career.  Waner had 2,317 of his 2,459 Hits with Pittsburgh and batted .319 for the club.  Despite his great hitting, his lack of power and speed hamper his rank somewhat.

Waner entered the Baseball Hall of Fame in 1967 via the Veteran’s Committee.