Dennis Bennett was born in Oakland, California, on October 5, 1939. He was a fun-loving character on baseball’s stage for much of the 1960s, was blessed with a great left arm and a thirst for the good life. He also overcame several reckless brushes with danger, including a tragic accident, to forge a seven-year big-league career, though not reaching the heights he likely could have.

He played Little League and Babe Ruth League baseball before entering high school. At Yreka Union High School, he lettered in baseball, basketball, track, and football. In his senior year, he won 15 of 16 decisions on the mound and hit .458, playing first base when not pitching. 

His off-the-field activities in his youth were atypical. Firefighting was a vital and lucrative occupation in his region, so he often skipped school to go off and join a fire crew (lying about his age). If that wasn’t dangerous enough, he and some friends made extra money in the summers traveling around Northern California to various rodeos, riding saddleback and bareback bronco events. 

Bennett did not throw particularly hard as a teenager, and few scouts showed any interest in watching the hurler. He garnered a partial scholarship to pitch for Mount Shasta Junior College, pitching a single season for its baseball team. At that point, he was offered a contract by the Philadelphia Phillies. He was no bonus baby and would get $500 if he stayed in the organization for 90 days, and $250 a month.

Bennett’s professional career began in Johnson City, Tennessee, in the Appalachian League. The next year he pitched for Bakersfield in the California League, before spending the 1960 campaign with Asheville, North Carolina (South Atlantic League).

He spent the start of 1961 in Chattanooga before tearing up his knee. The circumstances surrounding the injury typify the personality of Bennett, always a free spirit. He took part in a somersault race downhill and jammed the cartilage in his knee. An operation ended his season. He told his manager he got hurt jogging in the outfield.

The next spring he was invited to major-league camp, likely because the Phillies wanted to see how his knee was. Not only was his knee fine, the rest had added several miles per hour to his fastball. He was sent to Triple-A Buffalo (International League), before his recall to Philadelphia in May.

His first major-league appearance took place at Chicago’s Wrigley Field on May 12, 1962. After three mediocre starts, his first major-league victory was a four-hit shutout that snapped the Los Angeles Dodgers’ 13-game winning streak on June 2nd.

The Phillies sent him to Arecibo, Puerto Rico, that winter to get ready for 1963. Dennis had acquired a reputation as a free spirit, who enjoyed the nightlife. He was single and spent his evenings doing what single men are wont to do. He was involved in a car accident that killed the driver. Bennett was thrown through the windshield, breaking his left ankle, pelvis, and left shoulder blade, and leaving severe lacerations all over his face. He had been sitting with his back against the door and leg up on the seat, talking to the people in the rear seat. After months in the hospital, he was working out by the end of May and, miraculously, joined the Phillies in late June. For his efforts he won a local award as the most courageous athlete on the team. 

Bennett started strong in 1964, winning eight of his first 12 decisions through June. In the second half of the 1964 season, his shoulder, and its still undiagnosed injury, started to bother him and the pain never really went away again. By season’s end the pain in his shoulder was constant and tremendous. The 1964 Phillies were one of the more famous teams in Philadelphia history, and Bennett’s injury was likely the biggest cause of their collapse. 

In November the Phillies dealt Bennett to the Boston Red Sox for slugger Dick Stuart. He was angered by the deal because he felt the team had promised him he would be back with the club. More than that, he knew he was hurt and felt the Phillies knew it. When he was speaking at a banquet in Boston that winter, he surprised the assembled media and team personnel when he casually mentioned that his sore arm might not be ready for the opening of the season. The Phillies offered to nullify the deal, but the Red Sox were happy to be rid of the enigmatic and controversial Stuart and left it alone.

Bennett pitched adequately for the 1965 Red Sox, starting 18 games and relieving in 16 others, finishing 5-7 for a team that lost 100 games. He started the season on the disabled list, joining the club in early May. 

But his reputation for zaniness grew. For one thing, he carried several guns with him on the road, and often on his person. Then there was the time he shot out the lights in his hotel room, to save getting up and turning the switch.

After the 1965 season he finally underwent shoulder surgery, which kept him on the disabled list until mid-July. A doctor finally isolated the problem. There was calcium had built up in a crack in the shoulder blade caused by his 1963 accident. Upon his return, he was actually one of the more steady members of the rotation, finishing 3-3 with a 3.24 ERA in 13 starts for an improving club that played .500 ball in the second half.

The next spring he was involved in an incident in Florida that was part of a sad lineage of race relations with the Red Sox. He entered a club in Lakeland with pitchers Dave Morehead and Earl Wilson. While he and Morehead were asked for their drink orders, the bartender turned to Wilson, an African-American, and said, “We ain’t serving you. We don’t serve niggers here.” The players left, but word of the incident soon leaked out.

Bennett later related how lax Red Sox mangement was in 1966: “You’d have four or five players and some girls, and you’d throw a party. And it might go until six, seven in the morning, and maybe you had a day game that day. And the thing was, you’d get on the bus, and manager Billy Herman would be sitting in the front seat, and everybody would talk about the party the night before, and Billy would sit there hearing it all, but there wasn’t too much he could do about it because some of the stars were the ones doing the talking. He didn’t have any control over the ball-club whatsoever.”

The new manager for 1967, Dick Williams, was different. When Bennett and another pitcher showed up late one day in the spring, Williams publicly called them out and fined them. He continued to pitch well early in the 1967 season and on May 1st in Anaheim, shut out the Angels with a six-hitter, and also hit a three-run home run. He was doubly happy about the shutout, as the local writers had promised him a champagne party. They came through, holding it at the Playboy Club in Boston. But his relationship with Williams deteriorated further. On June 24th the Red Sox traded Bennett to the Mets. Williams had not spoken to him in a few weeks prior to telling him he had been dealt.

Bennett wasn’t through pitching just yet. He spent the next five years in the Pacific Coast League, much of it far removed from the continental United States. He played for Hawaii in 1969 and 1970. He spent a year and a half with Salt Lake City before returning to Hawaii for parts of the 1972, and 1973 seasons. At the conclusion of the latter campaign, he finally walked away from the game.

Having settled in Klamath Falls, Oregon, Bennett operated a restaurant and bar for a few years, worked for several years in a mill, operated another bar, and finally opened a more elaborate club with banquet rooms in 1998. In 2010 he and his wife owned a four-story commercial building in town that housed a boutique, an interior decorator shop, and a hall for banquets and parties. His businesses and big family kept him at home most of the time, but he attended many reunions and fantasy camps over the years. 

Dennis Bennett passed away on March 24, 2012 at home in Klamath Falls, surrounded by friends and family.