Chatham Anglers

In 1923 the Cape Cod Baseball League was formed and included four teams: Chatham, Falmouth, Osterville, and Hyannis.[2] This early Cape League operated through the 1939 season and disbanded in 1940, due in large part to the difficulty of securing ongoing funding during the Great Depression.[3][4] Chatham competed in the Cape League from the league's inaugural 1923 season through the 1926 season, then from 1927 to 1929 competed as a combined Chatham-Harwich team with home games split between Veterans Field and Harwich's Brooks Park.[5][6][7]

Veterans Field has been home of Chatham baseball since the 1920s.

Chatham's 1923 team included CCBL Hall of Famer Merrill Doane. Doane, a 1924 graduate of Chatham High School, remained involved in the Cape League and Chatham baseball for over 60 years. One of the longest-tenured general managers in Cape League history, Doane was instrumental in the league's transition to an NCAA-sanctioned collegiate league in the early 1960s, and helped build the powerful Chatham teams of the 1960s.[8] In 1925, Brockton High School star Pat Creeden played third base for Chatham, and went on to play briefly for the Boston Red Sox in 1931.[9][10]

In the 1927 season, the combined Chatham-Harwich team finished fourth in the five-team league, but nevertheless was described as "the hardest hitting team in the league."[11] 1927 Chatham-Harwich first baseman Jack Burns went on to play in seven major league seasons for the St. Louis Browns and Detroit Tigers.[12][13][14][15] In all three seasons of the joint Chatham-Harwich team, the club featured Boston College batterymates pitcher Pete Herman and catcher George Colbert, as well as flashy infielder Artie Gore. The trio of Herman, Colbert and Gore later teamed up again with Barnstable to bring that club multiple Cape League championships in the 1930s.[16][17] Gore went on to a major league umpiring career, working ten years in the National League, including two World Series assignments.

In 1930, Chatham again fielded its own team, as Harwich split off and became a separate club. Pete Herman remained with the Chatham team as its player-manager in 1930 and 1931, leading the team on an exciting stretch run and second-place finish just two games behind pennant-winning Wareham in 1930.[18][19]

Chatham withdrew from the league prior to the 1932 season as a result of the town's decision not to appropriate funds for the team.[20] Throughout the rest of the 1930s, Chatham's town team competed in the Cape Cod Twilight League, winning that league's title seven consecutive seasons from 1933 to 1939.[21]

Artie Gore was a flashy infielder for Chatham-Harwich from 1927 to 1929, and went on to a ten-year umpiring career in the National League.

After a hiatus during the years of World War II, the Cape League was reconstituted in 1946, with Chatham joining the Lower Cape Division.[22] Chatham has been a member of the Cape League ever since.

CCBL Hall of Fame skipper John Carroll took the helm at Chatham in 1961.[23] The following season, Carroll's club finished the regular season in first place atop the Lower Cape Division, but failed to reach the Cape League title series, losing to Harwich in the Lower Cape championship series.[23][24]

In 1963, the CCBL was reorganized and became officially sanctioned by the NCAA. The league would no longer be characterized by "town teams" who fielded mainly Cape Cod residents, but would now be a formal collegiate league. Teams began to recruit college players and coaches from an increasingly wide geographic radius.[25]

The league was originally composed of ten teams, which were divided into Upper Cape and Lower Cape divisions. Chatham's team, known as the Chatham Red Sox,[26] joined Orleans, Harwich, Yarmouth and a team from Otis Air Force Base in the Lower Cape Division.

Chatham continued to be managed by John Carroll, whose 1963 club featured CCBL Hall of Famer Ken Voges of Texas Lutheran University, who led the league with an astronomical .505 batting average.[27] The Red Sox finished the regular season with a 28–6 record, good enough for first place in the Lower Cape Division, but fell to Orleans in the playoffs.

Thurman Munson led Chatham to its first CCBL championship in 1967.

Chatham continued its regular season dominance in 1964, 1965 and 1966, finishing atop the Lower Cape Division each year, but falling in each season's CCBL title series. The 1964 team was piloted by Bill "Lefty" Lefebvre, who had played in the Cape League for Falmouth in the 1930s, and had later played in the major leagues with Boston and Washington.[28][29] Lefebvre's team featured CCBL Hall of Fame second baseman Steve Saradnik of Providence College, who batted .314,[30] and pitcher Charlie Hough, who went on to a 25-year major league knuckleballing career.

In 1965, Lefebvre was succeeded by CCBL Hall of Fame manager Joe "Skip" Lewis, who led the team through 1969.[31][32][33] Lewis' 1965 squad returned Saradnik, and added another two CCBL Hall of Famers in University of Connecticut righty Ed Baird, who posted a 3–0 record with a 0.45 ERA,[34] and George Greer, who batted .349 and led the league in doubles and triples.[35]

The star-studded 1966 Chatham team returned Saradnik, Baird and Greer,[36][37] and added another three CCBL Hall of Famers: catcher Tom Weir, who led the league with a .420 batting average,[38] all-star hurler Joe Jabar, who went 7–0 with a 1.53 ERA and took home the league's Outstanding Pitcher Award,[34] and Pittsfield, Massachusetts native Tom Grieve. Drafted out of high school in the first round, sixth overall, of the 1966 Major League Baseball draft by the Washington Senators, Grieve played in 25 games for Chatham and batted .416 prior to signing with Washington and moving on to a lengthy major league career.[38]

In 1967, it finally came together for Lewis' boys. Saradnik, Greer, Baird and Jabar all returned and were hungry for a title.[39] Added to the mix was Kent State University catcher Thurman Munson, who hit .420 on the season and was named league MVP. During the regular season, Chatham pitcher Don Gabriel tossed a no-hitter against Harwich at Veterans Field.[40] Chatham again finished in first place in the Lower Cape Division,[41] and met Upper Cape powerhouse Falmouth for the second consecutive season in the title series. In Game 1 of the championship, Chatham pitcher John Frobose twirled 13 innings in a game that was called due to darkness and ended in a 1–1 tie. Chatham took Game 2, 7–1, behind the stellar pitching of Baird. Jabar, the league's Outstanding Pitcher, was the star of Game 3, tossing a complete game five-hitter, and knocking in the game-winning RBI in Chatham's 3–2 victory, clinching the series and giving Chatham its first Cape League championship.[42][43][44]

Munson went on to be selected by the New York Yankees in the first round, fourth overall, of the 1968 Major League Baseball draft. A perennial all-star for the Bronx Bombers, Munson won two World Series and was named the Yanks' first captain since Lou Gehrig. His tragic 1979 death brought fond reminiscences from those who knew him at Chatham.[45] Munson was inducted into the CCBL Hall of Fame as part of its inaugural class of 2000, and his name graces the league's annual award for batting champion.[46]

CCBL Hall of Famer Mike Stenhouse played for Chatham in 1977, '78 & '79.

In the late 1960s, Chatham had dropped the nickname "Red Sox", and reverted to the colloquial Chatham Townies moniker of earlier years. In 1972, the Chatham Athletic Association settled on Chatham Athletics as the team's new moniker, and the Chatham A's were born.[47] The A's finished the 1973 regular season in first place atop the Cape League under skipper Ben Hays. The team featured future major leaguer Dave Bergman, the CCBL batting champ who hit at a .341 clip, and CCBL Hall of Fame hurler John Caneira, the league's Outstanding Pitcher, who posted a 9–1 record and led the league with a 1.37 ERA while striking out 118 and walking only 23 in 92 innings.[48]

CCBL Hall of Fame manager Ed Lyons took the reins in 1976, and led the A's to another first-place finish.[46] Chatham was led by the league's Outstanding Pro Prospect Steve Taylor, and CCBL Hall of Famer Mickey O'Connor, a 6-foot-6 southpaw who went 9–0 with a 1.07 ERA and eight complete games, and was the league's Outstanding Pitcher.[8] The team ousted Hyannis in the playoffs,[49] but was shut down by Wareham in the title series.[50] Lyons skippered the Athletics for seven seasons, with the team qualifying for postseason play in six of the seven years.

The A's of the late 1970s featured Jim Lauer, who set a CCBL record with three home runs in a single game against Hyannis,[51] Harvard University slugger and CCBL Hall of Famer Mike Stenhouse, who starred for Chatham from 1977 through 1979,[52] and longtime major league hurler and CCBL Hall of Famer Walt Terrell, who went 9–4 with a 2.20 ERA in 1979 while working a league record 122.2 innings on the season.[30]

Lyons again skippered Chatham to a first-place finish in 1980 before succumbing to Falmouth in the championship series.[53] The 1980 A's starred CCBL Hall of Famers Glenn Davis, who batted .377 on the season, and Jim Sherman, who batted .339 and returned to Chatham in 1981 and enjoy another all-star season, batting .335.[23][54]

Kevin Seitzer hit .677 in the playoffs for Chatham's 1982 CCBL title team.

In 1982, skipper Ed Lyons announced mid-season that he would be retiring after the summer.[55] Lyons had managed six seasons at Wareham in the early 1970s, and was now in his seventh season with Chatham, but had yet to win a league title. Lyons' 1982 A's finished the regular season in fourth place with a pedestrian 20–21–1 record, having slipped into the playoffs on the final day of the season with a victory over Orleans. The team starred future major league all-star Kevin Seitzer, who hit .291 on the season and .677 in the playoffs, slugger Billy Merrifield, who clouted eight homers on the season, team MVP Brett Elbin, all-star centerfielder Greg Schuler, and the league's Outstanding Pro Prospect, pitcher Gary Kanwisher, who led the league with a 1.57 ERA. Lyons' staff included young third base coach John Schiffner. The A's matched up against first place Wareham in the playoff semi-finals, and promptly disposed of the Gatemen in two games.[56]

In the championship series, Chatham met up with Hyannis in a best three-out-of-five title tilt. The A's went on the road for Game 1, and came away with a tight 5–4 win in 11 innings. Game 2 at Veterans Field also went to extra frames, with the Mets taking a 4–3 lead in the 11th, but the home club tied it in the bottom half, and then took the lead in the 12th to win by another 5–4 tally. Reliever Kurt Lundgren got the win in both games, coming on in the eighth inning of Game 1, then in the 12th inning of Game 2 to nail it down after starter Kanwisher held the mound through eleven.[57] After two nail-biters, Game 3 at McKeon Park was a runaway. The A's led off the game with a dinger by Elbin and another by Merrifield, scoring four runs in the first for starter Jeff Brewer, and never looked back. Brewer tossed a complete game four-hitter, and the A's pummeled the Mets, 9–0, to complete the three-game sweep and claim Chatham's second league crown.[58][59][60]

In 1983, A's slugger Bob Larimer tied a league mark by crushing three home runs in a single game; his feat demonstrated power to all fields as his trio of clouts against Falmouth left the yard in left, center, and right fields respectively.[51] Chatham boasted the league MVP in 1984, as CCBL Hall of Famer Joey Cora was the A's all-star second baseman, batting .373 and leading the league with 28 stolen bases.[61] The 1985 A's returned to the league championship series behind the play of CCBL Hall of Famers Tim McIntosh and Mark Petkovsek, but were shut down by Cotuit. McIntosh led the league with a .392 batting average,[61] and Petkovsek went 7–1 for the A's and returned to Chatham the following season to win another seven games.[62]

The late 1980s saw a pair of future major league sluggers in the Chatham lineup. Albert "Joey" Belle played for the A's in 1986, and went on to crush 381 major league homers. Jeff Bagwell spent the summers of 1987 and 1988 in Chatham. He struggled in his first season, but followed up with an all-star 1988 campaign in which he hit .315 with a .449 on-base percentage, and went 4-for-4 with a home run in the CCBL All-Star Game. Bagwell was inducted into the National Baseball Hall of Fame in 2017, the fifth former Cape Leaguer to be so honored.[63][64]

Baseball Hall of Famer Jeff Bagwell played for Chatham in 1987 and 1988.

Chatham was one of the league's most successful teams throughout the 1990s, finishing in first place atop the East Division five times, qualifying for the playoffs in eight of the ten years, reaching the league championship series six times, and taking home three CCBL crowns.

Skipper Rich Hill's 1992 Chatham squad posted an impressive 31–11 regular season record, and featured ace reliever Scott Smith and CCBL Hall of Fame hurler Steve Duda. Duda had pitched for the A's in 1991, posting a 4–4 record and tossing a no-hitter against Y-D. He was even better in 1992, going 6–1 with a 0.90 ERA.[65][66] Duda led the A's into the 1992 playoffs against Brewster by tossing a complete game in Chatham's 4–2 Game 1 victory. The A's completed the sweep of the Whitecaps with a 1–0 victory in Game 2 to secure Chatham's spot in the league title series against Cotuit.[67]

The A's took Game 1 of the 1992 championship series at Veterans Field, powered by a two-run blast by Mike Smedes. Game 2 at Lowell Park was an all-time classic. The game went into the 12th inning tied at 2–2 thanks to 11 stellar innings by A's starter Duda, who threw 125 pitches on three days' rest, and appeared to get stronger as the game moved along. Chatham played small-ball in the top of the 12th, pushing across Jeremy Carr, who had walked and reached third on a stolen base and a Cotuit error, then scored on a Brian Garrett single. Smith came on in relief of Duda in the bottom of the frame, and set down the Kettleers in order to clinch the series for the A's and secure Chatham's third CCBL title, with Duda taking home playoff MVP honors.[68][69][70]

Midway through the 1993 season, manager Rich Hill left to take a head coaching job at the University of San Francisco, and assistant coach John Schiffner took the helm at Chatham.[71] Schiffner, who had been Hill's assistant since 1990, had played in the CCBL for Harwich from 1974 through 1976, and had served previously as Chatham assistant coach from 1978 to 1982. He went on to pilot Chatham for a league record 25 years, and was inducted into the CCBL Hall of Fame in 2018.[72] Schiffner's 1994 squad featured CCBL Hall of Famer Mike Lowell, an all-star second baseman who hit .307 for the A's.[73] Lowell went on win World Series MVP honors with the 2007 Boston Red Sox. In 1995, Schiffner took the club to the CCBL title series, but lost to Cotuit.[74]

Brian Roberts played shortstop for Chatham's 1998 CCBL title club.

In 1996, Chatham featured the league's Outstanding Pro Prospect, fireballing reliever Matt Anderson, but the team struggled early on, losing eight in a row at one point. The A's finished the regular season a hair over the .500 mark, and met first place Brewster in the East Division playoffs. In Game 1, Chatham's Matt Purkiss clobbered a two-run homer in the third and ace Keith Evans worked 11 innings allowing only four hits as the A's and Whitecaps took a 2–2 tie into the 12th. In the top of the 12th, Chatham's Scott Friedholm smashed a three-run homer to left, and Anderson came on in the bottom half of the frame to nail down the victory. Chatham completed the sweep with a 3–0 win in Game 2 on the strength of second baseman Jermaine Clark's two-run double, and advanced to the title series against Falmouth.[75]

The 1996 championship series opened at Guv Fuller Field, with Chatham catcher Scott Fitzgerald stifling the Falmouth attack early on in Game 1, cutting down three stolen base attempts in the first three innings. Chatham pushed across three runs playing small-ball and A's starter Seth Etherton was masterful, twirling eight shutout innings and striking out 14 before turning it over to Anderson for the ninth-inning save in the A's 3–0 win. Evans took the mound for the A's in Game 2 at home and followed up his 11-inning semi-finals outing with a complete game gem. Clark, whom Schiffner described as the team's spark plug all season,[76] went 3-for-4 with a pair of doubles to go with his usual stellar work in the field, and the A's downed the Commodores, 6–2, for the title. Evans and Clark shared playoff MVP honors as Chatham sealed its fourth Cape League championship and its first to be clinched at Veterans Field.[77][78]

Schiffner's 1998 club was loaded with talent. Slugger Matt Cepicky was a .327 hitter who won the All-Star Game Home Run Derby, and took home East Division MVP honors in the East's 3–2 All-Star Game victory at Veterans Field.[79] In addition to Cepicky, the A's boasted an abundance of top moundsmen. 6-foot-8 righty Kyle Snyder was the league's Outstanding Pro Prospect, Tim Lavigne was the Outstanding Relief Pitcher, and CCBL Hall of Famer Rik Currier had an all-star season, posting a 5–2 record with a 2.37 ERA.[66] After sweeping Brewster in the playoff semi-finals, the A's met Wareham in the best-of-five championship series.

Snyder started Game 1 of the 1998 title set for Chatham at Clem Spillane Field, but got roughed up by the Gatemen, who took the opener, 6–4.[80] The A's held serve in Game 2 at Chatham as Jeremy Wade tossed a complete game five-hitter in the home club's 5–1 victory. Game 3 at Wareham was a classic pitcher's duel as Currier was matched up against CCBL Hall of Famer and future major league all-star Ben Sheets for the Gatemen. The game remained scoreless until the bottom of the 14th when the Gatemen walked off with the game's only run. The A's evened the series again in Game 4 at home, taking the lead in the bottom of the eighth on RBIs by Ryan Earey and Barry Gauch, and hanging on to win, 4–3.[81] Behind the solid mound-work of Devon Nicholson, Chatham clung to a 3–1 lead through seven in a tense Game 5 finale that saw Gatemen skipper Don Reed tossed in the seventh. The A's broke it open in the eighth on a Brian Peterson two-run double, and tacked on another to make it a 6–1 title-clinching win. Cepicky, who went 12-for-32 with six RBI in the playoffs, shared MVP honors with Earey, who was strong in two relief appearances on the hill while going 3-for-10 at the plate.[82][83]

The 1999 A's enjoyed a 30-win season and finished first in the East Division, falling to Cotuit in the championship series.[84] The team returned Currier who had another brilliant season, posting a 7–0 record with a 1.34 ERA, and being named the league's Outstanding Pitcher. Currier was joined on the staff by CCBL Hall of Famer Derrick DePriest, who did not allow an earned run in 22.2 innings of work, and was named the league's Outstanding Relief Pitcher.[52]

Evan Longoria was CCBL MVP for the A's in 2005.

The early 2000s saw a pair of CCBL Hall of Fame relievers take the mound for Chatham. Hard-throwing righty David Bush posted a 0.84 ERA and led the league with 11 saves in 2000, then returned in 2001 to record an even stingier 0.34 ERA.[73] Fireballer Zane Carlson spent three sparkling seasons with the A's from 2001 through 2003. He earned 12 saves in each of his first two years, and 10 more in his third, with a combined three-year ERA of 2.23.[85][33] Bush and Carlson led the 2001 squad to the CCBL championship series, but the team was defeated by Wareham.[86][87]

Former A's manager Ed Lyons was honored by the team in 2001, as the 1982 title-winning skipper's uniform number "29" became the first number to be retired by the franchise.[88] In 2006, the team paid the same honor to longtime assistant coach Matt Fincher, retiring his number "23".[89]

The 2005 A's boasted a wealth of talent, as CCBL batting champion Chris Coghlan[90] was joined by future major league all-stars Todd Frazier,[91] CCBL MVP Evan Longoria,[92][93] and second-year Chatham hurler Andrew Miller, the CCBL's Outstanding Pitcher and Outstanding Pro Prospect, who was inducted into the CCBL Hall of Fame in 2012.[94][23]

In late 2008, Major League Baseball announced that it would enforce its trademarks, and required those CCBL teams who shared a nickname with an MLB team to either change their nicknames or buy their uniforms and merchandise only through MLB-licensed vendors. Chatham opted to drop its "Athletics" moniker, and became the Chatham Anglers, a name which celebrated the town's nautical heritage and allowed for continued use of the "A's" nickname. The team also retained its uniform colors and pinstripe pattern.[95][96]

2011 Angler Kris Bryant

The Anglers qualified for postseason play in seven of ten years in the 2010s, but remained in a championship drought for a second consecutive decade. The 2011 Anglers featured future major league all-star and National League MVP Kris Bryant[97] and CCBL Home Run Derby champ Richie Shaffer.[98] In 2013, the Anglers finished in first place atop the East Division, and starred the CCBL's Outstanding Pitcher, Lukas Schiraldi,[99] and all-star infielder J. D. Davis, who took home All-Star Game MVP honors for the East Division for his double and three-run homer in the East's 9–4 victory.[100]

Chatham boasted the CCBL's Outstanding New England Player in consecutive seasons in 2013 and 2014. West Haven, Connecticut's Tommy Lawrence of the University of Maine took home the honors in 2013 after a stellar season in the Chatham bullpen. Lawrence posted a 3–0 record with a 1.58 ERA, striking out 23 and walking just a single batter in 28 1/3 innings.[101] The following summer, it was Lexington, Massachusetts native and Boston College slugger Chris Shaw. Shaw clubbed seven dingers to lead the league for Chatham in 2014, and finished second in the league with 31 RBIs.[102]

Manager John Schiffner stepped down after the 2017 season, having held the post for a league record 25 summers.[103][104][105] In 2018, first-year skipper Tom Holliday[106] led the Anglers to the league championship series, where they were downed by Wareham.[107][108] Holliday's club finished first in the East Division in 2019, but was bounced from the playoffs by Harwich.[109]

The 2020 CCBL season was cancelled due to the coronavirus pandemic.[110]

Chatham missed the CCBL Playoffs in each season 2021 to 2023, marking the first time since the league moved to an eight-team playoff format that the Anglers failed to qualify for the postseason in three consecutive seasons.

The 2023 season saw the end of the Holliday era after Chatham's skipper was forced to resign mid-season due to "personal health reasons."[111][112] Assistant coach Marty Lees was named acting manager on July 12, and led the team to a 3-11-1 record before stepping down to accept a job as head coach at Stillwater High School.[113][114][115] Assistant coach Todd Shelton was named interim manager on July 28, and led the team to a 5-1 record over its final six games, highlighted by a four-game winning streak to end the season.[116][117]

On August 21, 2023, Georgia Gwinnett College head coach Jeremy "Sheets" Sheetinger was named the 13th manager in Chatham history.[118]

* There were no postseason playoffs during the period 1923–1931. The regular season pennant winner was simply crowned as the league champion.
^† Played from 1927 to 1929 as combined "Chatham-Harwich" team

* Regular seasons split into first and second halves are designated as (A) and (B).

Chatham boasts one of the winningest managers in Cape Cod Baseball League history in John Schiffner, affectionately known as "Schiff" across amateur baseball. Schiffner retired after his 25th year managing the Chatham A's in 2017, and served as either the team's manager or an assistant coach for 34 total seasons. Schiffner joined legendary Chatham manager Ed Lyons as an assistant coach just two years after graduating from Providence College. While at Providence, Schiffner had spent three summers playing in the Cape League for the Harwich Mariners from 1974 to 1976. After being drafted and playing part of a minor league season in the Pittsburgh Pirates organization in 1977, Schiffner returned to the Cape as an Assistant Coach in Harwich for the summer. During the 1977 playoffs, A's Manager Ed Lyons approached Schiffner and invited him to join his staff for the following summer, and Schiffner quickly accepted the offer.

Matt Harvey pitched against Coach Schiffner in high school, then played for him in Chatham

Schiffner served as an Assistant Coach under Lyons in Chatham from 1978 to 1982, then returned in 1990 in the same role after a stint scouting for the Montreal Expos. Schiffner became the Chatham A's manager on July 7, 1993, when manager Rich Hill accepted the head coaching position at the University of San Francisco and took his new post immediately. Schiffner took over a last place team more than halfway into the season, but oversaw a stunning 16-7 record down the stretch as the A's claimed a first-place finish and Schiffner was offered the position of manager on a permanent basis, a major breakthrough for him after a significant number of unsuccessful managerial interviews in Chatham and elsewhere around the Cape League in previous years.

Including that 1993 campaign, Schiffner managed the A's for 25 years, stepping down at the end of the 2017 Cape Cod Baseball League season. He managed the A's to CCBL championships in 1996 and 1998, and became widely regarded as the face and voice of Cape Cod Baseball.

Schiffner announced that the 2017 season would be his last after a Chatham Anglers game in Harwich in July 2017. Soon after, he revealed that he was leaving Chatham to become an assistant coach at the University of Maine, where he would work with new Maine head coach Nick Derba, the catcher of the powerful 2005 Chatham A's team and one of Schiffner's favorite former players. Schiffner had previously served as the volunteer assistant coach at Maine during the 2013 season, when Derba was the Black Bears' hitting coach under current Stetson University head coach Steve Trimper. On August 10, 2017, the Chatham Athletic Association announced that former Oklahoma State University head baseball coach Tom Holliday would succeed Schiffner, beginning with the 2018 Cape Cod Baseball League season.

Schiffner also served as the head baseball coach for 33 years at Plainfield High School in Plainfield, Connecticut, where he also taught history for over three decades. He is the winningest coach in Connecticut state high school baseball history, and often spotted future Cape League talent on high school fields across the state, including current Major League pitchers Matt Harvey and Dominic Leone, both of whom pitched against Schiffner's teams in high school and went on to play for him in Chatham before reaching the Majors. Schiffner was inducted into the Connecticut High School Coaches' Association Hall of Fame in November 2017.[105]

Following Schiffner's retirement after the 2017 season, Tom Holliday, the 64-year-old former Oklahoma State head coach, was named Chatham's manager.

Holliday took the league by storm in 2018, guiding Chatham to a first-place regular season and its first CCBL Championship Series appearance in 17 seasons. The 2018 team, headlined by Spencer Torkelson, Alek Manoah, Blake Sabol, Greg Jones, Austin Bergner, and Ty Madden, fell to the Wareham Gatemen, two games to none, in the title series.

In 2019, Holliday again skippered the As to a first-place finish in the East Division, but his team was swept out of the playoffs by Harwich in the first round.

In 2020, when the Cape League canceled its season due to the COVID-19 Pandemic, Holliday managed the Tulsa Drillers of the Texas Collegiate League.[231]

Holliday returned to Chatham when the CCBL resumed action in 2021, but his team never qualified for the playoffs again. Across the 2021, 2022, and 2023 seasons, Chatham complied a record of 46-66-14, finishing in fourth or fifth place in the East Division each time.

Holliday's coaching staffs, in contrast to Schiffner's, often featured notable former college and professional baseball figures, including Dennis Cook, Jay Powell, Mickey Tettleton, Rusty Greer, and Marty Lees.

During his tenure as Anglers manager, Holliday was known for his affection for junior college and community college players, his tendency to recruit Oklahoma State players who played for his son Josh Holliday, and his no-holds-barred interviews with broadcasters Josh Schaefer, Emmanuel Berbari, and Joe Puccio.

On July 12, 2023, Holliday resigned as Anglers manager with 23 games left in the season, citing “personal health reasons.” Assistant coaches Marty Lees and Todd Shelton managed the team for the balance of the season. On August 21, the Chatham Athletic Association announced that Georgia Gwinnett College head baseball coach Jeremy "Sheets" Sheetinger would take over as Anglers manager, beginning with the 2024 Cape Cod Baseball League season.[232]

Freddie Prinze Jr., star of the movie Summer Catch

The Chatham A's were featured prominently in the 2001 Warner Bros. motion picture Summer Catch, starring Freddy Prinze Jr. and Jessica Biel, a comedic sports movie depicting fictional ballplayers spending a summer in Chatham filled with baseball and booze. Though the movie is an extreme fictionalization, some of the fictional players are loosely based on past A's players, and real life A's manager John Schiffner is the fictional team's coach, as portrayed by actor Brian Dennehy. The majority of the movie was filmed in South Carolina, though small portions of scenic shots were taken in Chatham at Veterans Field. The A's actual logos, colors, and uniforms are used in the movie, along with loose copies of other Cape Cod Baseball League team names, logos, and colors.

Jim Collins' The Last Best League (2004, ISBN 0-306-81418-8) is a non-fiction account of the 2002 Chatham A's, which featured infielder Jamie D'Antona and manager John Schiffner as the book's protagonists. Collins follows and recounts every move the players, coaches, fans, and others make in the ethnographic account of the full 2002 Cape Cod Baseball League and Chatham A's season. The book delves deeply into the life and baseball journey of John Schiffner, who was already the longest-tenured manager in the league and the undisputed face of Cape Cod Baseball at the time of the book's writing, even though he still stood 15 years away from retirement. Schiffner and his longtime assistant coach Matt Fincher are profiled heavily in the book. Fincher was the longtime head baseball coach at University of South Carolina-Upstate.

D'Antona, a highly touted power hitter from Wake Forest University who quickly becomes Collins' primary player focus in the book, is depicted as a laid-back ballplayer whose potential is hindered by occasional lapses in judgment and lack of effort. Collins follows D'Antona extensively both on and off the field, including to his job at the Chatham Fish Pier, where D'Antona delivered fresh fish to businesses all over Chatham at the crack of dawn. Following a short Major League career and a stint playing professionally in Japan, D'Antona returned to Chatham as the Anglers' hitting coach in 2017, working under John Schiffner in his final season as A's manager.

The two members of the 2002 A's who went on to the longest professional baseball careers are Chris Iannetta and Tim Stauffer. A starting pitcher from the University of Richmond, Stauffer was the best pitcher on the 2002 A's and amongst the best in the entire Cape League that summer. He was selected fourth overall by the San Diego Padres in the 2003 MLB Draft based largely off his performance on Cape Cod, and pitched in the Major Leagues for 10 seasons. He appeared in 201 MLB games, posting a 3.97 career ERA before retiring after the 2015 season. Iannetta, a catcher who just completed his 12th Major League season in 2017, is not one of the predominant characters in The Last Best League. One of a select few freshman hitters in the Cape League, Iannetta struggled all summer at the plate after his first year at the University of North Carolina, and was not asked back to Chatham the next summer, according to Collins in the book. He was selected in the fourth round of the 2004 MLB Draft by the Colorado Rockies, and has played in over 1000 MLB games, including over 900 starts at catcher for four different teams.

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