Green With Envy: A Boston Celtics Podcast

25 Years, 25 Celtics: The Quarter Century Boston Celtics Draft

Date: September 17, 2025
Hosts: Will and Greg
Guests (referenced): Mike Gorman, Drew Carter, Amina Smith, Dana Barros, others

Episode Overview

In this special episode, Will and Greg celebrate 25 years of Boston Celtics basketball since the turn of the century, spanning the 2000–2001 season through the 2023–2024 championship run. The hosts conduct a "Celtics Quarter Century Draft," each building a 12-man roster by selecting one Celtic per season—no player can be picked more than once, and only their contributions from that year count. The premise prompts nostalgia, tough choices, and debates over fan favorites, "what ifs", and franchise icons. Along the way, the duo reminisces on classic teams, painful seasons, championship highs, and the unique characters that have worn green.

Key Segments & Discussion Points

1. Concept & Rules of the Draft

[08:00]

• One player per season from 2000–01 to 2023–24.
• Once picked, a player is off the board.
• The version you select is for that year only (e.g., "2003 Paul Pierce" ≠ "2008 Paul Pierce").
• Roster must resemble a real NBA team using the All-Star structure: 2 guards, 3 frontcourt, 2G/3F/2 wildcards bench.
• Strategy: balance nostalgia, talent, positional needs, and fan favorites.

"The year is 2025. Quarter century—25 years of Celtics basketball... Let's look back in a fun way!" —Will [06:33]

2. Early 2000s: Pierce, Walker & That ‘What If’ Core

[09:25–17:34]

• Greg’s first pick: 2000–01 Paul Pierce, noting the infamous stabbing incident and his emergence as a star.

  "Although I'm getting him in the year he was stabbed and before his prime, I still think this version of Paul Pierce is the right pick." —Greg [11:18]

• Will follows: 2001–02 Antoine Walker, emphasizing his (sometimes inefficient) stat-stuffing prime and the fierce dynamic duo with Pierce.

  "Yo, we couldn't stop [Pierce and Antoine] because we doubled one, they just give the ball to the other dude." —KG (as recalled by Will) [16:33]

• Exploration of the ill-fated Joe Johnson trade, almost altering the franchise direction.

  "It seems crazy in retrospect...to trade a rookie that was showing a lot of promise." —Greg [14:12]

3. Mid-2000s: End of an Era and the Lost Years

[17:42–32:37]

• Walter McCarty, Tommy Heinsohn's cult hero, gets drafted for peak nostalgia.

  "Tommy Heinsohn being in love with Walter McCarty really increased our perception of him." —Will [20:08]

• Mark Blount is selected for his solid, if unspectacular, run at center.
• Search for post-Antoine answers leads to rookie Al Jefferson’s arrival and the fleeting Ricky Davis period.

  "Al Jefferson is probably one of those guys that is going to be looked at as one of the best pure post scorers of this time." —Greg [29:42]

• Delonte West’s emergence and underappreciated contributions highlight the search for silver linings in bad years.

  "Delonte West was one of those role players who just helped you win." —Will [36:19]

4. The Dark Ages & The KG Trade Setup

[37:03–41:52]

• Revisiting the 18-game losing streak and tanking era. Tony Allen gets his due for his pre-injury scoring outburst and defensive tenacity.

  "Tony Allen was really showing some stuff...he actually made comments insinuating he'd be part of the big four." —Will [38:44]

5. The Big Three Era: Rebirth and Glory

[41:52–50:03]

• 2007–08: No drama—Kevin Garnett is the obvious pick when first eligible.

  "This is probably, along with you taking Paul Pierce as the first pick, one of the two easiest picks of the entire draft." —Will [42:46]

• 2008–09: Greg drafts Ray Allen, specifically for his elevated play during the KG-injured season and legendary playoff duels.
• Rondo's ascension snagged next.
• Big Baby Davis and the Doc Rivers “Ubuntu” years get their shout-outs, too.

  "He was on something—he could shoot that thing, right?" —Will (on Wally Szczerbiak) [32:37]

6. Post-Big Three & the Stevens Years

[51:52–66:23]

• Avery Bradley picked for his defense and impact on team culture.

  "They [KG & Pierce] love Avery Bradley. Absolutely love Avery Bradley." —Will [52:41]

• Brandon Bass, Jared Sullinger, and Evan Turner represent the “bridge years” of grit and overachieving rosters.
• Greg: “I feel like my frontcourt is looking pretty good, pretty stacked... as we saw, Brandon Bass can guard the three, especially when it's LeBron.” [54:46]
• Isaiah Thomas’s arrival as a folk hero, snatched up by Greg.

  "Peak IT, right? We only get him for half a season, we don't know how good he is..." —Greg [59:09]

7. Brad Stevens’ Masterclass & Early Playoff Surprises

[60:33–66:23]

• The hosts marvel at Brad coaching a .500 roster to a five seed (Evan Turner, Jae Crowder, Amir Johnson, etc.).

  "That team is a five seed... that's a Brad Stevens masterpiece." —Will [61:17]

• Marcus Smart (Year 3) and Jaylen Brown (Year 3) mark turning points in Celtics player development and foreshadow the next stars.

  "I think this is when people really started to get excited about what Marcus Smart was for this Celtics team." —Greg [62:46]

8. Tatum, Brown, & The Modern Contenders

[66:23–78:27]

• Al Horford and Jalen Brown become signature picks for their respective teams.

  "That's your—Al's my guy, Jalen's your guy. It all makes sense." —Will [66:23]

• The bubble season: Jason Tatum (Year 3) is an easy choice for Will; his All-NBA turn and the Raptors-Heat playoff gauntlet are relived.
• Kemba Walker selected, but with regret over his injuries.
• Derrick White chosen as the emerging glue guy in the Finals run.
• Final picks round out with Rob Williams, Malcolm Brogdon agonized over, and Porzingis (from the 2023–24 title team) rounding out Will's team.

  "I'm just going with a really big team here... My team is loaded." —Will [76:02]

9. Final Rosters & Debate

[76:26–77:49]

• Greg's "Quarter Century Celtics":
  • Starters: Isaiah Thomas, Ray Allen, Paul Pierce, Jalen Brown, Al Jefferson
  • Bench: Marcus Smart, Tony Allen, Walter McCarty, Big Baby Davis, Brandon Bass, Kemba Walker, Rob Williams
• Will's "Quarter Century Celtics":
  • Starters: Rajon Rondo, (Jason Tatum), Antoine Walker, Kevin Garnett, Al Horford
  • Bench: Avery Bradley, Delonte West, Evan Turner, Jared Sullinger, Mark Blount, Derrick White, Kristaps Porzingis

"We have to include Jrue as the 'auto-QB,' the honorary captain for this era... this last championship doesn't happen without Jrue Holiday." —Greg [77:35]

Notable Quotes & Memorable Moments

• On picking for the actual Celtics years, not careers:

  "If you're drafting Shaq, you're not getting Shaq's whole career. You're getting what he was for the Celtics." —Will [08:04]

• On the legendary cult of Walter McCarty:

  "The amplification of his career locally is astounding… When you look back on it." —Will [22:25]

• On the hopeless 2007 tanking squad:

  "3 and 39 without Paul Pierce—that’s... I thought I hit the over!" —Will [37:49]

• On Big Al Jefferson’s legacy:

  “Big Al… one of the best pure post scorers of this time… never made an All-Star team, but made an All-NBA team.” —Will [29:55]

• On drafting favorites vs. pure value:

  "I might be giving you a gift here, but I'm going to do it… I really liked Evan Turner." —Will [61:17]

• Draft Postscript:

  "We're going to put this up for people to look at on socials...Who did we not draft? Let us know." —Will [77:49]

Recurring Podcast Banter

• Greg’s ongoing stomach bug, suspected to be chicken parm poisoning, becomes a running gag in the opening.
• The duo’s age is a frequent, self-deprecating trope.
• Multiple callbacks to nostalgia: Tommy Heinsohn’s “I love Walter!”; memorable playoff heartbreaks and local radio tropes.
• Impressions of the “deep cut” Celtics roster names.

Summary

This episode is a treasure trove for Celtics diehards and NBA nostalgia heads. It blends an inventive fantasy draft format with spirited debates on “what ifs”, heartbreak, and the moments that defined the late-Auerbach, Paul Pierce, Big Three, and Jay-Ten eras in Boston. Will and Greg’s banter and encyclopedic knowledge make the journey personal and entertaining, putting a human face on two and a half decades of green history. The final rosters each tell a story not just of franchise stars, but of a fan’s emotional connection—and sometimes pain—in following the Celtics through rebuilding, resurgence, despair, and ultimate triumph.

Listen or Follow Up

• Vote on which roster wins, share your own “25 years, 25 Celtics” teams, or revisit old playoff series!
• Follow the show on social media: @GreenEnvyPod
• Look out for graphics of the drafted teams and bonus listener reactions.

Summary prepared in the irreverent, passionate, and slightly obsessive tone of lifelong Celtics fans, true to the hosts’ style.