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The Trade-Off: Celtics Shed Jrue Holiday, Secure Cap Freedom with Simons Bet
Boston got younger, cheaper, and more flexible. Portland got tougher, older—and possibly stuck. This isn’t just a trade. It’s a pivot point.
Samuel Rogers
June 28, 2025
📝 The Deal
🔁 Celtics receive:
Anfernee Simons, 26-year-old SG (expiring $27.6M deal)
Two future 2nd-round picks
🔁 Trail Blazers receive:
Jrue Holiday, 35-year-old G (3 years, $104.4M remaining incl. player option)
💸 Capology: Boston’s Financial Masterstroke
Metric | Before Trade | After Trade |
|---|---|---|
Tax Penalty | $39.4M | $0 (under second apron) |
Jrue’s Cap Hit | $37.1M (2025–26) | $0 |
Simons’ Hit | $27.6M (expiring) | $27.6M |
Net Cap Flex | — | +$18M below 2nd apron |
Takeaway: Boston just gained optionality. Massive cap room plus picks is a rare double win. Think of it as buying themselves a championship Plan B.
📊 Player Performance Deep Dive
🎯 Anfernee Simons (Age 26)
2024–25 Stats:
19.3 PPG | 4.8 APG | 3.3 RPG
36.3% 3PT on 8.5 attempts/game
52.1% eFG | 114 ORtg | 23.7% USG
Strengths: Spacing gravity, pull-up shooting, secondary creation
Weaknesses: Defensive liability (Def Raptor: -2.6), struggles in pick-and-roll defense
🛡️ Jrue Holiday (Age 35)
2024–25 Stats:
11.1 PPG | 4.4 APG | 5.2 RPG
56.5% TS | 103 ORtg | 18.1 P/100
1st in Defensive EPM among guards
Strengths: Perimeter defense, championship pedigree
Weaknesses: Rapid offensive decline, expensive aging curve
🧠 Advanced Analytics: Efficiency, Usage, Defense
Metric | Simons | Holiday |
|---|---|---|
P/100 Poss | 27.4 | 18.1 |
Offensive EPM | +1.6 | -0.2 |
Defensive EPM | -2.1 | +2.9 |
3PT Shot Quality | 1.14 PPP | 0.88 PPP |
Contract AAV | $27.6M (1yr) | $34.8M (avg. over 3yrs) |
Efficiency delta: Simons adds spacing, but at a cost—he’ll need to be hidden on D. Boston’s scheme can absorb it. Holiday’s elite D is irreplaceable—but aging offense made it unsustainable.
🧩 Strategic Lens
🟢 Boston Celtics: Grade A–
Smart asset swap with asymmetric upside
26-year-old Simons fits Jayson Tatum’s timeline
Added 2 picks = future maneuverability
Luxury tax reset preempts new CBA roster constraints
Reality check: Tatum’s injury opened a quiet rebuild lane. Boston just sprinted through it.
🔴 Portland Trail Blazers: Grade C
Betting big on leadership over scoring
Jrue may limit young core’s touches: Scoot Henderson, Camara, Clingan
If they don’t win now, they’re locked in aging asset with declining output
Reality check: This smells like a franchise hedging against rebuilding fatigue.
🔮 What Happens Next?
📈 Simons' Impact Scenarios
Breakout scorer in Boston: He commands a new deal or becomes high-leverage trade bait
Defensive liability outweighs offense: Flip at deadline or let walk with cap relief
Net gain: Value floor is high thanks to picks
📉 Holiday's Fit in Portland
Mentor role + elite D: Elevates defense, stabilizes Scoot
Offensive fade continues: Hurts spacing, saps pace
Worst-case: Stuck with $37M player option on an aging PG in 2027