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Replay Information

Please note that the investor broadcast associated with the following slides is available. The presentation can be accessed by following the link below:

https://roadshow.munios.com/roadshow-viewer.aspx?e=3USA1

The full slide deck for this call is found in the pages below. These slides as well as those of prior investor calls may also be accessed by visiting the Investor and Rating Agency Presentation Archive on the Commonwealth’s investor website at: www.massbondholder.com

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The Commonwealth of Massachusetts

Commonwealth Transportation Fund Revenue Bonds Federal Highway Grant Anticipation Notes INVESTOR PRESENTATION

$200,000,000* Commonwealth Transportation Fund Revenue Bonds (Rail Enhancement & Accelerated Bridge Programs), 2019 Series A $53,500,000* Federal Highway Grant Anticipation Notes (Accelerated Bridge Program), 2019 Series A

* Preliminary, subject to change

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Disclaimer

This presentation has been prepared by the Commonwealth of Massachusetts, as of November 4, 2019, to provide summary information relative to the proposed offering of the Commonwealth of Massachusetts, $200,000,000* Commonwealth Transportation Fund Revenue Bonds 2019 Series A and $53,500,000* Federal Highway Grant Anticipation Notes 2019 Series A. The information contained in this investor presentation speaks only as of the date such information was prepared and has not been updated since that date. Accordingly, such information may not address all factors which may be material to an investor and may contain omissions of fact or statements that are not accurate because of the passage of time or changes in facts or circumstances subsequent to the date of such information. The Commonwealth is under no obligation to update any of the information set forth in this investor presentation. The presentation is incomplete and investment decisions relating to the Commonwealth Transportation Fund Revenue Bonds and the Federal Highway Grant Anticipation Notes should be based only upon the Official Statements of the Commonwealth relating to such securities. The provision

  • f access to this presentation does not constitute an offer to sell or the solicitation of an offer to buy any securities described or mentioned in the
  • presentation. The information contained herein does not constitute a sufficient basis for making a decision with respect to the purchase or sale of any

security and is not intended to constitute investment advice of any kind. Commonwealth securities are sold only by means of an Official Statement and through registered broker-dealers. The information set forth herein includes information obtained from non-Commonwealth sources that are believed to be reliable, but such information is not guaranteed as to accuracy or completeness and is not to be construed as a representation by the Commonwealth as Issuer of the securities, Citigroup Global Markets Inc. and J.P. Morgan Securities LLC as Representatives of the Underwriters, or PFM Financial Advisors LLC as Financial

  • Advisor. All information and expressions of opinion herein are subject to change without notice. The Commonwealth undertakes no obligation to

provide any additional information or to update any of the information or the conclusions contained herein. This presentation contains certain forward-looking statements that are subject to a variety of risks and uncertainties that could cause actual results to differ from the projected results, including without limitation general economic and business conditions, conditions in the financial markets, the financial condition of the Commonwealth and various state agencies and authorities, receipt of federal subsidies, litigation, arbitration, force majeure events and various other factors that are beyond the control of the Commonwealth and its various agencies and authorities. Because of the inability to predict all factors that may affect future decisions, actions, events or financial circumstances, what actually happens may be different from what is set forth in such forward-looking statements. Forward-looking statements are indicated by use of such words as “may,” “will,” “should,” “intends,” “expects,” “believes,” “anticipates,” “estimates” and others. By viewing this investor presentation, you acknowledge that you understand and agree to the provisions of this page. *Preliminary, subject to change

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Commonwealth Transportation Fund Revenue Bonds  Series: 2019 Series A  Principal Amount: $200,000,000*  Interest Payment Dates: June 1 and December 1, beginning June 1, 2020  Final Maturity Date: Due June 1, 2049  Security: Commonwealth Transportation Fund. Primary revenue sources: Motor Fuels Tax and Registry Fees  Use of Proceeds: Fund costs of certain significant rail improvement projects outside the MBTA’s regular capital program (Rail Enhancement Program) and may also be used to fund additional capital project costs under the Accelerated Bridge Program  Current Ratings on Parity Debt: Aa1/AA+/AAA (Moody’s/S&P/Kroll)  Optional Redemption: TBD

Transaction Summary – CTF Bonds

* Preliminary, subject to change

2019 Series A – Preliminary Amortization by Maturity Year 2049 Term Bond $200,000,000

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Transaction Summary - GANs

Federal Highway Grant Anticipation Notes, 2019 Series A  Principal Amount: $53,500,000*  Interest Payment Dates: June 15 and December 15, beginning June 15, 2020  Final Maturity Date: Due June 15, 2027  Security: Federal Highway Reimbursements and net amount credited to the Commonwealth Transportation Fund  Use of Proceeds: Proceeds from the 2019A Notes will be used to fund additional capital project costs of the Accelerated Bridge Program  Current Ratings on Parity Debt: Aa2/ AAA (Moody’s/S&P)  Optional Redemption: Each maturity will be subject to redemption on any date on and after the June 15 immediately preceding the applicable maturity date at the option of the Commonwealth and as determined at pricing

2019 Series A – Preliminary Amortization by Maturity Year Due (06/15) Amount

2026 $23,500,000 2027 30,000,000

* Preliminary, subject to change

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Key Credit Strengths: Commonwealth Transportation Fund

Key CTF Credit Points

Diverse and Stable State-wide Revenue Stream

  • Pledged revenues include fuel and non-fuel sources with Motor Fuels Tax and Registry Fees
  • Revenue collections are strong with diversity in timing
  • Low degree of correlation among pledged revenue streams limits volatility

Strong and Diverse Economic Base

  • Statewide taxes and fees, on large and diverse regional economy
  • Broad and diverse economy that encompasses over 6.9 million residents
  • Per capita personal income levels in excess of 130% of the national average in 2018
  • Presence of multiple major universities and both stable and growing industries

Debt Service Coverage and Liquidity

  • Strong debt service coverage of approximately 7.1x* based on actual preliminary FY2019 CTF revenues of $1.4 billion
  • Pro forma debt service coverage, including expected future issuances, estimated at 5.1x*
  • Conservative 4x ABT further supports liquidity and a healthy overall leverage position
  • Strong debt service set asides (1/10th principal and 1/5th interest)

Legal Protections Revenue Pledge

  • NO Pledged Funds may be applied to “any other use” until appropriation has been made sufficient to pay principal

and interest

  • Massachusetts Constitution requires all revenue from vehicle, fuel and motor vehicle license and registration fees be used

for transportation purposes only

  • Trust Agreement does not allow the Commonwealth to change the rate of the Registry Fees or the Motor Fuels Tax unless

Net Pledged Revenues exceed 4.0x MADS coverage after the changes

* Preliminary, subject to change

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Key Credit Strengths: Federal Highway Grant Anticipation Notes

Key GANs Credit Points

“Double Barrel” Pledge

  • The Commonwealth has enjoyed a long history of stable funding from the Federal-Aid Highway Program
  • Use of Federal Highway Reimbursements to pay GANs Debt Service does not require a state appropriation
  • Annual federal highway reimbursements assumed to be $669 million for FY2020-2027 based on FHWA guidance of

annual base Obligation Authority of $669 million for FFY 2020-2024

  • In addition, net CTF Pledged Funds are available for annual debt service. These net revenues have averaged $1.1

billion annually for the past 5 years Debt Service Coverage* and Liquidity

  • Strong debt service coverage of 12.8x to 21.4x, incorporating Federal Highway Reimbursements and Net CTF pledged

funds through FY2027

  • Advance annual set aside for payment of principal and semi-annual interest

Additional Bonds Test

  • Two Pronged Test from a Dual Revenue Pledge – Two Independent Sources Provide Combined 4.0x ABT

1. Amount of Federal Highway Reimbursements during any 12 consecutive months out of an 18-month period (with the last full month proceeding the date of issuance of the Additional Notes) must not be less than 1.5x MADS in the current or any future FY; and 2. Amount of Net CTF Pledged Funds received during same 12 consecutive months must not be less than 2.5x MADS in the current or any future fiscal year Legal Protections CTF Revenue Pledge

  • NO Pledged Funds may be applied to “any other use” until appropriation has been made sufficient to pay principal

and interest

  • Massachusetts Constitution requires all revenue from vehicle, fuel and motor vehicle license and registration fees be used

for transportation purposes only

  • Trust Agreement does not allow the Commonwealth to change the rate of the Registry Fees or the Motor Fuels Tax unless

Net Pledged Revenues exceed 4.0x MADS coverage after the changes

* Preliminary, subject to change

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Introduction to the GANs and CTF Credits

 Federal Highway Grant Anticipation Notes (GANs)

  • Authorized to be issued for the Accelerated Bridge Program
  • GANs final maturity no later than June 30, 2027

Program Authorized Spending Prior Financed Spending 2019 Financed Spending (a) Authorization Remaining(b) CTF $1,876 M $1,846 M $15 M $15 M GANs 1,108 M 1,028 M 65 M 15 M Total ABP 2,984 M 2,874 M 80 M 30 M

Accelerated Bridge Program

Authorized Spending Prior Financed Spending 2019 Financed Spending (a) Authorization Remaining (b) CTF Revenue Bonds GO Bonds CTF Revenue Bonds $6,684 M $1,324 M $49 M $233 M $5,078 M

Rail Enhancement Program

 Commonwealth Transportation Fund (CTF) Revenue Bonds

  • Authorized to be issued under two programs:
  • Accelerated Bridge Program (ABP)
  • Rail Enhancement Program (REP)
  • CTF Revenue Bonds final maturity no later than
  • June 30, 2046 for ABP
  • June 30, 2049 for REP

(a) Preliminary, subject to change (b) Under the Accelerated Bridge Program Act, the Commonwealth may issue any portion of the GANs authorized therein as special obligation bonds and may issue any portion of the special obligation bonds authorized therein as GANs, provided that the aggregate amount (including net premium) of such special

  • bligation bonds and GANs shall not exceed $2.984 billion.

(a) Preliminary, subject to change (b) Chapter 79 authorized the issuance of approximately $6.7 billion of bonds of the Commonwealth either as general obligation bonds or special obligation bonds issued under the Special Obligation Act.

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Rail Enhancement Program (REP)

Rail Enhancement Program

  • Authorized by Chapter 79 of the Acts of 2014 to provide for the issuance of either general obligation or special
  • bligation bonds to fund capital expenditures of MassDOT for the benefit of the MBTA and for other rail improvements in

the Commonwealth

  • Intended to provide financing for certain significant rail improvement projects in the Commonwealth outside the MBTA’s

regular capital program

  • Proceeds from the 2019 Bonds are expected to finance certain significant rail improvement projects in the Commonwealth
  • utside the MBTA’s regular capital program some of which are highlighted below. The Appendix provides more details on

each of these projects.

  • Green Line Extension: This project will extend the existing MBTA Green Line by utilizing two distinct branches

within the existing railroad right-of-way: a “mainline” branch which will operate along the existing Lowell commuter rail line, beginning at a relocated Lechmere Station in Cambridge and traveling through Somerville to College Avenue in Medford, with a branch line operating within the right-of-way for the existing Fitchburg commuter rail line leading to Union Square in Somerville

  • Red Line and Orange Line Improvements Program: This program involves procurement and replacement of new

Red Line and Orange Line vehicles to improve reliability, accessibility and energy efficiency and associated improvements to facilities, track and signal infrastructure to address the state of good repair needs of the MBTA’s Red and Orange Lines. New cars will feature increased capacity and additional seating, wider and electrically

  • perated doors, accessible areas in each car, LED lighting, updated HVAC systems and improved communication

systems.

  • South Coast Rail Program: This project will offer a reliable transit connection between southeastern

Massachusetts and Boston. Riders will be able to take a 1-seat trip – no transfers needed – from Fall River and New Bedford into Boston. Taunton, New Bedford, and Fall River are the only major cities within 50 miles of Boston that do not currently have commuter rail access to Boston.

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Accelerated Bridge Program

  • In 2008, the Commonwealth had 543 structurally deficient bridges, and projections of this number climbing to almost 700 by 2016.

The Accelerated Bridge Program Act was passed with a goal of reducing the state’s backlog of structurally deficient bridges below 450 by September 30, 2016.

  • The Accelerated Bridge Program Act authorized the issuance of up to $1.876 billion in special obligation bonds of the Commonwealth

secured by revenues in the Commonwealth Transportation Fund and the issuance of up to $1.108 billion of Federal Highway Grant Anticipation Notes (“GANs”) secured by reimbursement received or to be received by the Commonwealth from federal highway funds to the accelerated capital improvement of bridges and related infrastructure

  • The goal of the program was exceeded with the number of structurally deficient bridges reduced to 432 as of

September 30, 2016, a decline of 20%.

  • As of September 1, 2018, the ABP has completed 191 bridge projects, with seven remaining bridge projects in
  • construction. Over the course of the program, well over 283 bridges have been rehabilitated or replaced, with

many more improved for safety and preserved for extended lifecycle.

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Commonwealth Transportation Fund Revenue and Credit Considerations

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CTF has Strong Credit and Legal Features

Strong legal protections and underlying fundamentals have been the hallmarks of CTF's credit profile since its inception in 2010.  Strong Legal Protections Safeguard Revenue Pledge

  • Massachusetts Constitution requires Pledged Funds to be expended for transportation purposes only
  • State Statutes provide for covenants in the Trust Agreement to ensure that Pledged Funds are deposited in the CTF

and applied to debt service before they can be used for any other purpose  Strong and Diverse Economic Base

  • Broad and diverse economy that encompasses over 6.9 million residents
  • Per capita personal income levels in excess of 130% of the national average in 2018
  • Massachusetts is home to multiple major universities and both stable and growing industries

 Diverse and Stable State-wide Revenue Stream

  • Diverse mix of six motor fuels taxes and registry fees as well as federal BABs subsidies generates over $1.402 billion
  • f pledged revenue annually
  • Low degree of correlation among pledged revenue streams limits volatility
  • Revenue collections are strong with diversity in timing

 Superior Coverage and Liquidity

  • Pro forma debt service coverage, including expected future issuances, estimated at 5.1x
  • Conservative 4x ABT further supports liquidity and a healthy overall leverage position
  • Strong debt service set asides (1/10th principal and 1/5th interest)

 Transportation Capital Investment Drives Economic Development

  • CTF transportation projects support economic development across the Commonwealth
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Pledged Funds are Diverse and Stable

__________ Preliminary revenues for Fiscal Year 2019 revenues are preliminary, unaudited and subject to change. (1) Chapter 64A: 99.85% of the 24 cents/gallon tax flows to CTF Pledged Funds. 6.86 cents/gallon is pledged on a senior basis to Existing Gas Tax Bonds. Amount shown is prior to debt service for the Existing Gas Tax Bonds. (2) Chapter 64E: Special Fuels Tax levied on each of special fuels (24 cents) and liquefied gas sold or used in the Commonwealth. 100% of the 24-cent tax is included as CTF Pledged Funds. (3) Chapter 64F: Motor Carrier Tax levied on each gallon of gasoline and special fuels acquired outside and used within the Commonwealth. (4) Registry fees received by Registry of Motor Vehicles pursuant to Section 33 of Chapter 90 of the General Laws. (5) Direct payments received from US Treasury related to BABs/RZEDBs.

Total Preliminary FY2019 CTF Pledged Funds: $1.402 Billion

Ch 64A Gas Tax(1) BABs/RZEDBs Subsidies Ch 64E Special Fuels Tax(2) Ch 64F Motor Carrier Tax(3) License Registration Registry Information

Motor Fuels Taxes Registry Fees(4)

Direct Payments(5)

 Pledged Revenues include fuel and non-fuel sources with Motor Fuels Taxes (55.2%) and Registry Fees (44.0%)  State-wide taxes and fees, on a large and diverse regional economy  Revenue collections are strong with diversity in timing:

 Motor Fuel Taxes are collected monthly by the Department of Revenue  Registry Fees are collected daily at Registry branch and other locations  Direct Payments are deposited on a semi-annual basis

$672.9 Million (48.0%) $11.6 Million (0.8%) $616.8 Million (44.0%) $100.9 Million (7.2%)

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Pledged Funds – Historically Consistent and Reliable

 Pledged Funds have consistently totaled over $1.1 billion annually  Historical performance demonstrates the strength, consistency and reliability of revenues  Diversity of CTF Pledged Funds mitigates the effect of potential declines in gasoline consumption  Pledged Funds have increased as CTF program initiatives have expanded

Historic Commonwealth Transportation Fund Pledged Funds ($ in thousands)

Fiscal Year Ending June 30 Gas Tax, Special Fuels Tax, And Motor Carrier Tax Registry Fees Total % Growth/ Decline

2019(1) $773,789 $616,830 $1,390,619 0.75% 2018 767,520 612,780 1,380,300 1.01% 2017 767,855 598,683 1,366,538 1.56% 2016 764,848 580,426 1,345,274 0.71% 2015(2) 754,392 581,686(3) 1,336,078 5.72% 2014 730,640(2) 533,194 1,263,834 7.84% 2013(3) 649,779 522,199 1,171,978 0.27% 2012 660,176 508,608 1,168,784 1.17% 2011 659,183 496,034 1,155,217 1.44% 2010(4) 653,045 485,789(4) 1,138,834 7.88%

Source: Fiscal Years 2010-2018, Office of the Comptroller of the Commonwealth, audited, and fiscal year 2019, Department of Revenue (“Pledged Motor Fuels Tax”) and MassDOT (“Registry Fees”), unaudited (1) Fiscal Year 2019 revenues are preliminary. (2) 2015 increase in revenues due to increases in certain Registry Fees. (3) Effective July 31, 2013, motor fuel tax increased to 24 cents/gallon from 21 cents/gallon. (4) 2010 increase in revenues due to change in fee structure.

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Gasoline Consumption is Relatively Inelastic and Tax Rates Compare Favorably to Neighboring States Historical Gasoline Sales Comparison of Gasoline Tax Rates for Selected Northeastern States

(in cents per gallon as of October 1, 2019 for selected NE states)

Even with the significant volatility in underlying gasoline prices, gasoline consumption has remained relatively stable over the last 10 years.

Average Price

  • f Gasoline(1)

Gasoline Consumed (millions of gallons)(2) 2019(3) $2.750 2,808 2018 2.708 2,787 2017 2.347 2,796 2016 2.282 2,781 2015 2.925 2,739 2014 3.613 2,733 2013 3.684 2,721 2012 3.652 2,772 2011 3.204 2,766 2010 2.694 2,750

Source(s): “Average Price of Gasoline”: U.S. Department of Energy, Energy Information Administration; “Non-Farm Employment”: U.S. Bureau of Labor Statistics; “Gasoline Consumed”: Department of Revenue.; American Petroleum Institute. Totals may not add due to rounding. (1) Reflects the Average Price of Gasoline ($/gallon) in all of Massachusetts. (2) Based on Historical Gasoline Tax Collections pursuant to Chapter 64A, except Aviation Fuel. See Commonwealth Motor Fuels Tax – Refunds and Abatements from Gasoline Tax. (3) Fiscal year 2019 figures are preliminary and subject to change.

Excise Tax Other Taxes and Fees Total

New York 8.05¢ 37.36¢ 45.41¢ Connecticut 25.00 14.31 39.31 Rhode Island 34.00 1.00 35.00 Vermont 12.10 18.84 30.94 Maine 30.00 0.01 30.01 Massachusetts 24.00 2.54 26.54 New Hampshire 22.20 1.63 23.83

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Flow of Pledged Funds Under the Trust Agreement

State Treasury (Sweep Account) Commonwealth Transportation Fund Revenue Account(2) To Commonwealth Transportation Fund, Free and Clear of Lien of Trust Agreement(4)

To GAN Trustee

(1) It is not unusual for the budget process to extend slightly into the next fiscal year, with the final enactment of the budget occurring in early or mid-July. Interim budgets are typically enacted to provide funding after the end of the fiscal year until the full budget can be enacted and approved by the Governor. (2) Includes Non-Motor Fuels Subaccount and Motor Fuels Subaccount. (3) Debt service for the 1994 Trust Agreement Bonds is subject to appropriation as part of the Commonwealth's annual budgeting process as outlined in the respective Official Statement. (4) Following deposit into the Debt Service Fund, funds flow into the Subordinated Debt Service Fund (not currently active).

Trustee Held Fund

  • Commonwealth Held Fund

Ch 64E Special Fuels Tax

1994 Trust Agreement for Debt Service on 1994 Trust Agreement Bonds(3)

Debt Service Fund

Trustee Held Fund, Subject to appropriation

  • [Transfer to Revenue Account not subject to annual appropriation]

[Transfer to Debt Service Fund is subject to annual appropriation]

Ch 64A Gas Tax License Ch 64F Motor Carrier Tax Registration Registry Information

Direct Payments

 CTF Pledged Funds are constitutionally dedicated for transportation, and as provided in the Special Obligation Act, must be used to pay debt service before the State can access the funds for any other transportation related purpose  The Massachusetts Constitution requires nearly all spending, including the CTF, to be subject to appropriation  State depository accounts are swept daily by the Treasury, credited to the appropriate accounts  DOR and MassDOT deliver a certificate to the Trustee stating the amount of Pledged Funds collected each month within 8 business days of month end  The Treasurer deposits Pledged Funds into the Revenue Account held by the Trustee within 2 business days of receiving the certificate, which deposit is not subject to annual appropriation  Debt service is appropriated annually as part of the Commonwealth’s annual budgeting process. Until an appropriation has been made, no funds may be transferred out of the Revenue Account for any purpose(1)

Pledged Funds

[MassDOT and DOR deliver certificate to Trustee]

[ ------- Collected Monthly by DOR ------- ] [ -- Collected Daily by Registry of Motor Vehicles -- ]

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 The Commonwealth plans to issue approximately $1.49 billion* in aggregate CTF bond par, raising $1.85 billion* in net bond proceeds (including original issue premium), with projected spending through FY2024, inclusive of the 2019 Series A Bonds  Actual amount and timing of future bond issues are subject to change  Based on currently projected issuance, and assuming no growth in pledged revenues, MADS coverage for the CTF Bonds following the issuances shown above is projected to be 5.1x

CTF Projected Issuance*

Fiscal Year Par Proceeds 2021(1) $200.0 million $249.0 million 2021 $350.0 million $435.6 million 2022 $325.0 million $402.2 million 2023 $325.0 million $404.2 million 2024 $291.3 million $362.4 million Total $1,491.3 million $1,853.4 million

(1) 2019 Series A Offering

* Preliminary, subject to change

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Pro Forma CTF Coverage for 2019 Series A and Future Offerings*

  • Assuming no revenue growth, total projected debt service coverage on the 2019 Series A CTF Bonds is approximately 7.1x* through FY2049.

* Preliminary, subject to change (1) Estimated debt service coverage for fiscal year 2020 and thereafter is based on the Commonwealth’s projected revenues for fiscal year 2019, which are preliminary, unaudited and subject to change, and assuming no growth in such receipts in future years. Debt service projections for Bonds to be issued in fiscal years 2020 through 2024 are estimates based on current program needs and are subject to change. (2) Consists of (i) 17.104¢ per gallon of Chapter 64A Gasoline Tax, (ii) 100% of the Special Fuels Tax and Motor Carrier Tax, (iii) Registry Fees expected to be credited to the Commonwealth Transportation Fund, (iv) Projected Excess from Prior Pledged and (v) Direct Payments relating to the 2010 Bonds, which are assumed to be reduced by the current 5.9% reduction as a result of sequestration. (3) Reflects gross debt service on Prior CTF Bonds. (4) Assumes aggregate issuance in fiscal years 2020 through 2024 (not including the 2019 Bonds) of $1.29 billion in aggregate bond par amount, raising $1.6 billion in net bond proceeds. The final maturity for all issues is limited to 2049 pursuant to current law. Projected Debt Service on future issuance assumes current market rates. Figures are preliminary and subject to change.

CTF Bond Debt Service Coverage Projection ($ in thousands)

  • Projected debt service coverage including anticipated ABP and REP issuance through FY 2024 is estimated to be approximately 5.1x* based on aggregate

current CTF projected offerings for the programs

SFY Ending June 30 Prior CTF Bonds and 2019 Bonds Debt Service Excess Pledged Funds 2020 29,822 1,372,385 179,083 5,444 184,527 7.4x 1,187,858

  • 184,527

7.4x 1,187,858 2021 29,821 1,372,386 179,083 10,000 189,083 7.3x 1,183,303 10,208 199,291 6.9x 1,173,095 2022 29,821 1,372,386 179,084 10,000 189,084 7.3x 1,183,302 40,064 229,148 6.0x 1,143,237 2023

  • 1,402,207

183,005 10,000 193,005 7.3x 1,209,201 62,950 255,955 5.5x 1,146,252 2024

  • 1,402,207

183,003 10,000 193,003 7.3x 1,209,204 82,893 275,896 5.1x 1,126,311 2025

  • 1,401,852

182,956 10,000 192,956 7.3x 1,208,895 82,868 275,824 5.1x 1,126,027 2026

  • 1,401,468

182,909 10,000 192,909 7.3x 1,208,559 82,844 275,753 5.1x 1,125,715 2027

  • 1,401,031

182,848 10,000 192,848 7.3x 1,208,183 82,818 275,666 5.1x 1,125,365 2028

  • 1,400,570

182,787 10,000 192,787 7.3x 1,207,783 82,788 275,575 5.1x 1,124,996 2029

  • 1,400,083

182,727 10,000 192,727 7.3x 1,207,356 82,750 275,477 5.1x 1,124,606 2030

  • 1,399,570

182,659 10,000 192,659 7.3x 1,206,910 82,718 275,377 5.1x 1,124,192 2031

  • 1,399,027

182,590 10,000 192,590 7.3x 1,206,437 82,678 275,269 5.1x 1,123,759 2032

  • 1,398,444

182,514 10,000 192,514 7.3x 1,205,930 82,643 275,157 5.1x 1,123,287 2033

  • 1,397,828

182,433 10,000 192,433 7.3x 1,205,395 82,604 275,037 5.1x 1,122,791 2034

  • 1,397,177

182,348 10,000 192,348 7.3x 1,204,830 82,557 274,905 5.1x 1,122,272 2035

  • 1,396,490

182,260 10,000 192,260 7.3x 1,204,230 82,510 274,770 5.1x 1,121,720 2036

  • 1,395,763

182,162 10,000 192,162 7.3x 1,203,600 82,464 274,626 5.1x 1,121,136 2037

  • 1,394,995

182,063 10,000 192,063 7.3x 1,202,932 82,415 274,477 5.1x 1,120,517 2038

  • 1,394,118

181,949 10,000 191,949 7.3x 1,202,169 82,358 274,307 5.1x 1,119,811 2039

  • 1,393,015

181,804 10,000 191,804 7.3x 1,201,211 82,285 274,089 5.1x 1,118,926 2040

  • 1,391,850

181,653 10,000 191,653 7.3x 1,200,197 82,207 273,860 5.1x 1,117,990 2041

  • 1,390,619

181,489 10,000 191,489 7.3x 1,199,130 82,129 273,619 5.1x 1,117,000 2042

  • 1,390,619

181,490 10,000 191,490 7.3x 1,199,129 82,127 273,618 5.1x 1,117,001 2043

  • 1,390,619

181,493 10,000 191,493 7.3x 1,199,126 82,122 273,615 5.1x 1,117,004 2044

  • 1,390,619

181,493 15,000 196,493 7.1x 1,194,126 77,122 273,616 5.1x 1,117,003 2045

  • 1,390,619

181,489 14,750 196,239 7.1x 1,194,380 77,378 273,617 5.1x 1,117,002 2046

  • 1,390,619

181,492 14,500 195,992 7.1x 1,194,627 77,626 273,618 5.1x 1,117,001 2047

  • 1,390,619

64,750 47,395 112,145 12.4x 1,278,474 161,472 273,617 5.1x 1,117,003 2048

  • 1,390,619

64,745 47,398 112,143 12.4x 1,278,476 161,472 273,615 5.1x 1,117,004 2049

  • 1,390,619
  • 112,140

112,140 12.4x 1,278,479 161,474 273,614 5.1x 1,117,005 1994 Trust Agreement Bonds Total Debt Service Projected CTF Pledged Funds2 Excess Pledged Funds Total Debt Service Coverage1 Prior CTF Bonds Debt Service3 Debt Service on 2019 Bonds Prior CTF Bonds & 2019 Bonds Debt Service Coverage1 Total Debt Service on Future Bonds4 Total CTF Bonds Debt Service4

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Federal Highway Grant Anticipation Notes Revenue and Credit Considerations

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GANs Double Barrel Pledge / Credit Features Protect Investors

Double-Barrel Pledge and Multiple Other Credit Features Create High Quality Transportation Credit

Two Independent Revenue Streams with Extremely Low Joint Default Probability Underpin GANs Credit

  • Federal Highway Reimbursements pay GANs debt service – no state appropriation required
  • Long history of stable funding from FHWA: averaging over $600mm annually
  • Net CTF Pledged Funds are available to pay debt service averaging $1.1 billion annually
  • Diverse mix of 6 motor fuels taxes/registry fees: over $1.4 billion annually

Strong Pro-Forma Debt Service Coverage Following Issuance of 2019 Series A Bonds

  • FHWA reimbursements alone cover GANs debt service over 4.8x
  • Net CTF Pledged Funds alone cover GANs debt service over 8.0x
  • Aggregate Coverage of GANs debt service over 12.8x

Two-Pronged Additional Bonds Test Results in Combined Coverage of 4x MADs

  • FHWA reimbursements must not be less than 1.5x MADs
  • Net CTF Pledged Funds must not be less than 2.5x MADs

Advanced Annual Set-Aside for Payment of Principal and Semi-Annual Interest

  • Debt service set aside (one-year in advance) provides bondholders with a security feature that is the equivalent of a

fully funded MADs Debt Service Reserve Fund

Transportation Capital Investment Drives Economic Development

  • GANs transportation projects support economic development across the Commonwealth
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GANs Flow of Funds and Double Barrel Security

Federal Highway Reimbursements

Credit Structure for GANs

GANs

2010 Trust Agreement

CTF Pledged Funds Existing Gas Tax Bonds CTF Bonds

1994 Trust Agreement 2010 Trust Agreement

Excess Net CTF Pledged Funds of More Than $1.1 Billion Per Year Provide Independent Second Barrel Security for the GANs

6.86 cents/gallon

  • f Gas Tax Only

Excess

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Credit Strength of the FHWA Funding for GANs

  • The Commonwealth has enjoyed a long history of stable funding from the Federal-Aid Highway Program (the

“Program”)

  • The Program operates under special budget authority called contract authority that mitigates the risk of a

government shutdown

  • Through contract authority, authorized amounts are available for obligation according to the provisions of the

authorization act (in this case, the FAST Act) without further legislative action and is not at risk during the annual appropriations process

  • During the most recent government shutdown, the long-term reauthorization provided under the FAST Act allowed

disbursements for highway GARVEEs to continue uninterrupted

  • The Commonwealth believes that the Program plays a critical role in preserving the national highway system and

the chronic funding shortfalls facing transportation will ensure its continued support and reauthorization

− Since such assistance was established by the Federal-Aid Highway Act of 1956, the Program has been

reauthorized numerous times in various forms at generally increasing funding levels

− Actual payments to states have continued without interruption since 1956

  • The current authorization for the Program, as extended by the FAST Act of 2015, provides for funding through

September 30, 2020

  • Subject to becoming law, America’s Transportation Infrastructure Act of 2019 reauthorizes the highway program

under the FAST Act which expires in FY2020 for five years (2021-2025) and will be the largest amount of funding for highway reauthorization legislation in history

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Pro Forma GANs Coverage*

 Federal Highway Reimbursements and Net CTF Pledged Funds pay debt service on the Notes  Projected debt service coverage on the GANs following issuance of the 2019 Series A offering ranges from 12.8x* to 21.4x* through FY 2027

(1) Annual Federal Highway Reimbursements assumed to equal $669 million through SFY 2027. Federal Highway Reimbursements through SFY2023 also include interest subsidy payments expected to be received by the Commonwealth from the U.S. Treasury (“Direct Payments”) with respect to the 2010 Notes issued as Build America Bonds, which amounts are assumed to be subject to the current 5.9% reduction as a result of sequestration. (2) Net CTF Pledged Funds are net of amounts to be used for debt service payments on the 1994 Trust Agreement Bonds and the outstanding CTF Bonds, as well as debt service on the 2019 CTF

  • Bonds. Net CTF Pledged Funds consist of monies in the Commonwealth Transportation Fund from the following sources, subject to the prior lien of the CTF Obligations: (i) Chapter 64A Pledged Gasoline

Tax, (ii) Special Fuels Tax and Motor Carrier Tax, (iii) Registry Fees expected to be credited to the Commonwealth Transportation Fund pursuant to Section 34(iii) of Chapter 90, (iv) the portion of the Prior Pledged CTF Funds (6.86 cents per gallon of the Chapter 64A Gasoline Tax) in excess of the amounts necessary to pay debt service on the 1994 Trust Agreement Bonds and to satisfy any other requirements under the 1994 Trust Agreement, and (v) Direct Payments relating to the 2010 CTF Bonds, which are assumed to be subject to the current 5.9% reduction as a result of sequestration. See “Net CTF Pledged Funds.” (3) Represents gross debt service on the Existing Trust Agreement Notes issued in 2010, not including Direct Payments, and debt service on the other Existing Trust Agreement Notes.

Outstanding Trust Agreement Notes - Projected Debt Service Coverage after 2019 Financing

*Preliminary, subject to change SFY Ending June 30 Total Projected Pledged Revenues Existing Debt Service on Trust Agreement Notes3 Federal Highway Reimbursements Only Net CTF Pledged Funds Only 2020 669,735,982 1,187,857,861 1,857,593,843 85,342,299 1,515,833 86,858,132 7.7x 13.7x 21.4x 2021 669,542,743 1,173,095,019 1,842,637,762 109,675,671 2,675,000 112,350,671 6.0x 10.4x 16.4x 2022 669,335,951 1,143,237,461 1,812,573,412 109,676,844 2,675,000 112,351,844 6.0x 10.2x 16.1x 2023 669,114,670 1,146,251,558 1,815,366,228 109,674,970 2,675,000 112,349,970 6.0x 10.2x 16.2x 2024 669,000,000 1,126,310,817 1,795,310,817 108,800,000 2,675,000 111,475,000 6.0x 10.1x 16.1x 2025 669,000,000 1,126,027,485 1,795,027,485 108,799,500 2,675,000 111,474,500 6.0x 10.1x 16.1x 2026 669,000,000 1,125,715,385 1,794,715,385 108,800,250 26,175,000 134,975,250 5.0x 8.3x 13.3x 2027 669,000,000 1,125,364,934 1,794,364,934 108,801,000 31,500,000 140,301,000 4.8x 8.0x 12.8x Federal Highway Reimbursements1 Projected Net CTF Pledged Funds2 Debt Service on 2019 Notes Total Debt Service Total Projected Debt Service Coverage

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Conclusion and Financing Schedule

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2019 CTF and GANs Structuring and Credit Summary*

 Debt service coverage including expected future issuances of CTF Bonds is estimated to be approximately 5.1x  ABT of 4.0x  Pledged Funds for FY2019 totaled $1.4 billion and were derived from statewide taxes on a robust regional economy.  Pledged Funds are diversified and include both Motor Fuels Tax and Registry Fees  History of strong CTF Pledged Fund performance  Trust agreement covenant restricts ability to reduce Motor Fuel Taxes and Registry Fees  Constitutional provision requires that transportation revenues be spent only on transportation purposes  Monthly funding of debt service on a 1/5th and 1/10th basis for semi-annual interest and principal, respectively

2019A CTF Credit Highlights

 Commonwealth’s CTF and GANs credits are among the strongest transportation credits in the US  Both credits were created to provide investors with significant debt service coverage and legal protections

 Two-pronged ABT providing 4.0x MADS coverage  History of success in obligating Federal funds  No appropriation of Federal Highway Reimbursements is necessary  Debt service deposited with trustee one year in advance of payment  Double barreled security provided by Federal Highway Reimbursements and Net CTF Pledged Funds  Projected debt service coverage is estimated to be no less than 12.8 x (assuming both Federal Highway Reimbursements and Net CTF

Pledged Funds)

2019A GANs Credit Highlights

*Preliminary, subject to change

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Transaction Timeline*

The financing schedule calls for the CTF 2019 Series A and GANS 2019 Series A bonds to price and close in November

November 2019 Financing Schedule*

Date Event November 5 Mail Preliminary Official Statement November 13 Retail Order Period GANs November 14 GANs & CTF Revenue Bonds Pricing November 21 Closing

S M T W T F S 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30

*Preliminary, subject to change

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Appendix – Projects to be Financed

26

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Massachusetts DOT Rail Enhancement Program

27

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Green Line Extension

 Extend the existing MBTA Green Line by utilizing two distinct branches within the existing railroad right-of-way: a “mainline” branch which will operate along the existing Lowell commuter rail line, beginning at a relocated Lechmere Station in Cambridge and traveling through Somerville to College Avenue in Medford; and a branch line

  • perating within the right-of-way for the existing Fitchburg commuter rail line leading to Union Square in Somerville

 The Green Line Extension project includes the following elements: − 4.4 miles of new Green Line track and relocation of 4 miles of existing commuter rail track − Relocated Lechmere Station anchoring transit-oriented development in Cambridge − Five additional new stations in Somerville and one new station in Medford − Roadway and traffic improvements − Reconstruction of bridges and construction of viaduct structures − Catenary, signals, communications and power to support the extension − Extension of the existing Somerville Community Path − 24 new Green Line vehicles − A new Green Line vehicle storage and maintenance facility  Proceeds of 2019A CTF Bonds will be applied to the Commonwealth’s share of the costs of the Green Line Extension project related to certain contracts already underway

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Red and Orange Line Improvements Program

 Program includes procurement and replacement of new Orange Line and Red Line vehicles to improve reliability accessibility and energy efficiency as well as associated improvements to maintenance facilities, track and signal infrastructure to accommodate the new fleet and to address the state of good repair needs of the MBTA  New cars will feature increased capacity and additional seating, wider and electrically operated doors, accessible areas in each car, LED lighting, updated HVAC systems and improved communication systems  The Red and Orange Line Improvements program includes the following elements: − New Vehicles:

  • 252 new Red Line vehicles
  • 152 new Orange Line vehicles

− Orange Line infrastructure improvements:

  • Wellington maintenance facility improvements and expansion
  • Rehabilitation of existing test track for Orange Line vehicles
  • Improvement and expansion of tracks 35-38 at Wellington Yard
  • Wellington Yard upgrades
  • Orange Line Signal Upgrades

− Red Line infrastructure improvements:

  • Cabot maintenance facility improvements
  • A new test track
  • Cabot Yard upgrades
  • Codman Yard rebuild
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South Coast Rail Program

 This project will offer a reliable transit connection between southeastern Massachusetts and Boston. Riders will be able to take a 1-seat trip – no transfers needed – from Fall River and New Bedford into Boston. Taunton, New Bedford, and Fall River are the only major cities within 50 miles of Boston that do not currently have commuter rail access to Boston. The South Coast Rail Program will include: − Extending the Middleborough/Lakeville Line west, and creating New Bedford and Fall River Lines − Extending the New Bedford Line south to connect more communities to the New Bedford and Fall River Lines − Upgrades, replacement and/or improvements to culverts along lines